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Bien) A CHEMICAL LOVE STORY ALEAAN DER Fa AN IS SHIULGIN Cx SPU LG
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This is the search that has been part of human life from the very first moments of consciousness. The knowledge of his own mortality -…
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my entire self drawn rapidly into a tiny point which kept shrinking, until it could shrink no further, at which time the microscopic point…
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Hello, dear friend, I salute you with respect-humor-love. It is a pleasure-with-laughter-joy to encounter you again. That which greeted me…
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grew older it came less and less often, until around age twenty-five, when it happened only twice in one year, then never again. The…
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the middle of another noisy party, when he began describing the "strange vision" that he, too, had had ever since he was a small child.…
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Paul was caught in a terrible ambivalence, having tried throughout his failed marriage to father a child, finally coming to believe that he…
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When she went to get a towel for me, she stopped at the side of the bed and muttered something that sounded like, "Jesus!" Having given me…
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of which he regarded as necessary evils to be endured on the way to the only thing that mattered - becoming a psychiatrist. I was familiar…
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expect their children to have any interest in, anything that did not have an obvious application to medicine. Having drawn and painted all…
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"How ya doin', Sam?" "I thought you'd like to know," he said in his usual abrupt way, tearing apart a piece of sourdough bread, "I have…
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got your sea-legs. It's always best to be outside, in natural surroundings, during this kind of experience." Suddenly, Sam was no longer…
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from them. We have, in our own society, learned to deaden physical pain and debilitating anxiety with the medical use of drugs which have…
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I remembered what he'd said in the cafeteria, about vomiting. I felt a sudden shortness of breath, as I stared at the jar. "Sam, what…
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Suddenly, Sam was coming through the archway, running across the wooden floor. He disappeared into the bathroom. I heard the sounds of…
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I broke the silence with something else I was seeing, "I just realized, Sam; you really are the outsider, aren't you? And that's the way…
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the silence was, and how I wouldn't mind if it went on forever, and that I wouldn't mind if it were broken, either. There simply was no…
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He went over to the bay window and squinted through the blinds. "Sunlight's fading. Got a raincoat you can take with you? The radio said…
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mistake of passing judgment on the conduct of a life I knew nothing about. Oh, boy. Just got slapped. I remembered my mother telling me…
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It's some kind of life-force; is it what they call the etheric, the life-body? Is there some way I can see that continuous movement all the…
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I looked into his eyes and said, "Thank you, Sam. Thank you very much for giving me this day." He blinked, then rubbed his nose vigorously,…
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the body of the beloved. I didn't have to think about whether the ground was sloping up or down, or whether there might be stone or stick…
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when the pain stopped." We walked in silence for a few moments, then Sam said, "I remember seeing a dead bird lying in the grass, once, in…
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century, once the Intercontinental Railway had been built and the Chinese laborers were no longer needed, they were increasingly portrayed…
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darting fish and became all the little silver bodies at once. How is it I'm aware of being completely me - J can locate my Self, my center…
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There was no one else in the hall. Around us were low walls of polished stone, topped by the glass exhibit cases; there were metal strips…
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raincoats, at the people leaning over the railing around a huge depression in the floor over which a great pendulum was slowly swinging a…
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reflections here and there from the bottoms of lotus leaves. An occasional blur of orange-gold in the depths reminded us that this was a…
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I averted my eyes, then tried looking again, amused and annoyed at the same time. I asked him if he knew why the colors hurt the eyes, and…
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I said, what I did, and I couldn't remember any time in my life when my thought processes had been sharper or clearer. I had absolute trust…
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"T'm used to it. Just hold onto me." I grasped his hand and kept an eye on the stoplights, and when the light ahead of us turned green, I…
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funny, tremendously loving part of God was, thanked it with all of my being, and fell asleep. CHAPTER 18. THE BEGINNING Shura and I met on…
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Berkeley, as usual, was ahead of everywhere else in making it a cause. You could still expect to find ashtrays in most homes in San…
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I said, "Oh, dear, how long ago did she die?" He said about a year ago, and I made a small sympathetic sound, thinking/ I wonder if it was…
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power without being punished." I have stated some of my reasons for holding the view that psychedelic drugs are treasures. There are…
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managed to do it that way/ because it's paid off for everybody. I mean, my children haven't really had too bad a time with the divorce." I…
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From the driver's window, I looked at the tall, brown-jacketed figure and said, "I'm very glad to have finally met you and I hope we meet…
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and suffered bouts of guilt when I realized how often the kids picked up after me. The only trouble they gave me was ina tendency to silly…
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pillows scattered around the floor. I sat down on a dark brown velvet pillow close to an archway, arranging my long skirt gracefully on the…
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easy. We don't even know whether Ursula is in California, do we? When the turbaned Indian person was well launched into his presentation, I…
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said, "You know, that's probably the strangest part of this whole very strange business; Ursula has told me, over and over, that Dolph is…
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I said, "I would love to hear about your work." He began, "Do you know what psychopharmacology is?" "Not really." "I think I told you, the…
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room about a hundred yards behind my house. It had been the basement of my family's first home on the property. The house burned down one…
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Shura leaned back, his chair creaking, "Well, while I was still working for Dole, I was invited to give a lecture at Johns Hopkins in…
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It caught up with me, all of a sudden. Here was a man I had liked from my first sight of him, was liking more and more - in fact, I was…
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THE PROCESS OF DISCOVERY The second most often asked question, after, "Why do you do the work you do?" is: "How do you determine the…
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Know what you're using, decide just why you're using it, and you can have a rich experience. They are not addictive, and they're certainly…
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speaking the absolute truth, then got my coat and quietly let myself out. CHAPTER 19. SEDUCTION On the night of the party, I dressed in…
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a small river which flowed past us, down below. For parties, it was wonderful; for daily living, less wonderful. There was no insulation…
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Okay, I'm obviously trying to be amusing and maybe even shock him a bit, but now he can assume I'm not a swinger. I continued, "That woman…
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me and said, "I feel total, complete disgust for all tests of intelligence, and only limited patience with the people who give them. When I…
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knew where the bathroom was. I caught sight of Shura often enough to reassure myself that he hadn't left the party. When I had done…
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that emerge when people have had quite a lot to drink and have forgotten to be self-conscious. Shura was sitting with Stan, hands clasped…
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"I thank you for the invitation. It was an excellent idea, and if you hadn't come up with it, I'm sure I would have found a way to suggest…
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just have to dive in and bombard you with questions, if you can stand it?" I looked at him, suddenly anxious. Maybe he didn't want to…
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"The most I can ever do in regard to a drug," he continued, a shade more gently, "Is establish what appears to be a relatively safe level…
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there is still only one way to do it, a way that minimizes the risk, while maximizing the quality of the information obtained. I take the…
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I said, "Sure, that's a perfectly respectable objective. But there's another one, isn't there?" If he's the kind that gets irritated…
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" on. "Like Huxley." "Yes. Unfortunately, there aren't many Huxleys around, ever. But each voice counts. All I can hope for is that…
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"No. She says she'll have to make the final break with Dolph at just the right moment, when he's calmer, when there's less risk of his…
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But during her last year, for some reason, she got up the courage to try. One day, she came to me and said she'd like to take mescaline.…
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His right hand moved to my waist and pulled part of my blouse out, then I felt his fingers on the back fastening of my bra. I thought. Oh,…
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"Thirty! Good heavens. Any particular reason - a shock of some kind?" "No, no shock. And no drug, either. At that time in my life, I was…
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The hand took charge. It explored and insisted. I suddenly felt vulnerable, because I knew he was aware of the response inside me, that he…
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‘oing to do the same. Please don't give me an answer, because I know there can't be one, right now." going I looked at the fine line of one…
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CHAPTER 20. DOOR CLOSING The next morning, while I cooked a breakfast of scrambled eggs and toasted English muffins, Shura played my piano,…
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world stays the same and you learn to roll with the changes. If you don't," he paused to sip coffee, "You waste a lot of energy and a lot…
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compounds that are orally active at levels much below 50 micrograms. And I have discovered that the very few drugs that are active in the…
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"Sorry," I said, "I was listening to you, but a nice memory rose up suddenly." I waited for him to ask me what the memory was, but instead…
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"Thank you for telling me, Shura. I don't know what to say except that I can't wish both of you luck. I wish myself the luck, to be honest,…
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CHAPTER 21. DOOR OPENING I thought of it as The Closing of the Door, complete with capitals. It was the first time I'd cried because of…
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She tried marijuana for the first time, at a high school friend's party, and got very sick on the lawn; that was the end of her…
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Much later, during my marriage to Walter, I read the newspaper accounts and watched the television coverage of the riots ina suburb of Los…
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When Christopher was a grown man, beginning his own family, he finally told me what Irene had done to him, how she had treated him,…
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half watching the evening news on television, when the phone rang. With the sound of his soft hello, my automatic pilot switched on and -…
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"Fine. See you when you get here." When he finally stood in the doorway, I went completely quiet inside. The scurrying around of the…
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"You're sure he knows his wife is with you, when she's away?" "Oh, there's no question about that; he's made references to her coming here.…
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I brought him a large pad of paper and a pen. He wrote rapidly for a few minutes, then tore the page off and handed it to me. I said, "What…
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early in the experiment, and is the prelude to further developments. Each member of our research group has his own individual form of…
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CHAPTER 22. WINDOW I missed the road, the first time. It was tucked right behind a blind corner formed by an outcropping of rock and scrub.…
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The kitchen was comfortably large, with a linoleum floor so old its original pattern was lost in a general browr-ness. It had been swept…
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At the far end of the room was a stone fireplace; firewood was piled to one side and, next to it, some neatly stacked cardboard boxes. On…
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"I thought I told you that I'm what is known as an expert witness, in cases involving drugs - illegal drugs - and sometimes the police…
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across the Bay. I'd never been to any of the towns in Contra Costa county. I couldn't remember even seeing Mount Diablo before, except on…
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I asked for what I wanted, since there seemed no reason not to, "I wonder, is there any possibility of my - of taking one of your…
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"Yes and no. It had that effect on me, in a mild sort of way, but it had a very much more important effect on Adam, and I gather on most…
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"I would be most honored, as a matter of fact," said Shura. "Do you always call it MD-whatever it is. Sorry." I did the remorse bit,…
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All right, Ursula, go. This is my day now, and Ire's mine, for just a little while. Shura led me out of the kitchen, back into the warm…
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"Then, a few years later, there was another administration, another postmaster. He came out and said, "You can't just live on a road;…
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experience," in the terminology of the psychiatrist, Abe Maslow. It cannot be repeated at will with a repetition of the experiment.…
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I'd like to see that photograph. Probably his wife. It looks old, sepia tint. Maybe it's his mother. I'm not going to move from here,…
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He's watching, listening, noting everything. He's relieved that I'm okay. He cares and he wants this to be good for me. "It's a very lovely…
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other living things, the world, and whatever drives the universe. It's the First Commandment for my life, and although I don't understand…
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me, whatever happens, it'll be all right." Don't know where that certainty comes from, but it feels true, so it's okay to say it. He…
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Shura was listening intently, then - at a pause in my tale - he suddenly jumped from his chair, saying, "Hold it a minute; I've got to…
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my world differently. There was still the peacefulness within me, and a clarity to whatever I looked at, inside myself and outside. I was…
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Shura said, "I was hoping you would. I like you very much, too. For whatever that's worth to you." "Thank you. It's worth a great deal." I…
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- she didn't trust condoms. What happened was that we gradually - love-making just happened less and less often. We began to withdraw from…
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"We irritated each other too often, Helen and I. We argued a lot about little things, things not worth arguing about. It was a reflection…
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"Not really. She wanted to like it, but this kind of life just wasn't her cup of tea. She was a city girl at heart. That's just the way it…
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possible in this kind of exploration. The subject may well be promoted into an altered state of consciousness, and I consider the idea of…
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"You don't mind?" "No, I enjoy what it does give me, and since I take it these days only with other people, I also enjoy the experience of…
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I thought of pork chops and mashed potatoes, and replied, "Not the most alluring thing in the world, exactly." He grinned as if I had…
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"Of course I will," I promised him, "I have great respect for my own health and safety, believe me. I'll come right back here if there's…
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CHAPTER 23. THE GROUP Late the next morning, Shura called to ask how I was feeling. I said very well, thank you, adding that I was still…
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scared to death. In a few minutes, I would be meeting Shura's best friends; they would inevitably compare me with Ursula - the lovely,…
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Ben said, "Welcome, Alice! It's a pleasure to meet you," sounding as if he meant it. His voice was resonant and warm, with an undertone of…
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his head thoughtfully, then said he would take a chance with seven. Shura scribbled on a large piece of paper, then announced, "As for me,…
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eyes. He flashed a grin at me, peered into his own glass and shuddered dramatically, making a sound of strangled horror, then looked back…
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Leah reappeared with a stack of blankets of different sizes and colors, and George said, "Ah, thank you, thank you. I can use a couple or…
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"Well, this is why we have a research group," Shura said, hands in the pockets of his corduroy jacket, "But I must say, this one is hard to…
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PIHKAL Part 1
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There is the same understanding in regard to feelings of anger or impulses of violence, should they arise. This allows for an openness of…
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as - inhis words - a lifelong student and critic, I as a person who had drawn and painted all my life. We talked eagerly about the Brundage…
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When ifs time to move on, she explains - and probably believes - that she's ending the relationship because she couldn't live with the…
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shrugged, "I may be wrong, of course; Ursula may yet surprise us both. But I don't think so. I don't think I'm mistaken about her." He…
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some things that've been happening recently - difficult interactions with a certain professor, a couple of good discussions I've had…
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We laughed Shura pointed his pen at me, so I took a deep breath and gave my report, "I was off baseline, but not very much. Even after the…
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Shura hugged me and said he would be in touch soon, adding, "Thanks for being so courageous and going along with things so gracefully."…
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"I suggest we try a modest dosage level, this first time," he continued, unabashed, "I think eighteen milligrams should give you a…
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note that the idea of Ursula having been here before me didn't seem important. That was another reality, and it had nothing to do with this…
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everywhere. We were The Node, that to which all lines of life go, that from which all lines of life come. There was a sense of gold…
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telling him about it. I had learned something, but it would take some time to figure out exactly what. Some parts of it are obvious. If you…
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BOOK I: THE LOVE STORY
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which I expressed freely. His back was my playground, as I showed him what could be done with the tips of fingernails running lightly from…
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Shura, wearing his dressing-gown, stood grinning at me. As I frantically grabbed for my towel, he teased, "I thought we were going to have…
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"It isn't shocking to me," I replied, "It's what they call 'bondage,' isn't it? From what I understand, lots of people enjoy that. I read a…
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coming out of that far shadowed place - rising toward me with exquisite slowness - an immensity of petals unfolding, dark purple to…
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Masses of deep orange, edged with red, flooded my mind. I opened my eyes for a second to see Shura's head rising from the pillow as his…
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"You know perfectly well I did." Closing my eyes, I saw a multi-colored dragon with jeweled scales. Its wings were black, tipped with gold,…
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"If he was acting, it was the kind that gets you all sorts of prizes in that Hollywood operation - what's it called - ?" I nodded…
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except for the business and sports sections, which I usually ignored. When we were through, he sat back in his chair as I poured more…
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"Well," I said, hesitatingly, "As a matter of fact, I have a lot of sympathy with that view, and I'd like to explore it a bit." "Of…
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minutes?" I told him I wouldn't mind at all, "As a matter of fact, I'd rather like to be by myself for a little while and pay attention to…
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Part One: Shura's Voice CHAPTER 1. THUMB I was born on June 17,1925, in the progressive city of Berkeley, California. My father was…
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perspective. With familiarity, I thought, the mind tends to notice only certain pieces of furniture and ignore others. One moves past this…
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"Of course it's not inconceivable," Shura said, "Everything that exists, not just plants, but rocks, animals - everything we see and…
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like that. I had no idea that sort of thing could happen in a lab. It puts a completely different light on lots of things. Did you ever…
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I felt the aura of the Grail, then a flood of exquisiteness roared toward me, and I was left floating in a sea of soft blue light. I…
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fierce and strong lived, but I was in touch with it only in times of crisis and loss. One of the few times the strong thing within me had…
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But sometimes it got to me - the knowledge that I was the fill-in, the second-best - and my deeper self, less amenable to clarity of reason…
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didn't find this aspect of him unappealing. It not only gave hima necessary strength, but was - in my view - the kind of elitism that many…
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desk and I would have to take care of myself for a while. I assured him I would be fine, wondering to myself what was wrong. While I…
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room, not daring to sit down yet, because I suspected that all this was actually some kind of displacement of anger at me, or anger at…
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anything; I lose all feelings of trust. There's only anger, at everybody - myself most of all. Everything I'm doing, everything I plan to…
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Most of my impressions of my father came from stories told and retold to me by my mother. There was a trip we had all taken when I was very…
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together/ packed them in the shopping bag I'd brought them in/ and put the bag next to the couch. Then I sat and focused my eyes on the…
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elaborate sarcasm and sharp-edged teasing, but the Siberian Wastelands never overtook him in the old way again. Eventually, I discovered -…
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That's all you can do." Shura went on, "I kept the good part for last. Ursula said something that makes me feel a lot more hopeful. She…
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"Anyway," he continued, briskly, "Dante and Gemina Sandeman live in a little town called Gold Tree. They moved out there several years ago…
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"Tell me about David." "Sure," replied Shura, "I've known him for years. He's in his late thirties, though he looks barely drinking age,…
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When we'd finished eating, I poured Shura a glass of red wine and myself some white. I asked, "By the way, what are you planning to give us…
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or almost everybody - should have the experience. And he certainly did his level best to contribute to that goal, believe me." "How did he…
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" way. "What happened?" "He became very paranoid, sometime in the '70's, and got it into his head that somebody was going to bust down his…
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I smiled. He went on, "Ginger is a superb painter/ by the way. She began painting only a few years ago - watercolors. They live in the high…
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sand-colored brows, held an expression more anxious than curious. He shook my hand firmly and said in a voice that cracked a little at the…
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That did it. Apparently the government man simply hung up his jock, realizing that no one but a genuine American citizen would display that…
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bit daring, this time, something that will appeal to the hard-head, macho types especially - and there is certainly no dearth of them in…
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"John, five hundred," said Shura, busy writing. Dante was next, frowning again, "Well, since we can take a supplement later, if we need to,…
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I asked Shura my question, and he nodded, "Yes, that's a very interesting fact about mescaline; it doesn't matter what form you take it in,…
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lettuces and bright-red tomatoes heaped in a woven basket, alongside loaves of bread - one satin brown, another a braid of creamy beige,…
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I asked her how she was feeling, and she replied, "\ think I took just the right amount. I certainly wouldn't want to go higher than this,…
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Shura said, "It's about one and a half hours, and we've still got a bit of climbing to do before we level out. Are you comfortable so far?…
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Opening kitchen cupboards and gathering together what | needed, I noted my thoughts drifting, and realized I would have to focus…
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know I was all right. He got up and left the room. In a minute, the sound of music came through the speakers from the back room. Gregorian…
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I was looking through a book of fairy stories with illustrations by the great enchanter, Arthur Rackham, and everyone around me had been…
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outside. I looked around at the closed eyes, and gratefully closed my own. I was aware, first of all, of the enormous energy in my body,…
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ego-awareness (if that's what it's called) came about, I interacted less passively with other people. I was a child prodigy. I never…
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everything that was going on in everyone else all the time. We would be a group consciousness, as the rest of the life forms on earth seem…
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Some of the group decided to try the outside again. George expressed an interest in checking the soup, now that he had been reminded of it…
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Shura glanced at me thoughtfully, then looked away again, "You're probably right. When you're little, you live in what we would call a…
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Shura had taken my arm and was leading me up the path to the lab. We walked slowly, in silence, stopping every few steps to look at an…
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I've never told anyone else what I just shared with you about my childhood. You may be right, that the only real difference between me and…
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read George's face and reached the same conclusion. I sat down on a floor cushion and watched Shura quietly move through the room, looking…
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CHAPTER 29. THE LETTER Shura often gave me Ursula's letters to read. He knew that seeing her writing for myself gave me an independent, if…
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this man's voice did not meet the expectations raised by the rest of the divine company. Surely, they will not give to him such an…
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line. It's just not -1 can't fit it into the picture. Nothing fits the picture properly. None of it makes sense." Ursula goofed. What now?…
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What I am attempting to do, in writing this, is to tell you that I believe this man is worth the pain I feel in knowing that I cannot have…
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basements. My mother called it hiding, but I thought of it as escape. From what? Well, for instance, from having to practice the piano.…
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don't really love him, I'll do everything I can to fight you for him! When Shura had finished reading, I said, "I'm just going to leave the…
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"They're among my oldest friends, and we used to do a lot of exploring together. Not as much, the last few years. Terry's a psychologist at…
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I got up and turned on the television. The Discovery channel, one of my favorites, was showing a documentary on Nepal. I watched it with…
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toward me, and I knew what it was. I heard the choking sound in his throat and its explosion into the long, long roar of completion. I…
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CHAPTER 30. ENDING It took two weeks for Ursula's reply to arrive. She wrote two pages and enclosed my letter, demanding an explanation.…
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"Yes, of course it's all right for you to ask it, and I have to pick up my things, so I'll be out - when? Friday evening as usual, or…
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The next morning, over our coffee, Shura looked at me with a mixture of feelings in his face - happiness, misery, wistfulness - and asked,…
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And those diagnoses are usually made by men, aren't they? Which should make them slightly suspect. After all, Walter told me early in our…
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What about the part of the - God, the It, whatever - that kills and destroys? "It's there in the service of life, to keep the cycle going.…
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Js there any other way for me to see all this? Any way to make it easier? "Life is the One telling stories about itself to itself. It is…
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stamp exploring adventure, and it was always filled with marvels of strange faces and strange country names. I don't think I said…
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That was the Whole. Shura came in. He was in his dressing gown and his feet were bare. His hair stood out from his head as it always did…
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I've thought of it again, I'll tell you and you can pass it on to Dante." "Good," said Shura, "But before you begin, I need to empty a…
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Shura's eyes squinted at me thoughtfully, and he nodded. After a moment, he said, "Thank you. I'll tell Dante, if he doesn't already know…
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great deal of redundancy in the system. With several of the amino acids, the first two nucleotides define the amino acid, regardless of…
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related to our Twosies ina faraway place, ina time long ago, but carried within it that third nucleotide potential which allowed, over the…
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In the intimate warmth of the bed, holding me for what he believed was the last time, and what I hoped would not be, but had to allow might…
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Finally, the angry inner voice subsided and the tears came. My Observer sighed with relief, knowing that the sobs and aching ribs meant…
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CHAPTER 31. VOLCANO When the children came home from their weekend with Walter, I told them, "I've got some grieving to do. The German lady…
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"No appetite. Underneath the pain, I found a knowledge of the rightness of what's happening, and - unexpectedly - a sense of joy! Don't…
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They said yes and sure and okay, we'll take care of ourselves, don't worry. I went to the kitchen and got a glass and a bottle of cranberry…
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My violin teacher was a Russian gentleman, a compatriot of my father, and connected with the Orthodox Church. I had to play in recitals in…
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I closed my eyes and felt the looming, blistering shapes of the emotions churning inside me; there was the rage, the wracking sorrow and…
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then I'll shut up. By the way, I'm feeling very all right." I told them about taking MDMA (they had already heard me talk about my…
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I told him the little story about taking the MDMA, leaving out the worst of the rage and saying nothing about manila envelopes and…
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CHAPTER 32. TRANSITION It was Thursday evening when Shura phoned me. His voice was strained. He told me that the night before, not having…
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"Oh, of course," I said, suddenly remembering, "You thought maybe murder and suicide." "I was beginning to be really terrified; I was…
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final letter to the German Lady. This one, she won't send back to Shura. Ursula: This will be the last time I write to you, and I do so…
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you knew it well enough to assume that he would stay yours until you chose to come for longer, if you wanted to. And there, in your home,…
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Sunday, on the phone, he let the bitterness come through. He said, "I don't think I'm going to allow that kind of thing to happen to me…
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affairs with married men? "Shura," I asked, "This is just an off-the-wall question, but do you have any way of knowing whether she's ever…
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A window has widely opened to you, a soul-window, a love-window, of graceful being - being together. A common space of breathing, of light…
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up with answers at test time without having more than glanced at any of my books, relying only on what I'd learned from the blackboard and…
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this life, through our deep love, we have the real chance of changing this by bringing it out into the open. We have broken a karmic…
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"Please say hello to them from me?" A shade more warmth, this time. I replied that I certainly would, and we said goodnight. All right. He…
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get allergic to everyone connected with it; you don't want to be around people who remind you of what you went through - at least for a…
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CHAPTER 33. RESOLUTION By the end of the second week, Shura hadn't called and I was feeling grim. I kept my emotions repressed, on hold,…
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"I need to ask you," I said, carefully, "How long are you inviting me for? Since this is a new chapter, I gather, one doesn't want to - ah…
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belong only to my past, and I dared not expect it to be otherwise. He had invited me here, this weekend, and that could mean he wanted us…
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grin - "Is for sure." As I took a bath, my thoughts were a confused mess. One thing returned to my mind several times, and that was the…
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LSD in it (Shura had explained that tap water contained chlorine which would kill LSD immediately, as would strong light), we sat in the…
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was time to just be who I was and let myself feel the emotions, including laughter, because to do otherwise was to be untrue to myself,…
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I moved up and lay beside him. The long fingers began lightly stroking, and as I looked past the big head to the ceiling, I saw against the…
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FOREWORD NOTE TO THE READER SEARCH FOR A TITLE THE PROCESS OF DISCOVERY BOOK I: THE LOVE STORY Part One: Shura's Voice CHAPTER 1. THUMB…
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in the middle of the anti-U-boat campaign, in the middle of the war. We had just finished making an anti- submarine search in the area of…
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was a sort of experiment, asking them. I'll admit it wasn't the nicest thing to try with old friends, but I made a bet with myself, a while…
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with me, because this weekend off and on stuff is ridiculous, and besides, you're not a bad kid, everything considered, and I probably…
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CHAPTER 34. THE FOURTH On the 4th of July, 1981, in response to approximately 80 invitations to a picnic at the Farm, 67 people arrived.…
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summer. We had laid out old Persian rugs and some big floor pillows, and when people asked what all that was for, we explained that later…
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Now you are two bodies/ But there is only one life before you. "Go now to your dwelling place, To enter into the days of your togetherness.…
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I hugged each of them and said many thanks for having done their part so beautifully. "Well," Ann remarked, as they turned to go back to…
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Part Three CHAPTER 35. AACHEN Both Voices (Alice's voice) A few weeks after the wedding, Shura was given the opportunity to attend a…
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A very long plane ride later, leaning out the window ofa hotel on Piccadilly Square, I breathed in the smell of London - sharp, sooty and…
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Soft candlelight reflected deep orange on the polished tops of the pews facing the Madonna. Above the huge pillars loomed comfortable…
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the well was a small bronze soldier on a horse. An excited little girl called to her parents to watch as she bent and straightened the arms…
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Then came a big monster of an ambulance which took me from Liverpool to Watertown and delivered me to a white-coated Army staff. A young…
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I stretched and yawned, "Right now's okay with me. We shouldn't be up too late if we take it now." Shura unpacked his set of vials and held…
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like a pyramid, sort of. I don't even know whether it's good or evil; it's just huge and strong. That's the closest I can get to it. Like a…
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How fantastic!" "Well," said Shura, pulling me down beside him, "Now that we've got that figured out, how about some very personal…
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beginning to feel; I saw that, before long, they would leave him alone in his circle and go to some other place together, because there was…
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When Theo visited the Farm on Sunday afternoons for a few hours, Emma usually accompanied him, settling gracefully into the role of…
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on these days?’ and when Shura told him - you know, very casually and completely straight-faced - about the TOMs and TWATs, there was this…
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I returned to the patio, with its soft sunlight, and stayed for a while, smoking, enjoying the isolation, while keeping track of the…
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writing on this." "All right," said Shura. He turned to Ben, "You, Benjamino?" "I second that - about the de-stressing quality - and for…
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Theo looked up, "What do you think? Has Ruth come down?" "Nope. I think I'm going to tiptoe up there and find out what's happening. By the…
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We're holding you, so you can't fall." Shura, on the other side, said, "Come on, George. It's just a few steps. You're absolutely safe."…
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A fraction of a gram of sugar had rendered me unconscious, because I had truly believed that it could do just that. The power ofa simple…
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I start wondering what I'm going to do if he doesn't come out of this, a little voice inside tells me not to worry. It says just be…
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Shura asked, "Would you be willing to take this material again?" George didn't hesitate. "Yes, I'd certainly take it again, but at a way…
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"That did cross my mind, too, at one point," admitted Ben, and Shura grimaced in agreement. She went on, " - and that's when I got the…
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He looked over at George, "And I suspect that you have a strange and wonderfully idiosyncratic sensitivity to 5-TOM which there was no way…
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CHAPTER 37. FUGUE (Shura's voice) The word "fugue" has always had a most pleasant sound for me. It is a French word meaning flight/ or…
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confusion. On the other hand, in my fugue state, even though the landscape in all directions was completely familiar, the sense of rotation…
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"The numbers on the digital clock are equally worthless. They can give me absolutely no insight as to what time it is at the moment. Sure,…
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I had to put on San Francisco clothes (a white shirt, a non-outrageous tie, a jacket, and clean socks). Brute subtraction (present time…
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Twice, since then, basically identical experiences have occurred, but in shorter time. The most recent lasted only twenty minutes. Somebody…
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CHAPTER 38. CRISIS (Alice's voice) SUNDAY This is the story of a major alteration of consciousness which occurred because, apparently, it…
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CHAPTER 2. MESCALINE Mescaline: a magic name and a magic compound. My first encounter with this word was just after World War II, when I…
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"Well," he cautioned, "As I told you, I don't honestly expect we'll get any activity, but you never know. You could have a threshold, if…
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go to when we return from being away. I had never before seen it present itself the way it did now - hard, unfriendly, almost hostile. I…
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mountain were very much present/ but I could see neither beauty nor ugliness anywhere/ and I felt no personal connection to any of it.…
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"Uh-huh/ it sure does." "You going to be all right?" "Oh/ yes. I'll do the dishes/ then just relax and watch TV for a while and keep myself…
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before I told him, "I'm still on, honey." He frowned, "What do you mean? You're still feeling something from yesterday?" "I know I was…
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Jesus, I can't cry now! I've got to hold on until he's out the door. There's nothing he can do, and he'd just worry. I squeezed him back…
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hyacinths and daffodils - and knew that I was tuning in to a pure consciousness of unlimited intelligence and absolute clarity; there was a…
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of its parts. Okay, this is not the Mind of God. On the other hand, what if the answer I got before was wrong, and this is the true nature…
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Do you hear me, you damned monstrous son-of-a-bitch? I say NO to you! I DENY YOU! I realized that tears had been flowing down my cheeks for…
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continued, and I resumed my rocking. All those thousands and thousands ofyears of human beings trying to survive, everywhere on the planet,…
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color. The rainbow had always provided me with all the hues I could respond to. Here, suddenly, I had hundreds of nuances of color which…
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The ringing of a telephone reached me through the back door. I spilled the cat off my lap and went inside to the office/ hoping it would…
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I said Oh. "Next thing," continued Adam, "What you're going through is a process. You don't have any way of understanding what it is or why…
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When he had finished with letters and bills, I sat down at the table and gave hima shortened version of the day's struggles, and described…
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I remembered the pressure of that unseen awareness, an almost physical sense of being pushed at, as I stood outside the back door. " On the…
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"An integrated, complete human being, of course, uses all of himself - emotional, intellectual and spiritual - and does not fail to…
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I lay on my back, staring at the ceiling, as Shura settled into sleep, his hand occasionally twitching slightly, in mine. So the White Mind…
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I said, "Whatever this damned thing is, there's no question that any standard-issue psychiatrist in the world would label it psychosis,…
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When I focus like this, talking with him, there's less noise from the thought-parade. I asked him, "Can you think of any possible…
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a sort of compulsive surveying of human history, images of people from prehistoric times up through the present, creating cities, books,…
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"The hard part," I paused, swallowing, "Is that I'm being bombarded mostly with the sadness, the suffering, the loss of meaning that human…
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CHAPTER 3. BURT In the late 1940's I married a fellow-student at University of California named Helen. We were both active members ofa…
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flow - hadn't fully acknowledged it before. Pain is a sign of imbalance, yes? Or a result of some kind of transition. Transition from one…
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nobody around to tell you ? What would have happened if there hadn't been an Adam for me to call on, someone who knew exactly what to tell…
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hate I was sensing; the most utterly virulent hatred I had ever met in my life. A murderous, contemptuous hatred so intense, my mouth…
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I've been a good mother. For all my faults and mistakes, I've been a damned good mother. There were hot tears on my cheeks. How does that…
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My father had always shown love, warmth and caring. And my brother. Why, I wondered, hadn't I modeled my self-image on their feelings…
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What about the other thing, the hanging judge, I thought? What was I supposed to do with that implacable, searing hatred? Inform it that…
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aphrodisiac. That night, I had my first experience of lucid dreaming. I was conscious, my ego intact, aware that I was asleep and dreaming,…
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WEDNESDAY Except for an energy level somewhat higher than usual, I felt entirely normal. I got into my car and decided I wasn't really…
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THURSDAY I woke up with the sunlight streaming through curtains which were completely inadequate for room- darkening purposes, and my first…
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had gone, and in their place was a dry kind of almost-humor. Thursday was another teaching day for Shura, and he had the Ow! Club in the…
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Not wishing to set up cobwebs, I chose the fish route, and sent off to Van Waters and Rogers for several big battery jars, to the local pet…
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beneath our neighbors' fruit trees, and found myself thinking of the ancient mythical relationship of bees to the archetypal Earth Goddess.…
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imagined. I felt fear only once. Driving off the connecting ramp onto Shoreline highway, I saw in my rearview mirror a man at the wheel of…
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Adam sat across the table from me, watching and listening. I concluded, "A lot of the stuff that's been happening has been really…
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"Sure - lots of names. Psychosis is not among them, by the way. Names don't matter." "But it helps, Adam, it helps to give it a name - any…
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I stayed until I knew that whatever had been crippling me was finally beginning to heal; the psychic noise was calming down, and I was able…
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was trying not to be too receptive to all of it, for the sake of both of us. Beneath all the rest was a layer of serenity, a certainty that…
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FRIDAY Shura got ready to leave for work, promising to come home as early as he could manage. I said I would be fine, that things were…
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"The whole terrible business of victimized child growing into victimizing adult is, to me, a tragic, twisted, stunted perversion of what…
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The wisdom that revealed itself in the instinctual activities of the pair and, later, their babies, struck me with unusual force. There was…
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He said, "I have an idea I'd like to run by you. Tell me what you think." I smiled at him, "Okay, what is it?" "You know how good old 2C-B…
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We spent the next several minutes trying to reconstruct just how much LSD might have been on the end of the spatula, and decided that it…
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SATURDAY When I woke up, I was myself. I was at baseline and I knew I would stay that way. The process/ as Adam had promised, had completed…
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SUNDAY Shura took the DESOXY at the same level, forty milligrams, that he had given me on the previous Sunday. It was, he reported,…
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One May, in the 1980's, Dante wrote an account of a complex and quite extraordinary experience with a drug he and Ginger had found very…
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My own experience is that God is everywhere, the essence of everything that exists, "As near as hand and feet," waiting to join us as soon…
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But no matter what I came up with, they countered and defeated me. I was helpless. I would have to spend the rest of my life in their…
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started in Love. A love so great, so tremendously charged that it was like a huge fiery furnace, brighter than any sun. Suddenly I am…
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A fierce sense of independence wells up, and I remember that the basis of Gnosticism is each individual's right, if not duty, to develop…
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realization. I could amuse myself for hours at a time, if 1 simply wished to sit and look at my surroundings with an open heart. However, I…
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middle of a frantic year of getting and spending. I have never lacked for activities that make demands on my time, but almost all of them…
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The next morning we skipped breakfast, except for coffee, and at ten o'clock, we took the chemical. The walk along the valley floor was…
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CHAPTER 4. TMA It is 1960. Here I am, with my mescaline experience dramatically fresh in mind, a burning desire to explain its profound…
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death is a certainty. Who knows when? Maybe right now. Is this the time and place to close it all off? The Ponce de Leon search for youth…
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between this 2C-E experience and that dramatic one I had weathered in Tennessee over a decade ago. There had been a death thing there, as…
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men sitting in what struck me as ridiculously puffy easy chairs. I asked - a rather silly question, in retrospect - if anyone there was a…
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I survived, but the darkness of the imagery was not easily dispelled. It was all of four days before I was able to get completely out of…
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by the human spirit, wherever I shall find them. And finally, I must admit that I now look forward with total fascination to discovering…
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and try to deduce, with some humor, who it is. Or, rather, who it might have been, that was so insistent on demanding a response. So, freed…
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everything within me too. A complete identification with my environment. And a sense of being at total peace with it, as well. If this is…
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was moving across the road at the last turn. When I came back, I saw that there were dozens of caterpillars [I looked it up] all over the…
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substantially baseline. (17:00) Went to sleep without much difficulty. Next evening, at (36:00) tried a challenge with 30 milligrams of…
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the signing of the Constitution, some ten years following our Declaration of Independence from England, and many of our present inalienable…
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physical coordination. But it was my mental attitude, and responses to, and identification with external stimuli (primarily musical) that…
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However, in the current madness involving drugs and violation of drug laws, it is no longer necessary to convene a jury or - for that…
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finally brought. Very recently, the courts have decided that, after a conviction of a drug-related crime (using the "beyond reasonable…
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a warrant based on this statement. So it turned out to be an LSD lab and there was no methyl amine present. That's okay, since I acted in…
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me that you indeed are." Outrageous. Intolerable. I don't care if the man is the pilot of Air Force One with the President on board, or the…
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the alleged crime. These particulars can all contribute to an increased and inflexible minimum sentence in prison, with times ranging from…
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It is a fact of life that all research today, at the academic level, is supported almost exclusively by federal funds, and ifa grant…
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computer data had apparently been lost. And there was none of the original blood sample left for a re- analysis. It will never be known if…
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Institute of Drug Abuse admits were not valid. In this study done by Research Triangle Park, nearly 4000 households were surveyed, and the…
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sitting out there, ready to go Whoopie! with the repeal of the drug laws. The majority of the population will, however, benefit from the…
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Would you still proclaim, "I don't mind; I've got nothing to hide!" I doubt that there are many of you who feel disturbed about the…
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CHAPTER 39. DANTE AND GINGER AND GOD Document Outline
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internist once every ten years or so, but always with the same pistol (and the same body). It is good to get an objective evaluation of…
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whether his neighbors would find it so or not. He should be free to sit and watch television all day long, if that's what he chooses to do.…
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To which I can only say amen. That's it. See you next week.
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PIHKAL Part 2
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Subject: PIHKAL: The Chemical Story. File 1 of 6 This is part | of 6 of the second half of PIHKAL: A Chemical Love Story, by Alexander…
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20 2C-B; 4-BROMO-2,5-DIMETHOXYPHENETHYLAMINE 21 3C-BZ; 4-BENZYLOXY-3,5-DIMETHOXYAMPHETAMINE 22 2C-C; 2,5-DIMETHOXY-4-CHLOROPHENETHYLAMINE…
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60 DMPEA: 3,4-DIMETHOXYPHENETHYLAMINE 61 DOAM: 2,5-DIMETHOXY-4-(n)-AMYLAMPHETAMINE 62 DOB: 2,5-DIMETHOXY-4-BROMOAMPHETAMINE 63 DOBU:…
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102 MDBU; N-BUTYL-MDA; 3,4-METHYLENEDIOXY-N-BUTYLAMPHETAMINE 103 MDBZ; N-BENZYL-MDA; 3,4-METHYLENEDIOX Y-N-BENZYLAMPHETAMINE 104 MDCPM;…
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145 TA: 2,3,4,5-TETRAMETHOXYAMPHETAMINE 146 3-TASB; 3-THIOAS YMBESCALINE; 147 4-TASB; 4-THIOAS YMBESCALINE; 148 5-TASB; 5-THIOAS…
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1 AEM; a-ETHYLMESCALINE; 2-AMINO-1- (3,4,5-TRIMETHOXYPHENYL)BUTANE; 1- (3,4,5-TRIMETHOXYPHENYL)-2- AMINOBUTANE SYNTHESIS: To a solution of…
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DOSAGE: greater than 220 mg. DURATION: unknown. EXTENSIONS AND COMMENTARY: The extension of the two-carbon chain of mescaline by alpha-…
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CHAPTER 5. BLACKWOOD ARSENAL It was somewhere around 1960 that I met a brilliant neurologist. Harry Bush, who had become totally fascinated…
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**xNever made, as no ***The synthesis got and the * S is for septyl, to distinguish heptyl from hexyl. nonylbromide could be located to…
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2 AL; 4-ALLYLOXY-3,5- DIMETHOXYPHENETHYLAMINE; 3,5- DIMETHOXY-4- ALLYLOXYPHENETHYLAMINE SYNTHESIS: A solution of 5.8 g of…
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QUALITATIVE COMMENTS: (with 24 mg) I first became aware of something in about 10 minutes, a pleasant increase in energy. By 20 minutes it…
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3 ALEPH; DOT; PARA-DOT; 2,5- DIMETHOXY-4- METHYLTHIOAMPHETAMINE SYNTHESIS: A solution of 2.3 g 2,5-dimethoxy-4-(methylthio)benzaldehyde…
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(with 10 mg) There was a rapid shift of frame of reference that made simple tasks such as reading and tuning the radio quite alien. I…
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4 ALEPH-2; 2,5-DIMETHOXY-4- ETHYLTHIOAMPHETAMINE SYNTHESIS: A solution of 2.0 g 2,5-dimethoxy-4-(ethylthio)benzaldehyde (see under 2C-T-2…
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Nothing would stay still; everything was always moving. There was a phase of unabated inflation. The intensity was noticeably dropping at…
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mm/Hg and which did indeed have an aldehyde group present (by proton NMR) but the rest of the spectrum was a mess, and the project was…
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some inspired day. The two-carbon homo-logue of this (2,5-dimethoxy-4-cyclohexylthiophenethylamine) will someday be called 2C-T-5 (if it is…
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5 ALEPH-4; 2,5-DIMETHOXY-4-(i)- PROPYLTHIOAMPHETAMINE SYNTHESIS: A solution of 2.0 g 2,5-dimethoxy-4-((i)-propylthio)benzaldehyde (see…
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"Let's make it!" So I hied myself off to the library to begin unraveling some possible paths to the synthesis. And thirdly, a group of…
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tension and depression, but as the momentum developed, so did the positive effect. My discomfort continued to develop, but I was struck by…
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6 ALEPH-6 2,5-DIMETHOXY-4- PHENYLTHIOAMPHETAMINE SYNTHESIS: To a 300 mL three-neck round-bottom flask set up with a magnetic stirrer and…
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prior sintering at about 98 !C). This was recrystallized from 50 mL boiling 95% EtOH. After cooling in an ice bath, it was filtered, washed…
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County to attend a poetry reading. There I felt myself at baseline and accepted (unusual for me) a little marijuana. And with the utmost…
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7 ALEPH-7; 2,5-DIMETHOXY-4-(n)- PROPYLTHIOAMPHETAMINE SYNTHESIS: A solution of 2.6 g 2,5-dimethoxy-4-((n)-propylthio)benzaldehyde (see…
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somehow didnUt care for his style. I fell apart emotionally, with tears and a feeling of total loss of everything. Everything was visible…
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and it can be written down as a series of perceived phenomena. The notes of the scale. Black quarter notes, with flags at the tops of their…
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8 ARIADNE; 4C-DOM; BL-3912; DIMOXAMINE; 1-(2,5-DIMETHOXY-4- METHYLPHENYL)-2-AMINOBUTANE; 2,5- DIMETHOXY-a-ETHYL-4- METHYLPHENETHYLAMINE…
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(with 25 mg of the RRS isomer) There is the alert of a psychedelic, with none of the rest of the package. Perhaps a bit of paranoia. And by…
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The making of this entailed the proteo counterpart, 1-(2,5-dimethoxyphenyl)-2-aminobutane. Reaction of 2,5-dimethoxybenzaldehyde with…
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deterioration which we all saw as progressively robbing him of both spirit and motivation. Finally, I said Enough! Let's all go on some…
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And the near-pseudo analogue? First, what is near-pseudo? I have explained already that the RnormalS world of substitution patterns is the…
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would produce a threo-isomer, and the other an erythro-isomer. I have named them DAPHNE (who escaped from Apollo by becoming a laurel tree…
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9 ASB; ASYMBESCALINE; 3,4-DIETHOXY-5- METHOXY PHENETHYLAMINE SYNTHESIS: To a solution of 32 g of 5-bromobourbonal in 150 mL DMF there was…
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The aqueous extracts were washed with CH2C12, reacidified with HCl, and reextracted with 2x75 mL CH2C12. These extracts were pooled, and…
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DOSAGE: 200 - 280 mg. DURATION: 10 - 15 h. QUALITATIVE COMMENTS: (with 240 mg) There was a pleasant and easy flow of day-dreaming thoughts,…
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name given for the drug with all three ethoxy groups present in place of the methoxys of mescaline) and the term tetra- mutates into the…
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10 B; BUSCALINE; 4-(n)-BUTOXY-3,5- DIMETHOXYPHENETHYLAMINE SYNTHESIS: A solution of 5.8 g of homosyringonitrile (see under E for…
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either the visual or the auditory area. (with 150 mg) Throughout the experiment it was my impression that whatever effects were being felt,…
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11 BEATRICE; N-METHYL-DOM; 2,5- DIMETHOXY-4,N- DIMETHYLAMPHETAMINE SYNTHESIS: A fused sample of 5.0 g of white, crystalline free base…
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The mental was not up there to a +++, and yet the physical disruption was all that I might care to weather, and exceeds any mental reward.…
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So, for the rest of the way across the Atlantic Ocean, I reviewed, with what modest photographic recall I could muster, the appropriate…
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12 BIS-TOM; 4-METHYL-2,5-bis- (METHYLTHIO)AMPHETAMINE SYNTHESIS: A solution of 9.0 g 2,5-dibromotoluene in 50 mL petroleum ether was…
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solution of butyllithium in hexane. After stirring for 10 min there was added 2.5 mL N-methylformanilide which led to an exothermic…
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DOSAGE: greater than 160 mg. DURATION: unknown. QUALITATIVE COMMENTS: (with 160 mg) I was vaguely aware of something in the latter part of…
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13 BOB; '-METHOXY-2C-B; 4-BROMO-2,5-'- TRIMETHOXYPHENETHYLAMINE SYNTHESIS: To a vigorously stirred suspension of 2.1 g…
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QUALITATIVE COMMENTS: (with 10 mg) I donUt know if it was me this day, or if it was the chemical, but I got into a granddaddy of a…
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14 BOD; '-METHOXY-2C-D; 4-METHYL-2,5,'- TRIMETHOXYPHENETHYLAMINE SYNTHESIS: A solution of 39.6 g…
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filtration and Et2O washed. When air-dried to constant weight, 4.49 g brilliant white crystals of 4-methyl- 2,5,'-trimethoxyphenethylamine…
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analogue would have come out as BOMB, so the idea was dropped. Actually, the concept of naming of drugs with some acronym that is…
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milligrams. It has a ten hour duration, and is both anorexic and diuretic. There have been no visual effects or insights reported, but…
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15 BOH; '-METHOXY-3,4- METHYLENEDIOXYPHENETHYLAMINE SYNTHESIS: To a solution of 30 g piperonal in 100 mL acetic acid there was added 20 mL…
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CHAPTER 6. MMDA I had a number of projects that I wished to pursue in France. I wanted to learn to speak the language, I wanted to break my…
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the salt was a hydrate. Recrystallization from CH3CN, or simply heating to 100 !C in toluene, converted the salt to an anhydrous form, with…
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16 BOHD; 2,5-DIMETHOXY-'-HYDROXY-4- METHYLPHENETHYLAMINE SYNTHESIS: A solution of 0.4 g 1-(2,5-dimethoxy-4-methylphenyl)-…
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membered ring. This might help obscure the hydrophilic nature of the free hydroxyl group and allow the compound to pass into the brain…
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17 BOM; '-METHOXYMESCALINE; 3,4,5,'- TETRAMETHOXYPHENETHYLAMINE SYNTHESIS: To a vigorously stirred suspension of 9.0 g…
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milligram levels, but nothing that can be rated as over a plus one. It can be seen with the two active members of the BOX series (BOD and…
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18 4-BR-3,5-DMA; 3,5-DIMETHOXY-4- BROMOAMPHETAMINE SYNTHESIS: The starting material 3,5-dimethoxy-4-bromobenzoic acid (made from the…
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activity represents the extent of impairment of function, regardless of the nature of the drug producing it. In other words, if you were…
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19 2-BR-4,5-MDA; 6-BR-MDA; 2-BROMO-4,5- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: A solution of 3,4-methylenedioxyamphetamine (MDA) in acetic…
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20 2C-B; 4-BROMO-2,5- DIMETHOXYPHENETHYLAMINE SYNTHESIS: A solution of 100 g of 2,5-dimethoxybenzaldehyde in 220 g nitromethane was treated…
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needles, with a mp of 237-239 'C with decomposition. When there is too much H20 present at the time of adding the final concentrated HCI, a…
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In principle, I thought the synthesis of MMDA should be simple and straightforward. Just take the correct starting aldehyde,…
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Unbelievably erotic, quiet and exquisite, almost unbearable. I cannot begin to unravel the imagery that imposes itself during the finding…
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describing its effects. (1) There is a steep dose response curve. Over the 12 to 24 milligram range, every 2 milligrams can make a profound…
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21 3C-BZ; 4-BENZYLOXY-3,5- DIMETHOXYAMPHETAMINE SYNTHESIS: A solution of 268 g 2,6-dimethoxyphenol and 212 g allyl bromide in 700 mL dry…
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g picric acid in 150 mL boiling EtOH. Cooling in the ice chest overnight gave globs of the amine picrate, but no clear signs of…
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light things, and on and on. This could have been a location of much variation, but it is a possibility that the uncertainties of dosage…
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22 2C-C; 2,5-DIMETHOXY-4- CHLOROPHENETHYLAMINE SYNTHESIS: (from 2C-H) The free base of 2,5-dimethoxyphenethylamine was generated from its…
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CH2Cl2. After washing the pooled organic extracts with dilute HCI and drying with anhydrous MgSO4, the volatiles were removed under vacuum…
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less potent still, and much less explored. Why? Perhaps because chlorine is a gas and troublesome to handle (bromine is a liquid, and…
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23 2C-D; LE-25; 2,5-DIMETHOXY-4- METHYLPHENETHYLAMINE SYNTHESIS: Into 1 L H20 that was being stirred magnetically, there was added, in…
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g. These were recrystallized from 100 mL IPA providing yellow crystals of 2,5-dimethoxy-4-methyl-'- nitrostyrene which weighed, when dry,…
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let the somewhat higher level person take you on the rounds of his peers. After a few introductions over a couple of days, the shift…
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(with 45 mg) There was a rocket from the half-hour to the one and a half hour, from nothing up to a +++. Somehow the intimacy and the…
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after each of the 2C-X's that has served as the prototype. In general, the 2-EtO- compounds have a shorter duration and a lower potency,…
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24 2C-E; 2,5-DIMETHOXY-4- ETHYLPHENETHYLAMINE SYNTHESIS: A suspension of 140 g anhydrous AIC13 in 400 mL CH2Cl2 was treated with 100 g…
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course of 0.5 h. The stirred reaction mixture was allowed to come up to room temperature, then held on the steam bath for 1 h. The reaction…
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approximately 15 mL of residue was dissolved in 300 mL CH2C12 and treated with 200 mL H20 containing 20 mL concentrated HCl. On shaking the…
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amphet-amine homologue is DOET, which is not only much longer in action, but considerably more potent. Several people have said, about…
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25 3C-E; 3,5-DIMETHOXY-4- ETHOXYAMPHETAMINE SYNTHESIS: A solution of 3.6 g syringaldehyde (3,5-dimethoxy-4- hydroxybenzaldehyde) in 50 mL…
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with dilute NaOH, and extracted with 3x150 mL | N HCl. The pooled extracts were washed once with CH2C12 made basic with 25% NaOH, and…
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which is, quite simply, Escaline (or E) reextended again to a 3-carbon chain amphetamine, there is a kind of satisfying closure. A…
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26 2C-F; 2,5-DIMETHOXY-4- FLUOROPHENETHYLAMINE SYNTHESIS: A solution of 76.6 g 2,5-dimethoxyaniline in 210 mL H20 containing 205 mL…
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everything is there but in lesser quantity and duration. MMDA stops barely short of the Olympian Universe of time-ceasing and the…
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stripped of solvent, yielding a residual oil that was taken up in 10 mL of IPA, neutralized with concentrated HCl, and the generated solids…
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27 2C-G; 2,5-DIMETHOXY-3,4- DIMETHYLPHENETHYLAMINE SYNTHESIS: To a clear solution of 40.4 g flake KOH in 400 mL warm EtOH there was added…
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product that had a mp of 141-142 !C. Anal. (C11H1I5NO3) C,H,N. To a solution of 23.1 g flake KOH in 250 mL hot EtOH there was added 61.8 g…
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A solution of LAH (56 mL ofa 1 M solution in THF) was cooled, under He, to 0 !C with an external ice bath. With good stirring there was…
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distinguish, from the recorded notes, any major differences either in potency, in duration, or in the nature of activity, between 2C-G and…
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28 2C-G-3; 2,5-DIMETHOXY-3,4- (TRIMETHYLENE)PHENETHYLAMINE; 5- (2-AMINOETHYL)-4,7- DIMETHOXYINDANE) SYNTHESIS: To a solution of 22 g of KOH…
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isolate with boiling hexane. Reduction with elemental iron gave the phenylacetone analogue which was reductively aminated with…
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mp of 71-72 !C. The mother liquors on cautious treatment with H20, yielded, after EtOH recrystallization, | g additional product. Anal.…
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here where I am safe, and stay with the writing. It does take so much time to say what wants to be said, but there is no quick way. A word…
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29 2C-G-4; 2,5-DIMETHOXY-3,4- (TETRAMETHYLENE)PHENETHYLAMINE; 6-(2-AMINOETHYL)-5,8-DIMETHOXY- TETRALIN SYNTHESIS: To a solution of 49.2 g…
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hadn't yet recovered sufficiently from the last high to hold myself together. Heat swelled in my genitals and rose to my stomach. I felt…
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mm/Hg. There was thus obtained 21.4 g of 4-methoxy-5,6,7,8-tetrahydronaphthol as an off-white solid with a mp of 107-114 !C. An analytical…
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butyllithium and DMF gave only recovered starting material. To a solution of 1.5 g 1,4-dimethoxy-5,6,7,8-tetrahydro-2-naphthaldehyde in 20…
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(I'm posting this for a friend.) This is part 2 of 6 of the second half of PIHKAL: A Chemical Love Story, by Alexander Shulgin and Ann…
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30 2C-G-5; 3,6-DIMETHOXY-4-(2- AMINOETHYL)BENZONORBORNANE SYNTHESIS: To a stirred solution of 25 g 3,6-dihydroxybenzonorbornane (from…
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A solution of LAH (46 mL ofa 1 M solution in THF) was cooled, under He, to 0 !C with an external ice bath. With good stirring there was…
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EXTENSIONS AND COMMENTARY: In the eventual potency assessment of a drug, there must be some consideration of not only the dosage needed,…
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31 2C-G-N; 1,4-DIMETHOXYNAPHTHYL-2- ETHYLAMINE SYNTHESIS: A solution of 17.5 g 1,4-naphthaquinone in 200 mL MeOH was heated to the boiling…
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was followed by the addition of 2.80 g 1,4-dimethoxy-2-(2-nitrovinyl)naphthalene in 40 mL anhydrous THF. There was an immediate loss of…
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EXTENSIONS AND COMMENTARY: There is always a wish in the design of new compounds to find something that is of interesting activity, with an…
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32 2C-H; 2,5- DIMETHOXYPHENETHYLAMINE SYNTHESIS: A solution of 50 g 2,5-dimethoxybenzaldehyde in 100 g nitromethane was treated with 5 g of…
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FOREWORD This book will be different things to different people. There has never been a work like it, and since recent legislative acts in…
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When I lit cigarettes, I could not find my lips well and they were numbed. Matches kept blowing out ina wind that was not strong enough to…
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the future, many possible things as might come froma carbinol group, an amine function, or anything that can stem from a lithium atom.
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33 2C-I; 2,5-DIMETHOXY-4- IODOPHENETHYLAMINE SYNTHESIS: A mixture of 7.4 g phthalic anhydride and 9.05 g of 2,5-dimethoxyphenethylamine…
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DURATION: 6 - 10 h. QUALITATIVE COMMENTS (with 0 mg) I was present at a group meeting, but was only an observer. With zero milligrams of…
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doubt, from a bit of chemical suggestion. The two compounds have structures that are truly analogous, in technical terms. In one, there is…
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34 2C-N; 2,5-DIMETHOXY-4- NITROPHENETHYLAMINE SYNTHESIS: A cooled, stirred solution of 1.0 g 2,5-dimethoxyphenethylamine (see the recipe…
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Final score: body +3, mind +2, barely. EXTENSIONS AND COMMENTARY: A most consistent feature with 2C-N was the fact that in every report,…
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35 2C-O-4; 2,5-DIMETHOXY-4-(i)- PROPOXYPHENETHYLAMINE SYNTHESIS: To a solution of 3.10 g 85% KOH pellets in 30 mL warm MeOH there was added…
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hydride was destroyed by the cautious addition of 8 mL IPA, which was followed by 5 mL 15% NaOH followed, in turn, by sufficient additional…
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4-(n)-butoxy compound 2C-O-19. These are the exact analogues of 2C-T-2, 2C-T-7, and 2C-T-19, resp., and the 2-carbon homologues of MEM,…
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36 2C-P; 2,5-DIMETHOXY-4-(n)- PROPYLPHENETHYLAMINE SYNTHESIS: To a stirred solution of 138 g p-dimethoxybenzene in 400 mL CH2C12 there was…
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began to writhe in his chair, wring his hands, and temporarily lost the ability to speak. I have been in that state. While speaking with…
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homologue remained an oil. Gas chromatographic analysis showed it to be about 90% pure, and it was used as obtained in the nitrostyrene…
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spasm. At first I did not particularly like what this drug was doing to my body, but took a good look at it and decided that I was the…
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PIHKALAnthologyShulgin page 512
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37 CPM; CYCLOPROPYLMESCALINE; 4-CYCLOPROPYLMETHOXY-3,5-DIMETHOXY PHENETHYLAMINE SYNTHESIS: To a solution of 2.8 g homosyringonitrile (see…
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The most remarkable property is the eyes-closed imagery. No, not just imagery but fantasy. It is not completely benign, but it locks into…
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38 2C-SE; 2,5-DIMETHOXY-4- METHYLSELENEOPHENETHYLAMINE SYNTHESIS: A suspension of 5.65 g 1,4-dimethoxybenzene in 100 mL petroleum ether…
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of 0.4 employing CH2C12 as a solvent) when it is once completely dried on the plate, there seems to be some irreversible reaction with the…
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might get to a +++. What doors are opened by the observation that the selenium analog of 2C-T is an active compound? The potency appears to…
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39 2C-T ; 2,5-DIMETHOXY-4- METHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution of 149 g sodium thiosulfate in 300 mL H20 was vigorously stirred.…
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HCl, with 3x50 mL brine and, after drying over anhydrous Na2SO4, the solvent was removed under vacuum. The residue was a solid and, after…
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CHAPTER 7. THE CAPTAIN It was the mid-1960's and the time had come to change my employer. I had worked for the Dole Chemical Company for…
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There are no visuals at all but, rather, a tactile sensitivity, with warm close feelings. This could be very erotic. There is some fantasy…
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had a melting point of 137-138 !C, and the final hydrochloride a melting point of 215-216 !C. The effects were felt very quickly, and there…
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40 2C-T-2; 2,5-DIMETHOXY-4- ETHYLTHIOPHENETHYLAMINE SYNTHESIS: To a solution of 165 g 1,4-dimethoxybenzene in | L of CH2C12, ina well…
PIHKALAnthologyShulgin_page_523
removed under vacuum. The residue was 2,5-dimethoxyphenyl ethyl sulfide which was a pale amber oil, weighed about 10 g and which was…
PIHKALAnthologyShulgin_page_524
DURATION: 6 - 8 h. QUALITATIVE COMMENTS: (with 12 mg) I donUt feel this for fully an hour, but when I do it is quite a weight. It feels…
PIHKALAnthologyShulgin_page_525
2C-T-2 has occasionally been called, simply, T-2. This abbreviated nickname has also been used for T-2 Toxin, a mycotoxin of the…
PIHKALAnthologyShulgin_page_526
41 2C-T-4; 2,5-DIMETHOXY-4-(i)- PROPYLTHIOPHENETHYLAMINE SYNTHESIS: To a solution of 2.5 g of KOH pellets in 40 mL hot EtOH, there was…
PIHKALAnthologyShulgin_page_527
2.72 g of a residue which was distilled at 140-145 !C at 0.2 mn/Hg to give 2.42 g ofa clear white oil. This was dissolved in 25 mL IPA, and…
PIHKALAnthologyShulgin_page_528
I were with other people, this would bring out the worst in me, which can be pretty bad. (with 19 mg) I was caught by the TV. Leonard…
PIHKALAnthologyShulgin_page_529
to thyroxine, an amino acid in the body. The drug 2C-T-4 is neither an explosive nor an amino acid, I am happy to say.
PIHKALAnthologyShulgin_page_53
new and fascinating compounds. But I had very little background for evaluating the biology of their action. Since the scene of that action…
PIHKALAnthologyShulgin_page_530
42 Y-2C-T-4; 2,6-DIMETHOXY-4-(i)- PROPYLTHIOPHENETHYLAMINE) SYNTHESIS: A stirred solution of 8.3 g 3,5- dimethoxy-1-chlorobenzene and 7.2 ¢…
PIHKALAnthologyShulgin_page_531
MeOH, gave fine yellow crystals with a mp of 87.5-89 !C. Anal. (C19H23NO3S) C,H. A solution of 0.8 g…
PIHKALAnthologyShulgin_page_532
something has a common name, and there is a second form (or isomer, or shape, or orientation) that is possible and it doesnUt have a common…
PIHKALAnthologyShulgin_page_533
43 2C-T-7; 2,5-DIMETHOXY-4-(n)- PROPYLTHIOPHENETHYLAMINE SYNTHESIS: To a solution of 3.4 g of KOH pellets in 50 mL hot MeOH, there was…
PIHKALAnthologyShulgin_page_534
2,5-dimethoxy-'-nitro-4-(n)-propylthiostyrene in 50 mL anhydrous THF. There was an immediate loss of color. After a few min further…
PIHKALAnthologyShulgin_page_535
is good and friendly and wonderful as I remember it. I think it is going to take the place of 2C-T-2 in my heart. It is a truly good…
PIHKALAnthologyShulgin_page_536
44 2C-T-8; 2,5-DIMETHOXY-4- CYCLOPROPYLMETHYLTHIOPHENETHYI SYNTHESIS: To a solution of 2.8 g of KOH pellets in 25 mL hot MeOH, there was…
PIHKALAnthologyShulgin_page_537
and suspended under 60 mL anhydrous Et2O to provide, after filtering and air drying, 1.13 g of 2,5-…
PIHKALAnthologyShulgin_page_538
Next day, no deficit. Strange. Maybe too much. EXTENSIONS AND COMMENTARY: With 2C-T-8, there are as many negatives as there are positives,…
PIHKALAnthologyShulgin_page_539
45 2C-T-9; 2,5-DIMETHOXY-4-(t)- BUTYLTHIOPHENETHYLAMINE SYNTHESIS: To a well-stirred ice-cold suspension of 2.8 g p-dimethoxybenzene and…
PIHKALAnthologyShulgin_page_54
astronaut-in-outer-space project. The head honcho was a Captain B. Lauder Pinkerton, who was the central hub of many different branches of…
PIHKALAnthologyShulgin_page_540
days, yielding a mixture of yellow crystals and a brown viscous syrup. The solids were separated and recrystallized from 40 mL MeOH to give…
PIHKALAnthologyShulgin_page_541
that there is not the excitement or creativity to connect with, certainly not enough to justify the cost to the body. EXTENSIONS AND…
PIHKALAnthologyShulgin_page_542
46 2C-T-13; 2,5-DIMETHOXY-4-(2- METHOXYETHYLTHIO)PHENETHYLAMIN SYNTHESIS: To a solution of 3.25 g of KOH pellets in 25 mL hot MeOH, there…
PIHKALAnthologyShulgin_page_543
!C sharp. From IPA the product is a burnished gold color with the mp 106-107 !C. Anal. (C13HI7NOSS) C,H. A solution of LAH (40 mL ofa 1 M…
PIHKALAnthologyShulgin_page_544
development, at a half hour when I felt a light head and slight dizziness. There was a solid plus two for a couple of hours. I paid careful…
PIHKALAnthologyShulgin_page_545
47 2C-T-15; SESQUI; 2,5-DIMETHOXY-4- CYCLOPROPYLTHIOPHENETHYLAMINE SYNTHESIS: To a solution of 3.3 g of KOH pellets in 150 mL hot MeOH,…
PIHKALAnthologyShulgin_page_546
h. The reaction mixture was then poured into H20, the layers separated, and the aqueous phase extracted with CH2C12. The extracts were…
PIHKALAnthologyShulgin_page_547
filtration, and air dried to give 1.94 g of 2,5-dimethoxy-4-cyclopropylthiophenethylamine hydrochloride (2C- T-15) that had a mp of…
PIHKALAnthologyShulgin_page_548
48 2C-T-17; NIMITZ; 2,5-DIMETHOXY-4-(s)- BUTYLTHIOPHENETHYLAMINE SYNTHESIS: To a solution of 2.6 g of KOH pellets in 50 mL hot MeOH, there…
PIHKALAnthologyShulgin_page_549
dropwise over the course of 2 h. After a few min further stirring, the temperature was brought up to a gentle reflux on the steam bath, and…
PIHKALAnthologyShulgin_page_55
But there was the other world to be seen and explored. This was composed of the many biological research projects in other areas, which had…
PIHKALAnthologyShulgin_page_550
RRS isomer that has carried the psychedelic effects. This probably says something about the nitrogen end, the metabolic end, the RnorthS…
PIHKALAnthologyShulgin_page_551
49 2C-T-21; 2,5-DIMETHOXY-4-(2- FLUOROETHYLTHIO)PHENETHYLAMINE SYNTHESIS: To a solution of 6.9 g of KOH pellets in 100 mL hot MeOH, there…
PIHKALAnthologyShulgin_page_552
amber oil. This was dissolved in 600 mL dilute H2SO4, and washed with 3x50 mL CH2C12 (which removed the light yellow color). The aqueous…
PIHKALAnthologyShulgin_page_553
(with 10 mg) I find I can use it if I set my energy in a direction I really want to go in. Otherwise I can just be stoned and…
PIHKALAnthologyShulgin_page_554
with a melting point of 133-134 !C from either IPA or acetonitrile. The 2,2,2-trifluoroethyl compound, which I have named 2C-T-22, has been…
PIHKALAnthologyShulgin_page_555
50 4-D; 3,5-DIMETHOXY-4- TRIDEUTEROMETHOXY- PHENETHYLAMINE SYNTHESIS: To a solution of 34.0 g homosyringonitrile…
PIHKALAnthologyShulgin_page_556
disappeared. Some visual enhancement, good energy, good communication. It was a very special day for me as I was ina good place pretty much…
PIHKALAnthologyShulgin_page_557
There are also similar reports of the 3-methoxyl group being demethylated in man. Here, studies with 3,5- D…
PIHKALAnthologyShulgin_page_558
51 '-D; 3,4,5-TRIMETHOXY-','- DIDEUTEROPHENETHYLAMINE SYNTHESIS: To a solution of 13.6 g homosyringonitrile (see under ESCALINE for its…
PIHKALAnthologyShulgin_page_559
with 50 mL anhydrous Et2O, removed by filtration, washed first with Et2O/IPA, and then with anhydrous Et2O. After air drying, the final…
PIHKALAnthologyShulgin_page_56
In the months that followed, I maintained contact with some of the other scientists I had come to know at Aerospace, and eventually I…
PIHKALAnthologyShulgin_page_560
strong experience of pleasantness started and continued throughout the experience. I tended to internalize to some extent. Ended on a water…
PIHKALAnthologyShulgin_page_561
Perhaps this is why mescaline requires such a large dosage to be effective in man.
PIHKALAnthologyShulgin_page_562
52 DESOXY; 3,5-DIMETHOXY-4- METHYLPHENETHYLAMINE SYNTHESIS: To a well-stirred solution of 31 g 2,6-dimethoxytoluene in 200 mL CH2C12 there…
PIHKALAnthologyShulgin_page_563
DURATION: 6 - 8 h. QUALITATIVE COMMENTS: (with 40 mg) Initially I felt very chilled, so I lay down under a blanket. Eyes-closed imagery…
PIHKALAnthologyShulgin_page_564
nature of the effects seen. This is the exact meaning of the term Rdesoxy.S RDesS, without, and RoxyS, the oxygen. Since this drug is…
PIHKALAnthologyShulgin_page_565
53 2,4-DMA: 2,4- DIMETHOXYAMPHETAMINE SYNTHESIS: To a solution of 10 g 2,4-dimethoxybenzaldehyde in 50 mL nitroethane there was added 0.5 g…
PIHKALAnthologyShulgin_page_566
under 3,4-DMA. The homologues of 2,4-DMA that were iodinated (or occasionally fluor-inated) were mono- or di- alkylated on the nitrogen,…
PIHKALAnthologyShulgin_page_567
psychedelic, so this research direction never totally caught my fancy. I went on to other things.
PIHKALAnthologyShulgin_page_568
54 2,5-DMA; DMA; 2,5- DIMETHOXYAMPHETAMINE SYNTHESIS: A solution of 10.0 g 2,5-dimethoxybenzaldehyde in 50 mL glacial acetic acid was…
PIHKALAnthologyShulgin_page_569
An intriguing, but little studied, analogue of 2,5-DMA is the compound with methyls in place of the methoxyls. 2,5-Dimethylamphetamine has…
PIHKALAnthologyShulgin_page_57
CHAPTER 8. MEM Just what is a C-natural quarter note? A musician might define it as a little solid-black circle witha vertical arm sticking…
PIHKALAnthologyShulgin_page_570
It has also been prepared by the N,N-dimethylation of 2,5-DMA directly, with formaldehyde and formic acid. This has been called 2,5-DNNA,…
PIHKALAnthologyShulgin_page_571
55 3,4-DMA; 3,4- DIMETHOXYAMPHETAMINE SYNTHESIS: A solution of 33.2 g of veratraldehyde in 15.0 g nitroethane was treated with 0.9 g of n-…
PIHKALAnthologyShulgin_page_572
people who had taken 3,4-DMA. They are written descriptions by the observers who had given 3,4-DMA to psychiatric patients. This is one of…
PIHKALAnthologyShulgin_page_573
acetylhypofluorite and iodinated with chloramine-T-oxidized 122I iodide ion. It was also halogenated with (non-radioactive) bromine and…
PIHKALAnthologyShulgin_page_574
56 DMCPA; 2-(2,5-DIMETHOXY-4- METHYLPHENYL)CYCLOPROPYLAMINE SYNTHESIS: To a solution of 25 g 2,5-dimethoxy-4-methylbenzaldehyde (see the…
PIHKALAnthologyShulgin_page_575
'!C, Anal. (C20H23NO4) C,H.N. A solution of 1.5 g trans-2-(2,5-dimethoxy-4-methylphenyl)carbobenzoxyamidocyclopropane in 120 mL MeOH…
PIHKALAnthologyShulgin_page_576
PIHKALAnthologyShulgin page 576
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37 DME; 3,4-DIMETHOXY-'- HYDROXY PHENETHYLAMINE SYNTHESIS: To a solution of 10.2 g 3,4-dimethoxybenzaldehyde in 10 mL EtOH, cooled to 0 !C,…
PIHKALAnthologyShulgin_page_578
the BOX series, there is a methylenedioxyphenethylamine with a methoxyl group at the '-position, and it is called BOH (q.v.). There, a…
PIHKALAnthologyShulgin_page_579
58 DMMDA; 2,5-DIMETHOXY-3,4- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: Apiole, as the crystalline essential oil…
PIHKALAnthologyShulgin_page_58
locations of atoms rather than adding or taking away specific atoms. The ring component of TMA (called a benzene ring) has five different…
PIHKALAnthologyShulgin_page_580
DURATION: 6 - 8 h. QUALITATIVE COMMENTS: (with 25 mg) The intoxication was there at an hour and a quarter, and I was hit with nausea with…
PIHKALAnthologyShulgin_page_581
DMMDA homologues started with the reduction of the nitrosyrene to the ketone (see under METHYL- MMDA-2 for this preparation), followed by…
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59 DMMDA-?; 2,3-DIMETHOXY-4,5- METHYLENEDIOXYAMPHETAMINE DOSAGE: about 50 mg. DURATION: unknown. QUALITATIVE COMMENTS: (with 50 mg) I am…
PIHKALAnthologyShulgin_page_583
This is part 3 of 6 of the second half of PIHKAL: A Chemical Love Story, by Alexander Shulgin and Ann Shulgin. Please forgive any typos or…
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60 DMPEA; 3,4- DIMETHOXYPHENETHYLAMINE SYNTHESIS: A solution of 33 g 3,4-dimethoxybenzaldehyde in 140 mL acetic acid was treated with 23 mL…
PIHKALAnthologyShulgin_page_585
dopamine because it is an amine that comes from an amino acid that is 3,4-dihydroxyphenylalanine and this, in German, is…
PIHKALAnthologyShulgin_page_586
spot in the chromatographic analysis of urines of schizophrenic patients. This had nothing to do with DMPEA. I was working closely with a…
PIHKALAnthologyShulgin_page_587
61 DOAM; 2,5-DIMETHOXY-4-(n)- AMYLAMPHETAMINE SYNTHESIS: A solution of 110 g p-dimethoxybenzene and 102 g valeric acid in 168 g…
PIHKALAnthologyShulgin_page_588
90% pure 2,5-dimethoxy-(n)-amylbenzene. A mixture of 36.3 g POCI3 and 40.9 g N-methylformanilide was allowed to incubate for 0.5 h. To this…
PIHKALAnthologyShulgin_page_589
DURATION: unknown. QUALITATIVE COMMENTS: (with 10 mg) There was a clear threshold that in no way interfered with my day's activities. I was…
PIHKALAnthologyShulgin_page_59
About 15 minutes later, I was clearly intoxicated (in the ethanol sense) but there were absolutely no apprehensions. There was a very…
PIHKALAnthologyShulgin_page_590
62 DOB; 2,5-DIMETHOXY-4- BROMOAMPHETAMINE SYNTHESIS: To a well-stirred solution of 1.95 g of the free base of 2,5-dimethoxyamphetamine…
PIHKALAnthologyShulgin_page_591
according to a certain book, newly published (just in time, looks like) and he is busy softening the possible disappointment of those who…
PIHKALAnthologyShulgin_page_592
following injection. What was learned? That the LD/50 was somewhere between 100 and 125 mg/Kg for the mouse. And an effective dose in man…
PIHKALAnthologyShulgin_page_593
63 DOBU; 2,5-DIMETHOXY-4-(n)- BUTYLAMPHETAMINE SYNTHESIS: A well stirred suspension of 140 g anhydrous AICI3 in 400 mL CH2Cl2 was treated…
PIHKALAnthologyShulgin_page_594
of equal weight and of identical mp. An analytical sample, from hexane, had the same mp. Anal. (C13H1803) C,H. A solution of 13.2 g…
PIHKALAnthologyShulgin_page_595
evening, and the next day there was a feeling of overall depression. Perhaps that was due to the lack of sleep, but there were no signs of…
PIHKALAnthologyShulgin_page_596
p-dimethoxybenzene) and even it went badly. The desired ketone (2,5-dimethoxyphenyl cyclopropyl ketone) was most difficult to separate from…
PIHKALAnthologyShulgin_page_597
64 DOC; 2,5-DIMETHOXY-4- CHLOROAMPHETAMINE SYNTHESIS: A solution of 6.96 g 2,5-dimethoxyamphetamine hydrochloride (2,5-DMA) in 250 mL H20…
PIHKALAnthologyShulgin_page_598
(with 2.4 mg) Here I am at the sixth hour, and I am still roaring along at a full plus three. I have established that this material is…
PIHKALAnthologyShulgin_page_599
65 DOEF; 2,5-DIMETHOXY-4-(2- FLUOROETHYL)- AMPHETAMINE SYNTHESIS: A well-stirred solution of 0.45 g free base DOB in 2 mL CH2C1l2 was…
PIHKALAnthologyShulgin_page_6
NOTE TO THE READER With this book, PIHKAL, we are making available a body of information concerning the conception, synthesis, definition,…
PIHKALAnthologyShulgin_page_60
At about the one hour point, we were well into the effects, around a plus one and a half. We wandered into the Green Gulch Zen Center just…
PIHKALAnthologyShulgin_page_600
washed with H2O. After drying the organic phase with anhydrous Na2SO4 and removal of the solvent under vacuum, there was obtained 1.34 g…
PIHKALAnthologyShulgin_page_601
my state of mind which is always a good sign. We went to the bedroom at the two and a half hour point, and proceeded to establish that the…
PIHKALAnthologyShulgin_page_602
66 DOET; HECATE; 2,5-DIMETHOXY-4- ETHYLAMPHETAMINE SYNTHESIS: To a solution of 19.7 g 2,5-dimethoxy-4-ethylbenzaldehyde (see the recipe for…
PIHKALAnthologyShulgin_page_603
And an awful lot there with my eyes open. The movement on the concrete floor in the basement when I went downstairs for wood for the…
PIHKALAnthologyShulgin_page_604
authorities who cannot tolerate drugs that distort the senses. The higher levels mentioned here have never been put into the published…
PIHKALAnthologyShulgin_page_605
67 DOI; 2,5-DIMETHOXY-4- IODOAMPHETAMINE SYNTHESIS: A mixture of 14.8 g phthalic anhydride and 19.5 g of 2,5-dimethoxyamphetamine (2,5-…
PIHKALAnthologyShulgin_page_606
DURATION: 16 - 30 h. QUALITATIVE COMMENTS: (with 0.6 mg) There was a nice spacey light-headedness for a few hours, and time seemed to move…
PIHKALAnthologyShulgin_page_607
obligation, but even when trying to sleep later that night there was some residue of imagery; remarkably, it was all in slow motion. The…
PIHKALAnthologyShulgin_page_608
material with the whole body scanner showed most of it accumulating in the gut and liver, with almost none to the brain. For those who find…
PIHKALAnthologyShulgin_page_609
68 DOM; STP; 2,5-DIMETHOXY-4- METHYLAMPHETAMINE SYNTHESIS: To a solution of 54.9 g 2,5-dimethoxy-4-methylbenzaldehyde (see the recipe for…
PIHKALAnthologyShulgin_page_61
That broke the dam. She dissolved in tears and blurted out her secret. Many years before, her mother had suffered from cancer of the…
PIHKALAnthologyShulgin_page_610
2-propanone as white crystals with a mp of 57-59 !C. This ketone has also been described as a pale- yellow oil with a bp of 115-118 !C at…
PIHKALAnthologyShulgin_page_611
There was a shuddering, and a tight jaw, and I am not particularly motivated to talk to anyone. It is more arousing (like amphetamine) than…
PIHKALAnthologyShulgin_page_612
milligram. There is a trace of time slowing and in general a pretty full manic state. There is some mydriasis. Everything had pretty much…
PIHKALAnthologyShulgin_page_613
at the end of the first hour, and the full impact of the drug is not appreciated until some two hours have elapsed. But many of the…
PIHKALAnthologyShulgin_page_614
relationship between these two compounds and the series described elsewhere with the RFS code followed by other numbers, such as F-2 and…
PIHKALAnthologyShulgin_page_615
69 Y-DOM; Z-7; 2,6-DIMETHOXY-4- METHYLAMPHETAMINE SYNTHESIS: To a solution of 2,6-dimethoxy-4-methylbenzaldehyde (mp 92-93 !C from the…
PIHKALAnthologyShulgin_page_616
closed fantasy and shaped imagery was quite remarkable. But some heart arrhythmias and a pretty constant diarrhea made the experience less…
PIHKALAnthologyShulgin_page_617
themselves too publicly, that TMA-2 and TMA-6 were both fully active in the 40 to 50 milligram area. And although not as potent as DOM, the…
PIHKALAnthologyShulgin_page_618
hypotheses that didnUt seem to lead anywhere. Maybe, someday, some single earth-shaking mechanism will emerge to explain everything. But in…
PIHKALAnthologyShulgin_page_619
70 DON; 2,5-DIMETHOXY-4- NITROAMPHETAMINE SYNTHESIS: A solution of 8.4 g 2,5-dimethoxyamphetamine base in 40 mL acetic acid was added…
PIHKALAnthologyShulgin_page_62
CHAPTER 9. DOM DOM appeared on the street in the 1960's under the name of STP and it proved to be for quite a while my hair shirt or, as…
PIHKALAnthologyShulgin_page_620
71 DOPR; 2,5-DIMETHOXY-4-(n)- PROPYLAMPHETAMINE SYNTHESIS: A suspension of 285 g mossy zinc in 285 mL H20 containing 5.7 g mercuric…
PIHKALAnthologyShulgin_page_621
anhydrous HCl gas. The solids that formed were removed by filtration, giving 6.15 g 2,5-dimethoxy-4- (n)-propylamphetamine hydrochloride…
PIHKALAnthologyShulgin_page_622
There had been quite a bit of speculation in the literature that the metabolic attack on DOM was at the 4- position, and this was an…
PIHKALAnthologyShulgin_page_623
72 E; ESCALINE; 3,5-DIMETHOXY-4- ETHOXY PHENETHYLAMINE SYNTHESIS: To a solution of 72.3 g 2,6-dimethoxyphenol in 400 mL MeOH, there was…
PIHKALAnthologyShulgin_page_624
heated to reflux in a heating mantle. There was then added a solution of 15 g NaOH in 60 mL H20. The heating and stirring was continued…
PIHKALAnthologyShulgin_page_625
analgesia and an incoordination that I cannot shake. My menstrual flow started a bit ahead of time, but it was light. (with 50 mg) I felt…
PIHKALAnthologyShulgin_page_626
long, and the amphetamine chain is three carbons long. If a drug has been initially developed (and initially named) as an amphetamine…
PIHKALAnthologyShulgin_page_627
73 EEE; 2,4,5-TRIETHOXYAMPHETAMINE SYNTHESIS: A solution of 13.3 g 3,4-diethoxyphenol (see the recipe for MEE for its preparation) in 20 mL…
PIHKALAnthologyShulgin_page_628
and this was extracted with 3x200 mL CH2C12. Removal of the solvent under vacuum produced an amber oil that was dissolved in anhydrous Et2O…
PIHKALAnthologyShulgin_page_629
74 EEM; 2,4-DIETHOXY-5- METHOXYAMPHETAMINE SYNTHESIS: To a solution of 12.3 g 3-ethoxy-4-methoxyphenol (see recipe for MEM for the…
PIHKALAnthologyShulgin_page_63
peaceful contact with the earth and his own inner being.) I completed the nitrostyrene synthesis on July 7th, and finally got back to this…
PIHKALAnthologyShulgin_page_630
course of | h. Refluxing was maintained for 5 h and the reaction mixture was cooled with an external ice bath with the stirring continued.…
PIHKALAnthologyShulgin_page_631
75 EME; 2,5-DIETHOXY-4- METHOXYAMPHETAMINE SYNTHESIS: To a solution of 14.0 g 4-ethoxy-3-methoxyphenol (see the recipe for MME for the…
PIHKALAnthologyShulgin_page_632
under a He atmosphere, there was added 2.8 g 1-(2,5-diethoxy-4-methoxyphenyl)-2-nitropropene by allowing the condensing Et2O to drip into a…
PIHKALAnthologyShulgin_page_633
76 EMM; 4,5-DIMETHOXY-2- ETHOXYAMPHETAMINE SYNTHESIS: A solution of 166 g 3,4-dimethoxybenzaldehyde in 600 mL acetic acid was well stirred,…
PIHKALAnthologyShulgin_page_634
EtOH was treated with 20 g flaked KOH, and heated on the steam bath. The progress of the isomerization was followed by the assay of…
PIHKALAnthologyShulgin_page_635
in early 1963, and the lack of activity of EMM was keenly disappointing. This was a level at which the prototype, TMA-2, was very active,…
PIHKALAnthologyShulgin_page_636
77 ETHYL-J; 2-ETHYLAMINO-1-(3,4- METHYLENEDIOXYPHENYL)BUTANE; N- ETHYL-1-(1,3-BENZODIOXOL-5-YL)-2- BUTANAMINE SYNTHESIS: A stirred solution…
PIHKALAnthologyShulgin_page_637
PIHKALAnthologyShulgin page 637
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78 ETHYL-K; 2-ETHYLAMINO-1-(3,4- METHYLENEDIOXY PHENYL)PENTANE; N- ETHYL-1-(1,3-BENZODIOXOL-5-YL)-2- PENTYLAMINE SYNTHESIS: A solution of…
PIHKALAnthologyShulgin_page_639
79 F-2; 2-M; 6-(2-AMINOPROPYL)-5-METHOXY-2-METHYL-2,3-DIHY DROBENZOFURAN SYNTHESIS: To a solution of 43.2 g KOH pellets in 250 boiling EtOH…
PIHKALAnthologyShulgin_page_64
3.8 milligrams and reported that it showed its maximum effect at the fifth hour, with a peaking from there to the eighth hour, and a…
PIHKALAnthologyShulgin_page_640
To a half-hour pre-incubated mixture of 69 g POCI3 and 60 g N-methylformanilide there was added 29.0 g…
PIHKALAnthologyShulgin_page_641
DOSAGE: greater than 15 mg. DURATION: unknown. EXTENSIONS AND COMMENTARY: This material, which is certainly a mixture of two…
PIHKALAnthologyShulgin_page_642
7-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran. Suddenly here would be a 2,3,5- trisubstituted thing with a ring at the…
PIHKALAnthologyShulgin_page_643
80 F-22; 6-(2-AMINOPROPYL)-2,2-DIMETHYL-5-METHOXY-2,3-DIHY DROBENZOFURAN SYNTHESIS: To a solution of 43.2 g flaked KOH in 250 mL hot EtOH…
PIHKALAnthologyShulgin_page_644
The residual oil (which was shown by GC to contain approximately equal quantities of two isomeric benzaldehydes A and B) was extracted with…
PIHKALAnthologyShulgin_page_645
days. From the first there was obtained 1.4 g of product with a mp of 153-154 !C; from the second, 0.2 g with a mp of 153-154 !C; and from…
PIHKALAnthologyShulgin_page_646
methoxy-2,3,3-trimethyl-2,3-dihydrobenzofuran, remains the stuff of speculation. And a start towards F-23,…
PIHKALAnthologyShulgin_page_647
81 FLEA; N-HYDROXY-N-METHYL-3,4- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: (from 3,4-methylenedioxyphenylacetone) A solution of 2.1 g…
PIHKALAnthologyShulgin_page_648
QUALITATIVE COMMENTS: (with 90 mg) The material tastes terrible, like grapefruit juice that has stayed in the can too long. There was no…
PIHKALAnthologyShulgin_page_649
addition of a hydroxyl group to the amine nitrogen atom of MDMA produces a new drug that is in most of its properties identical to MDMA.…
PIHKALAnthologyShulgin_page_65
CHAPTER 10. PETER MILLE A few years after I had left Dole and taken the initially rather scary step of setting myself up as a scientific…
PIHKALAnthologyShulgin_page_650
82 G-3; 2,5-DIMETHOXY-3,4- (TRIMETHYLENE)AMPHETAMINE; 5-(2- AMINOPROPYL)-4,7-DIMETHOXYINDANE SYNTHESIS: A solution of 3.7 g of…
PIHKALAnthologyShulgin_page_651
for fantasy. (with 18 mg) I amata plus three, but I am not at all sure of why it is a plus three. With my eyes closed, there are puffy…
PIHKALAnthologyShulgin_page_652
83 G-4; 2,5-DIMETHOXY-3,4- (TETRAMETHYLENE)AMPHETAMINE; 6- (2-AMINOPROPYL)-5,8- DIMETHOXYTETRALIN SYNTHESIS: A solution of…
PIHKALAnthologyShulgin_page_653
84 G-5; 3,6-DIMETHOXY-4-(2- AMINOPROPYL)BENZONORBORNANE SYNTHESIS: A solution of 3.70 g 3,6-dimethoxy-4-formylbenzonorbornane (see under…
PIHKALAnthologyShulgin_page_654
(with 20 mg) The transition period, which usually lasts for most compounds for the first hour or two, with this seems to be much longer.…
PIHKALAnthologyShulgin_page_655
85 GANESHA; G; 2,5-DIMETHOXY-3,4- DIMETHYLAMPHETAMINE SYNTHESIS: A solution of 15.4 g 2,5-dimethoxy-3,4-dimethylbenzaldehyde (see under…
PIHKALAnthologyShulgin_page_656
Probably I was simply tired from an inadequate sleep. (with 32 mg) A rapid and full development. Lying down with music, the eyes-closed…
PIHKALAnthologyShulgin_page_657
longer things such as 2C-G-31 and 2C-G-41, which would be the 3-propyl-4-methyl, and the 3-butyl-4- methyl homologues, resp. Unfortunately,…
PIHKALAnthologyShulgin_page_658
86 G-N; 1,4-DIMETHOXYNAPHTHYL-2- ISOPROPYLAMINE SYNTHESIS: To a solution of 3.9 g 1,4-dimethoxy-2-naphthaldehyde (see under 2C-G-N for the…
PIHKALAnthologyShulgin_page_659
of G-N is not only unknown, it has not yet even been sculpted. There can be no more exciting area of research than this, anywhere in the…
PIHKALAnthologyShulgin_page_66
basement of some brownstone residence outside of Stockholm, admiring a bubbling flask filled with LSD. Well, I said, someday maybe,…
PIHKALAnthologyShulgin_page_660
87 HOT-2; 2,5-DIMETHOXY-4-ETHYLTHIO- N-HYDROXYPHENETHYLAMINE SYNTHESIS: A solution of 5.50 g 2,5-dimethoxy-4-ethylthio-'-nitrostyrene (see…
PIHKALAnthologyShulgin_page_661
euphoric. I feel very humbled, that I have a great deal to work out in my life. The next day I find myself very strong and empowered. I see…
PIHKALAnthologyShulgin_page_662
88 HOT-7; 2,5-DIMETHOXY-N-HYDROXY-4- (n)-PROPYLTHIOPHENETHYLAMINE SYNTHESIS: A well-stirred solution of 1.77 g…
PIHKALAnthologyShulgin_page_663
and undecomposed sample of MDOH was actually in hand, and assayed in its own rights, it was found to have a potency that really was the…
PIHKALAnthologyShulgin_page_664
89 HOT-17; 2,5-DIMETHOXY-4-(s)- BUTYLTHIO-N- HYDROXYPHENETHYLAMINE SYNTHESIS: To a well-stirred solution of 6.08 g…
PIHKALAnthologyShulgin_page_665
easy; I was completely content with the day, and would be interested in exploring it under a variety of circumstances. (with 120 mg) This…
PIHKALAnthologyShulgin_page_666
fractionation of these properties. From: sender@mit.edu Newsgroups: sci.med,sci.chem,alt.drugs Subject: PIHKAL: The Chemical Story. File 4…
PIHKALAnthologyShulgin_page_667
90 IDNNA; 2,5-DIMETHOXY-N,N- DIMETHYL-4-IODOAMPHETAMINE SYNTHESIS: To a stirred solution of 0.4 g 2,5-dimethoxy-4-iodoamphetamine…
PIHKALAnthologyShulgin_page_668
But, it is a very close analogue to the extremely potent psychedelic DOI, and it is widely admitted that animal assays are of no use in…
PIHKALAnthologyShulgin_page_669
hydrochloride. An interesting measure of just how different these N,N-dialkylated homologues can be from the psychedelic primary amines,…
PIHKALAnthologyShulgin_page_67
CHAPTER 11. ANDREW One evening, in the late 1950's, I was invited to a musical soiree at an old, comfortable home in the Berkeley Hills. I…
PIHKALAnthologyShulgin_page_670
91 IM; ISOMESCALINE; 2,3,4- TRIMETHOXYPHENETHYLAMINE SYNTHESIS: A solution of 8.0 g 2,3,4-trimethoxybenzaldehyde in 125 mL nitromethane…
PIHKALAnthologyShulgin_page_671
EXTENSIONS AND COMMENTARY: Some fifty years ago this material was given the name Rreciprocal mescalineS in that it was believed to…
PIHKALAnthologyShulgin_page_672
92 IP; ISOPROSCALINE; 3,5-DIMETHOXY-4- (i)-PROPOXY PHENETHYLAMINE SYNTHESIS: A solution of 5.8 g of homosyringonitrile (see under ESCALINE…
PIHKALAnthologyShulgin_page_673
a marvelous ecstatic experience, flowing with and being the energy, body feeling completely free. Noticing how this letting go got one…
PIHKALAnthologyShulgin_page_674
3,4,5-orientation on the benzene ring. However, with IM (isomescaline) there is a rearrangement of substitution pattern on the benzene…
PIHKALAnthologyShulgin_page_675
93 IRIS; 5-ETHOXY-2-METHOXY-4- METHYLAMPHETAMINE SYNTHESIS: To a solution of 9.5 g flaked KOH (10% excess) in 500 mL 95% EtOH there was…
PIHKALAnthologyShulgin_page_676
Evaporation of the solvent under vacuum produced an oil that was dissolved in anhydrous Et2O and saturated with anhydrous HCl gas. There…
PIHKALAnthologyShulgin_page_677
attentive to the phrase, RWe are not yet com-pletely sure of exactly how it works.S What is really meant is, RWe havenUt the slightest idea…
PIHKALAnthologyShulgin_page_678
of Methoxy if 4-located, and other things 3,5.S The end point that soon becomes apparent, down the line, will be to have as many pigeon…
PIHKALAnthologyShulgin_page_679
94 J; BDB; 2-AMINO-1-(3,4- METHYLENEDIOXYPHENYL)BUTANE; 1- (1,3-BENZODIOXOL-5-YL)-2-BUTANAMINE SYNTHESIS: The Grignard reagent of propyl…
PIHKALAnthologyShulgin_page_68
"Sounds good to me," said I. We started sawing away, and about halfway through the first movement, during a brief lull, I glanced at his…
PIHKALAnthologyShulgin_page_680
Anal. (C11H1203) C,H. This intermediate ketone could be prepared by the Wittig reaction between piperonal and the derivative of…
PIHKALAnthologyShulgin_page_681
commented favorably. Perhaps those who have used supplements (in an imitation of the common MDMA procedure) achieved an additional period…
PIHKALAnthologyShulgin_page_682
95 LOPHOPHINE; 3-METHOXY-4,5- METHYLENEDIOXYPHENETHYLAMINE SYNTHESIS: A solution of 50 g myristicinaldehyde…
PIHKALAnthologyShulgin_page_683
QUALITATIVE COMMENTS: (with 150 mg) Between two and five hours, very peaceful and euphoric mood elevation, similar to mescaline, but…
PIHKALAnthologyShulgin_page_684
96 M; MESCALINE; 3,4,5- TRIMETHOXYPHENETHYLAMINE SYNTHESIS: A solution of 20 g 3,4,5-trimethoxybenzaldehyde, 40 mL nitromethane, and 20 mL…
PIHKALAnthologyShulgin_page_685
DURATION: 10-12 h QUALITATIVE COMMENTS: (with 300 mg) I would have liked to, and was expecting to, have an exciting visual day, but I…
PIHKALAnthologyShulgin_page_686
the view and I experienced my first real feeling of persecution and I wanted very much to leave. (with 400 mg) During the initial phase of…
PIHKALAnthologyShulgin_page_687
United States Chemical Warfare group, in their human studies of a number of substituted phenethylamines, used mescaline as the reference…
PIHKALAnthologyShulgin_page_688
milligrams orally failed to produce either physiological or psychological changes. One additional manipulation with some of these…
PIHKALAnthologyShulgin_page_689
97 4-MA; PMA; 4- METHOXYAMPHETAMINE SYNTHESIS: A solution of 27.2 g anisaldehyde and 18.0 g nitroethane in 300 mL benzene was treated with…
PIHKALAnthologyShulgin_page_69
"Why would you invite a known felon to your home?" "Who?" "Mr. Stanley," said the lawyer. "Mr. Stanley has never been to my home," I said…
PIHKALAnthologyShulgin_page_690
(with 70 mg) It hit quite suddenly. I had a feeling of druggedness, almost an alcohol-like intoxication, and I never was really high in the…
PIHKALAnthologyShulgin_page_691
98 MADAM-6; 2,N-DIMETHYL-4,5- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: A mixture of 102 g POCI3 and 115 g N-methylformanilide was allowed to…
PIHKALAnthologyShulgin_page_692
poured into 2 L dilute H2S04 (caution, HCN evolved). This was washed with 3x75 mL CH2C12, made basic with 25% NaOH, and the resulting…
PIHKALAnthologyShulgin_page_693
Anyway, MADAM-6 is not active. And the equally intriguing positional isomer, the easily made MADAM-?, will certainly contribute to these…
PIHKALAnthologyShulgin_page_694
99 MAL; METHALLYLESCALINE; 3,5-DIMETHOXY-4-METHALLYLOXYPHENETHYLAMINE) SYNTHESIS: To a solution of 5.8 g of homosyringonitrile (see under…
PIHKALAnthologyShulgin_page_695
not choose to repeat the experiment. (with 45 mg) I am basically favorably impressed. I believe the initial discomfort would be alleviated…
PIHKALAnthologyShulgin_page_696
Fortunately, MAL did not live up to its name (at least for me), although some of the experimental subjects might disagree! One additional…
PIHKALAnthologyShulgin_page_697
100 MDA; 3,4- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: (from piperonal) To a solution of 15.0 g piperonal in 80 mL glacial acetic acid there…
PIHKALAnthologyShulgin_page_698
then extracted with 3x100 mL CH2C12, these extracts combined, and the solvent removed under vacuum to provide 3.8 g of a red-colored…
PIHKALAnthologyShulgin_page_699
later in the experiment, and it tasted good, but there was absolutely no appetite. None at all. (with 60 mg of the RRS isomer) There was a…
PIHKALAnthologyShulgin_page_7
SEARCH FOR A TITLE In trying to settle ona title for his book, a writer aims for something which both author and reader will find…
PIHKALAnthologyShulgin_page_70
"No," replied a suddenly interested Honorable Claude Pepper, "I've often wondered about that." The audience sensed something dramatic about…
PIHKALAnthologyShulgin_page_700
of the psychedelics to be a fertile field for searching. The giving of relatively unexplored drugs ina cavalier manner to knowing and…
PIHKALAnthologyShulgin_page_701
at-ease, possible time distortion, and a feeling of being keenly aware of one's surroundings. The duration of effects was 4 hrs. The…
PIHKALAnthologyShulgin_page_702
101 MDAL; N-ALLYL-MDA,; 3,4- METHYLENEDIOXY-N- ALLYLAMPHETAMINE SYNTHESIS: A total of about 20 mL allylamine was introduced under the…
PIHKALAnthologyShulgin_page_703
102 MDBU; N-BUTYL-MDA,; 3,4- METHYLENEDIOXY-N- BUTYLAMPHETAMINE SYNTHESIS: A total of 30 mL butylamine was introduced under the surface of…
PIHKALAnthologyShulgin_page_704
6, after distillation at 70-75 !C at 0.3 mmn/Hg, produced N-butylamphetamine hydrochloride (23.4 g from 16.3 g P-2-P). And, in the same…
PIHKALAnthologyShulgin_page_705
103 MDBZ; N-BENZYL-MDA; 3,4- METHYLENEDIOXY-N- BENZYLAMPHETAMINE SYNTHESIS: To a suspension of 18.6 g benzylamine hydrochloride in 50 mL…
PIHKALAnthologyShulgin_page_706
Here too, there appears to be little if any activity in the N-benzyl analogue of MDA. A number of other variations had been synthesized,…
PIHKALAnthologyShulgin_page_707
mmn/Hg) there was eventually gotten a fine hydrochloride salt (MDOC) as white crystals with a mp of 206-208 !C. Anal. (C18H30CINO2) N. As…
PIHKALAnthologyShulgin_page_708
104 MDCPM; CYCLOPROPYLMETHYL- MDA; 3,4-METHYLENEDIOXY-N-CYCLOPROP YLMETHYLAMPHETAMINE SYNTHESIS: A solution of 9.4 g cyclopropylmethylamine…
PIHKALAnthologyShulgin_page_709
105 MDDM; N,N-DIMETHYL-MDA; 3,4-METHYLENEDIOXY-N,N-DIMETHYLAMPHETAMINE SYNTHESIS: To a well stirred solution of 9.7 g dimethylamine…
PIHKALAnthologyShulgin_page_71
numbers, and agreed to meet again in the near future. I had no way of guessing that he would become one of my closest and most valued…
PIHKALAnthologyShulgin_page_710
EXTENSIONS AND COMMENTARY: I cannot attest for the actual drug that had been used in the two larger-dose reports above. These are from an…
PIHKALAnthologyShulgin_page_711
106 MDE; MDEA; EVE; N-ETHYL-MDA; 3,4-METHYLENEDIOXY-N-ETHY_LAMPHETAMINE SYNTHESIS: (from MDA) To a solution of 3.6 g of the free base of…
PIHKALAnthologyShulgin_page_712
!C at 0.5 mm/Hg, producing 40.3 g of an off-white oil. This was dissolved in 600 mL IPA, neutralized with about 20 mL of concentrated HCI…
PIHKALAnthologyShulgin_page_713
felt quite intoxicated and tranquilized. (with 200 mg) Very stoned. There was some nausea in the beginning of the experience. As it…
PIHKALAnthologyShulgin_page_714
has been used for it as well, but there has been no apparent reason advanced for this. And a final note on nomenclature. An old literature…
PIHKALAnthologyShulgin_page_715
107 MDHOET; HYDROXYETHYL-MDA; 3,4-METHYLENEDIOXY-N-(2-HYDROXYETHYL)AMPHETAMINE SYNTHESIS: To a well stirred solution of 25 g ethanolamine…
PIHKALAnthologyShulgin_page_716
108 MDIP; N-ISOPROPYL-MDA; (3,4-METHYLENEDIOXY-N-ISOPROPYLAMPHETAMINE) SYNTHESIS: To a well stirred and cooled solution of 14.75 g…
PIHKALAnthologyShulgin_page_717
MDMA was taken. The effects of the MDMA were noted at the 33 minute point, and an honest plus one was achieved at one hour. At this point a…
PIHKALAnthologyShulgin_page_718
109 MDMA; MDM; ADAM; ECSTASY; 3,4- METHYLENEDIOXY-N- METHYLAMPHETAMINE SYNTHESIS: (from MDA) A solution of 6.55 g of…
PIHKALAnthologyShulgin_page_719
All volatile components were removed under vacuum which yielded some 60 g of a very deep red residue. This was dissolved in 60 mL of MeOH,…
PIHKALAnthologyShulgin_page_72
CHAPTER 12. MDMA It was in 1967, Y.F.C (Year of the Flower Children), that I attended a conference on Ethnopharmacology that was held in…
PIHKALAnthologyShulgin_page_720
sufficient HCl added to make the phase distinctly acidic. This was then washed with 3x75 mL CH2C12, made basic with 25% NaOH, and extracted…
PIHKALAnthologyShulgin_page_721
hours, I could see the whole mental state disintegrating and my pleasant feelings were coming back. But so was my plain, ornery tiredness.…
PIHKALAnthologyShulgin_page_722
for about an additional hour, with only a modest exacerbation of the usual physical side-effects, namely, teeth clenching and eye…
PIHKALAnthologyShulgin_page_723
totally weird stuff without any apparent relationship to psychedelics, psychoactives or psychotropics whatsoever. I know of one chemical…
PIHKALAnthologyShulgin_page_724
110 MDMC; EDMA; 3,4-ETHYLENEDIOXY- N-METHYLAMPHETAMINE SYNTHESIS: To a solution of 27.6 g protocatechualdehyde (3,4-dihydroxybenzaldehyde)…
PIHKALAnthologyShulgin_page_725
chloride in 70 mL water. After standing at room temperature for 30 min, the H2O was drained away, and the amalgamated aluminum washed twice…
PIHKALAnthologyShulgin_page_726
level might be, or how consistent that level might be between different people, or for that matter what the responses are that might be…
PIHKALAnthologyShulgin_page_727
111 MDMEO; N-METHOXY-MDA; 3,4- METHYLENEDIOXY-N- METHYOXYAMPHETAMINE SYNTHESIS: To a solution of 20.9 g methoxyamine hydrochloride in 75 mL…
PIHKALAnthologyShulgin_page_728
sufficient all by itself.
PIHKALAnthologyShulgin_page_729
112 MDMEOET; N-METHOXYETHYL-MDA; 3,4-METHYLENEDIOXY-N-(2-METHOXYETHYL)AMPHETAMINE SYNTHESIS: A crude solution of methoxyethylamine…
PIHKALAnthologyShulgin_page_73
With his death, in 1972, Danny's protege. Earl Usdin/ carried forward many of the projects that they had worked on together, and remarkably…
PIHKALAnthologyShulgin_page_730
113 MDMP; a,a,N-TRIMETHYL-3,4- METHYLENEDIOXY-PHENETHYLAMINE; METHYLENEDIOXYMEPHENTERMINE SYNTHESIS: To a well stirred solution of 1.64 g…
PIHKALAnthologyShulgin_page_731
114 MDOH; N-HYDROXY-MDA; 3,4- METHYLENEDIOXY-N- HYDROXYAMPHETAMINE SYNTHESIS: To a well stirred solution of 14.8 g hydroxylamine…
PIHKALAnthologyShulgin_page_732
phenomena. The experience continued ina rich, meaningful way. There was a marvelous inner glow, the warmth from all the other participants…
PIHKALAnthologyShulgin_page_733
115 MDPEA; 3,4- METHYLENEDIOXYPHENETHYLAMINE; HOMOPIPERONYLAMINE SYNTHESIS: A suspension of 4.0 g LAH in 300 mL anhydrous Et2O was stirred…
PIHKALAnthologyShulgin_page_734
The number for MDA itself was EA-1298. The beta-hydroxy analogue of MDPEA is the ethanolamine MDE, standing for methylenedioxyethanolamine.…
PIHKALAnthologyShulgin_page_735
116 MDPH; a,a-DIMETHYL-3,4- METHYLENEDIOXY- PHENETHYLAMINE; 3,4-METHYLENEDIOXYPHENTERMINE SYNTHESIS: To 150 mL of THF, under an atmosphere…
PIHKALAnthologyShulgin_page_736
This carbamate was reduced to the primary amine (below) or to the methylamine (see under MDMP). A solution of 3.27 g of…
PIHKALAnthologyShulgin_page_737
are statements of relationships and, if the premises are true, there are only certain conclusions that may logically follow. For example:…
PIHKALAnthologyShulgin_page_738
Therefore, some ring-unsubstituted 1,1-dimethylphenylethyl amines when given a methylenedioxy group are MDMA-like. The conclusion is the…
PIHKALAnthologyShulgin_page_739
117 MDPL; N-PROPARGYL-MDA,; N- PROPYNYL-MDA; 3,4-METHYLENEDIOXY- N-PROPARGYLAMPHETAMINE) SYNTHESIS: A solution of 10.5 ¢g propargylamine…
PIHKALAnthologyShulgin_page_74
discovery of medicines in plants. There was Steven Szara of DMT fame, and Andy Weil, Gordon Wasson, Nathan Kline, Harry Isbell, Danny…
PIHKALAnthologyShulgin_page_740
118 MDPR; N-PROPYL-MDA; 3,4- METHYLENEDIOXY-N- PROPYLAMPHETAMINE SYNTHESIS: A total of 20 mL concentrated HCl was added beneath the surface…
PIHKALAnthologyShulgin_page_741
QUALITATIVE COMMENTS: (with 160 mg followed at 2 h by 60 5gs LSD) RThe visual phenomena were extraordinary. We were at the beach just south…
PIHKALAnthologyShulgin_page_742
and the generated state was overwhelmingly erotic and out of body. There can be no way of analytically organizing such a gemisch of…
PIHKALAnthologyShulgin_page_743
119 ME; METAESCALINE; 3,4- DIMETHOXY-5- ETHOXYPHENETHYLAMINE SYNTHESIS: To a vigorously stirred suspension of 18.6 g of 5-bromobourbonal in…
PIHKALAnthologyShulgin_page_744
reacidified with HCl, and reextracted with 2x100 mL CH2CI2. After pooling, the solvent was removed under vacuum to yield an oily residue.…
PIHKALAnthologyShulgin_page_745
added slowly with continuous stirring. The white crystalline 3,4-dimethoxy-5-ethoxyphenethylamine hydrochloride (ME) was isolated by…
PIHKALAnthologyShulgin_page_746
second hour, I seem to be stuck at a ++. Take another 100 milligrams at 3:45 PM. Still tastes awful. Feel a small head-rush fifteen minutes…
PIHKALAnthologyShulgin_page_747
action which might lead to the tragic ruination ofa life. It should also be noted that any person anywhere who experiments on himself, or…
PIHKALAnthologyShulgin_page_748
120 MEDA; 3-METHOXY-4,5- ETHYLENEDIOXYAMPHETAMINE SYNTHESIS: To a solution of 50 g 3,4-dihydroxy-5-methoxybenzaldehyde in 100 mL distilled…
PIHKALAnthologyShulgin_page_749
under 50 mL of slightly moist acetone, providing 4.92 g of 3-methoxy-4,5-ethylenedioxyamphetamine hydrochloride monohydrate (MEDA) as white…
PIHKALAnthologyShulgin_page_75
and had been adequately entertained. One of my more devoted students was a sweet youngster, a guitar player, who had the world's most…
PIHKALAnthologyShulgin_page_750
121 MEE; 4,5-DIETHOXY-2- METHOXYAMPHETAMINE SYNTHESIS: To a solution of 166 g bourbonal in 1 L MeOH there was added a solution of 66 g KOH…
PIHKALAnthologyShulgin_page_751
pellets dissolved in 200 mL hot MeOH. There was then added 21.4 g methyl iodide, and the mixture was held at reflux for 2 h on the steam…
PIHKALAnthologyShulgin_page_752
pH was >9, and this was extracted with 3x200 mL CH2C12. Removal of the solvent under vacuum produced an off-white oil that was dissolved in…
PIHKALAnthologyShulgin_page_753
122 MEM; 2,5-DIMETHOXY-4- ETHOXYAMPHETAMINE SYNTHESIS: A solution of 83 g bourbonal (also called ethyl vanillin, or vanillal, or simply…
PIHKALAnthologyShulgin_page_754
distilled as a clear oil at 180-190 !C at 0.8 mn/Hg. This product, 45.1 g, gave a fine NMR spectrum, and in dilute CCl4 showed a single OH…
PIHKALAnthologyShulgin_page_755
with an external ice bath. The excess hydride was destroyed by the cautious addition of 300 mL of 1.5 N H2S04. When the aqueous and Et2O…
PIHKALAnthologyShulgin_page_756
There was a persistent queasiness that never left me, and it contrasted oddly with a good feeling of outward articulation and lucidity…
PIHKALAnthologyShulgin_page_757
MEM seems to have had more trials using this combination than many of the other psychedelic drugs.
PIHKALAnthologyShulgin_page_758
123 MEPEA; 3-METHOXY-4- ETHOXY PHENETHYLAMINE SYNTHESIS: A solution of 10.0 g 3-methoxy-4-ethoxybenzaldehyde in 150 mL nitromethane was…
PIHKALAnthologyShulgin_page_759
And there is an interesting story attached. I got a call out of absolutely nowhere, from a Stanislov Wistupkin, that he had discovered a…
PIHKALAnthologyShulgin_page_76
state with alcohol, there was a daily change of personality, revealing towards the end of the evening an outspoken, largely anti-everything…
PIHKALAnthologyShulgin_page_760
124 META-DOB; 5-BROMO-2,4- DIMETHOXYAMPHETAMINE SYNTHESIS: The reaction of 2,4-dimethoxyamphetamine (2,4-DMA) with elemental bromine…
PIHKALAnthologyShulgin_page_761
is all discussed in the 3,4-DMA recipe.
PIHKALAnthologyShulgin_page_762
125 META-DOT; 2,4-DIMETHOXY-S- METHYLTHIOAMPHETAMINE SYNTHESIS: To 27 g 1,3-dimethoxybenzene that was being well stirred, there was added,…
PIHKALAnthologyShulgin_page_763
The other melted at 124.5-125.5 !C and had major fingerprint peaks at 694, 731, 839 and 897 cm-1. Anal. (C10H1203S) C,H. A solution of 8.2…
PIHKALAnthologyShulgin_page_764
active as DOM, but both ORTHO-DOT and the compound described here, META-DOT, were down by factors of 50x and 30x respectively. These animal…
PIHKALAnthologyShulgin_page_765
126 METHYL-DMA; DMMA; 2,5- DIMETHOXY-N-METHYLAMPHETAMINE SYNTHESIS: To a stirred solution of 28.6 g methylamine hydrochloride in 120 mL…
PIHKALAnthologyShulgin_page_766
There is an interesting, and potentially informative, convergence of the metabolite of one drug with the structure of another. Under 4-MA,…
PIHKALAnthologyShulgin_page_767
127 METHYL-DOB; 4-BROMO-2,5- DIMETHOXY-N-METHYLAMPHETAMINE SYNTHESIS: To a solution of 6.0 g of the free base of…
PIHKALAnthologyShulgin_page_768
EXTENSIONS AND COMMENTARY: The mention above, of the 10 milligrams of METHYL-DOB followed by 5 milligrams of psilocybin, leads to some…
PIHKALAnthologyShulgin_page_769
128 METHYL-J; MBDB; EDEN; 2-METHYLAMINO-1-(3,4-METHYLENEDIOXYPHENYL)BUTANE; N-METHYL-1-(1,3- BENZODIOXOL-5-YL)-2-BUTANAMINE SYNTHESIS: A…
PIHKALAnthologyShulgin_page_77
That was it. She plunged into the MDMA state, and started running down the hill, calling out that it was all right to be alive. All the…
PIHKALAnthologyShulgin_page_770
(with 210 mg and a 50 mg supplement) RTasted perfectly rotten. Suspect I was getting some type of alert in 5 minutes (I often get one…
PIHKALAnthologyShulgin_page_771
was familiarly called RJacobamineS in recognition of a famous chemist who had set the synthetic wheels in motion. It is quite obvious, that…
PIHKALAnthologyShulgin_page_772
129 METHYL-K; 2-METHYLAMINO-1-(3,4- METHYLENEDIOXY PHENYL)PENTANE; N- METHYL-1-(1,3-BENZODIOXOL-S-YL)-2- PENTYLAMINE SYNTHESIS: The…
PIHKALAnthologyShulgin_page_773
H20. The mixture was heated briefly until there were clear signs of active amalgamation, such as fine bubbling for the aluminum surfaces…
PIHKALAnthologyShulgin_page_774
amino- | -(3,4-methylenedioxyphenyl)hexane hydrochloride (L) as a white crystalline product with a mp of 157-158 '!C, Anal. (C13H20CINO2)…
PIHKALAnthologyShulgin_page_775
130 METHYL-MA; PMMA; DOONE; 4-MMA; 4-METHOXY-N-METHYLAMPHETAMINE SYNTHESIS: A solution of 20 g methylamine hydrochloride in 150 mL hot MeOH…
PIHKALAnthologyShulgin_page_776
RVoila,S said one of them, with a molecular model in his hands, RLegal as sea salt.S And what is MDMA with one oxygen atom removed? It is…
PIHKALAnthologyShulgin_page_777
131 METHYL-MMDA-2; 2-METHOXY-N- METHYL-4,5- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: A suspension of 17.4 g electrolytic elemental iron in 100…
PIHKALAnthologyShulgin_page_778
discussed here, again of reduced activity. The highest dose yet reported was 70 milligrams, and there is no way of estimating what miight…
PIHKALAnthologyShulgin_page_779
132 MMDA; 3-METHOXY-4,5- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: (from protocatechualdehyde) A solution of 18 g commercial…
PIHKALAnthologyShulgin_page_78
people. There is another part of the MDMA story which should be told, and it concerns a kind, elderly psychologist who was everyone's idea…
PIHKALAnthologyShulgin_page_780
butyllithium in hexane (the fine solids dissolved) followed by 4.0 mL of tributyl borate. After returning to room temperature, the reaction…
PIHKALAnthologyShulgin_page_781
!C and filtered through a coarse sintered glass funnel to remove some insoluble fines. The clear filtrate was brought up almost to a boil,…
PIHKALAnthologyShulgin_page_782
A mixture of 50 g 1-(3-methoxy-4,5-methylenedioxyphenyl)-2-nitropropene and 26 g racemic a-methylbenzylamine was heated on the steam bath.…
PIHKALAnthologyShulgin_page_783
in visual scene (except for some greenish tinges in faces) but upon closing eyes hallucinations appear to be quite real in 3-D, like…
PIHKALAnthologyShulgin_page_784
133 MMDA-2; 2-METHOXY-4,5- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: A solution of 11.5 g pellet KOH (85%) in 75 mL EtOH was treated with 25 g…
PIHKALAnthologyShulgin_page_785
The addition required 2 h and the reflux was maintained for 36 h. The reaction mixture was then cooled in an ice bath and there was added,…
PIHKALAnthologyShulgin_page_786
EXTENSIONS AND COMMENTARY: A comparison of this material to MDA was often made by subjects who were familiar with both. But it is hard to…
PIHKALAnthologyShulgin_page_787
134 MMDA-3a; 2-METHOXY-3,4- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: To a solution of 100 g of 2,3-dihydroxyanisole in 1 L dry acetone there…
PIHKALAnthologyShulgin_page_788
from EtOH raised this mp to 109.5-110.5 IC, A suspension of 2.2 g LAH in 300 mL anhydrous Et2O under an inert atmosphere was brought to a…
PIHKALAnthologyShulgin_page_789
of sticking these two groupings on the aromatic ring. The numbers 1-6 had already been assigned to the six ways of sticking three methoxyl…
PIHKALAnthologyShulgin_page_79
introducing MDMA to other therapists and teaching them how to use it in their therapy. They all had to begin, of course, by learning its…
PIHKALAnthologyShulgin_page_790
135 MMDA-3b; 4-METHOXY-2,3- METHYLENEDIOXYAMPHETAMINE SYNTHESIS: A solution of 7.0 g of 98% pure (by GC)…
PIHKALAnthologyShulgin_page_791
the 3a, but no one can say by how much. The literature statement is that it is threefold less, but that was based on the relative responses…
PIHKALAnthologyShulgin_page_792
136 MME; 2,4-DIMETHOXY-5- ETHOXYAMPHETAMINE SYNTHESIS: A solution was made of 166 g ethylvanillin (4-ethoxy-3-methoxybenzaldehyde) in 600…
PIHKALAnthologyShulgin_page_793
yellow crystals began to form. After standing overnight, these were removed by filtration and sucked as dry as possible, yielding 16 g of a…
PIHKALAnthologyShulgin_page_794
just under a ++, with the earmarks of a possibly interesting collection of effects, were it just a bit more intense. I had unexpected…
PIHKALAnthologyShulgin_page_795
MEM. The third possible ethoxy compound is EMM and, as will be found elsewhere in this book, it is even less active. Thus it is MEM, only,…
PIHKALAnthologyShulgin_page_796
137 MP; METAPROSCALINE; 3,4- DIMETHOXY-5-(n)- PROPOXYPHENETHYLAMINE SYNTHESIS: There was mixed 96 g of 5-bromovanillin and 90 mL 25% NaOH.…
PIHKALAnthologyShulgin_page_797
under vacuum to yield a brown viscous oil as a residue. This was distilled at 105-120 !C at 0.2 mm/Hg to yield 8.8 g of…
PIHKALAnthologyShulgin_page_798
1.3 g 3,4-dimethoxy-5-(n)-propoxyphenethylamine hydrochloride (MP) with a mp of 170-171 !C. Anal. (C13H22CINO3) C,H. DOSAGE: greater than…
PIHKALAnthologyShulgin_page_799
138 MPM; 2,5-DIMETHOXY-4-(n)- PROPOXYAMPHETAMINE SYNTHESIS: To a solution of 68 g 2,5-dimethoxybenzaldehyde in 250 mL glacial acetic acid…
PIHKALAnthologyShulgin_page_8
Most of the names in this story have been changed to protect personal privacy and to allow us freedom in the telling of our tale. Certain…
PIHKALAnthologyShulgin_page_80
So, at 2:00 PM, I had taken 100 milligrams.of MDOH, and had recorded a typical chronology and response to it. Later in the afternoon, as…
PIHKALAnthologyShulgin_page_800
encouraged the separation of crystals which were removed, and had a mp of 150-152 !C. Recrystallization from toluene gave gold-colored…
PIHKALAnthologyShulgin_page_801
For the preparation of MIPM, the above phenol, 2,5-dimethoxyphenol was isopropylated with isopropyl bromide in methanolic KOH giving…
PIHKALAnthologyShulgin_page_802
139 ORTHO-DOT; 4,5-DIMETHOXY-2- METHYLTHIOAMPHETAMINE SYNTHESIS: To 26.4 g veratrol that was being magnetically stirred without any…
PIHKALAnthologyShulgin_page_803
Anal. (C10H1203S) C,H. A solution of 2.0 g 4,5-dimethoxy-2-(methylthio)benzaldehyde in 8 mL nitroethane was treated with 0.45 g anhydrous…
PIHKALAnthologyShulgin_page_804
140 P; PROSCALINE; 3,5-DIMETHOXY-4-(n)- PROPOXYPHENETHYLAMINE SYNTHESIS: A solution of 5.8 g of homosyringonitrile (see under E for its…
PIHKALAnthologyShulgin_page_805
(with 40 mg) For me there was a deep feeling of peace and contentment. The euphoria grows in intensity for several hours and remains for…
PIHKALAnthologyShulgin_page_806
141 PE; PHENESCALINE; 3,5-DIMETHOXY- 4-PHENETHYLOXYPHENETHYLAMINE SYNTHESIS: To a solution of 5.8 g homosyringonitrile (see under E for its…
PIHKALAnthologyShulgin_page_807
psychological effects. A similar chain on the 4-position, but with one less carbon atom, deserves special comment. Rather than a…
PIHKALAnthologyShulgin_page_808
142 PEA; PHENETHYLAMINE SYNTHESIS: This compound has been made industrially by a number of routes, the motant being the reduction of benzyl…
PIHKALAnthologyShulgin_page_809
comment, phenylacetic acid is a major precursor in the illicit synthesis of amphetamine and methamphetamine. Phenethylamine is…
PIHKALAnthologyShulgin_page_81
It was now 8:38 PM and I knew intellectually that only twenty-five minutes had elapsed since I felt the first effects. Twenty-five days…
PIHKALAnthologyShulgin_page_810
might be found in and around compounds such as (1) the MDMA analogue, N-(3,4- methylenedioxybenzyl)piperazine (or its N-methyl-counterpart…
PIHKALAnthologyShulgin_page_811
And there is one more obvious remaining methylation pattern. What about phenethylamine or amphetamine compounds with two methyl groups on…
PIHKALAnthologyShulgin_page_812
143 PROPYNYL; 3,5-DIMETHOXY-4-(2- PROPYNYLOXY)PHENETHYLAMINE SYNTHESIS: To a solution of 5.8 g homosyringonitrile (see under E for its…
PIHKALAnthologyShulgin_page_813
spiritual or adventurous sense. But also I am somewhat physically fuzzy. I feel that if I were in public my behavior would be such that…
PIHKALAnthologyShulgin_page_814
144 SB; SYMBESCALINE; 3,5-DIETHOXY-4- METHOXY PHENETHYLAMINE SYNTHESIS: A solution of 15 g 1,3-diethoxybenzene and 15 mL of N,N,NU,NU-…
PIHKALAnthologyShulgin_page_815
3,5-diethoxy-4-methoxyphenylacetonitrile as a solid. This weighed 1.3 g and had a mp of 58-59 !C. Anal. (C13H17NO3) C,H. To 30 mL ofa | M…
PIHKALAnthologyShulgin_page_816
than that of mescaline. However you phrase it, someone will misinterpret it.
PIHKALAnthologyShulgin_page_817
145 TA; 2,3,4,5- TETRAMETHOXYAMPHETAMINE SYNTHESIS: To a solution of 50 g 2,3,4-trimethoxybenzaldehyde in 157 mL glacial acetic acid which…
PIHKALAnthologyShulgin_page_818
vacuum to give 13.8 g ofa fluid oil that was surprising pure 2,3,4,5-tetramethoxypropenylbenzene by both GC and NMR analysis. The basic…
PIHKALAnthologyShulgin_page_819
(with 35 mg) I had some gastric upset, but nonetheless there was a distinct intoxication. The next morning I had a foul headache.…
PIHKALAnthologyShulgin_page_82
I put the receiver down on the table and headed in the direction of my office. There will never be a way of reconstructing the myriad…
PIHKALAnthologyShulgin_page_820
146 3-TASB; 3-THIOASYMBESCALINE; 4-ETHOXY-3-ETHYLTHIO-5-METHOXYPHENETHYLAMINE SYNTHESIS: Without any solvent, there was combined 21.7 g of…
PIHKALAnthologyShulgin_page_821
CH2C12, the extracts pooled, washed first with dilute HCl, then with saturated brine, and the solvent removed under vacuum. The residue was…
PIHKALAnthologyShulgin_page_822
To this crude 1-(4-ethoxy-3-ethylthio-5-methoxyphenyl)-2-iodoethane there was added a solution of 20 g potassium phthalimide in 150 mL…
PIHKALAnthologyShulgin_page_823
hour, the mental things drifted away, but the body was still wound up. Sleep was impossible until about 3:00 AM (the 18th hour of the…
PIHKALAnthologyShulgin_page_824
147 4-TASB; 4-THIOASYMBESCALINE; 3-ETHOXY-4-ETHYLTHIO-5-METHOXY PHENETHYLAMINE SYNTHESIS: A solution of 20.5 g…
PIHKALAnthologyShulgin_page_825
fractions The first boiled at 112-125 !C and weighed 3.9 g. It was largely starting bromo compound with a little nitrile, and was…
PIHKALAnthologyShulgin_page_826
(with 100 mg) Music was lovely during the experiment, but pictures were not particularly exciting. I had feelings that my nerve-endings…
PIHKALAnthologyShulgin_page_827
148 5-TASB; 5-THIOASYMBESCALINE; 3,4-DIETHOXY-5-METHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution of 11.5 g…
PIHKALAnthologyShulgin_page_828
to discharge the residual iodine color (about 4 mL was required). The reaction mixture was added to 500 mL water, and sodium hydrosulfite…
PIHKALAnthologyShulgin_page_829
QUALITATIVE COMMENTS: (with 120 mg) Maybe there is something at about hour 5. My talking with innocent people had hints of strangeness. And…
PIHKALAnthologyShulgin_page_83
The name I used for this group of the 4-position sulfur-analogues of TMA-2 was the Aleph family, calling upon the Hebrew alphabet. Using…
PIHKALAnthologyShulgin_page_830
149 TB; 4-THIOBUSCALINE; 3,5- DIMETHOXY-4-(n)- BUTYLTHIOPHENETHYLAMINE SYNTHESIS: A solution was made of 12.1 g…
PIHKALAnthologyShulgin_page_831
4-(n)-butylthio-3,5-dimethoxyphenylacetonitrile, was reduced as such without further purification or analysis. A solution of LAH under N2…
PIHKALAnthologyShulgin_page_832
EXTENSIONS AND COMMENTARY: There is a term Rdose-dependentS in pharmacology. When there is a complex action produced by a drug, then each…
PIHKALAnthologyShulgin_page_833
At the present time, restrictive laws are in force in the United States and it is very difficult for researchers to abide by the…
PIHKALAnthologyShulgin_page_834
150 3-TE; 3-THIOESCALINE; 4-ETHOXY-5-METHOXY-3-METHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution of 10.4 g of…
PIHKALAnthologyShulgin_page_835
additional 10 min. After cooling again, there was added enough IPA to decompose the excess hydride and sufficient 10% NaOH to convert the…
PIHKALAnthologyShulgin_page_836
x 6 Escaline 3-TE Rx20S 40-60 mg = 10-20 mg and one would predict a potency of some 20x that of mescaline, or something in the range of 15…
PIHKALAnthologyShulgin_page_837
151 TE; 4-TE; 4-THIOESCALINE; 3,5- DIMETHOXY-4- ETHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution was made of 45.2 g…
PIHKALAnthologyShulgin_page_838
combined, and extracted with 2x100 mL CH2C12. These extracts were pooled with the original organic phase, and the solvents removed under…
PIHKALAnthologyShulgin_page_839
based on trust. The fear is a return to the past, and is defensive, with reluctance to reexperience past pain. The aftermath of this…
PIHKALAnthologyShulgin_page_84
(2:33) How long does it take to assimilate an act? The act itself, an augenblick [a quick glance], is like a drug effect, in that to…
PIHKALAnthologyShulgin_page_840
152 2-TIM; 2-THIOISOMESCALINE; 3,4- DIMETHOXY-2- METHYLTHIOPHENETHYLAMINE SYNTHESIS: A short foreword to the synthetic portion is needed.…
PIHKALAnthologyShulgin_page_841
determined by GC analysis. If the starting 2,3-dimethoxythioanisole contains appreciable veratrole as a contaminant, then this aldehyde…
PIHKALAnthologyShulgin_page_842
under He and with stirring. There was added, dropwise, 2.8 mL of 100% H2S04, followed by 4.4 g of…
PIHKALAnthologyShulgin_page_843
153 3-TIM; 3-THIOMESCALINE; 2,4- DIMETHOXY-3- METHYLTHIOPHENETHYLAMINE SYNTHESIS: A mixture of 3.1 g POCI3 2.8 g N-methylformanilide was…
PIHKALAnthologyShulgin_page_844
were filtered, washed with Et2O, and air dried. The weight of 2,4-dimethoxy-3-methylthiophenethylamine hydrochloride (3-TIM) was 0.2 g and…
PIHKALAnthologyShulgin_page_845
154 4-TIM; 4-THIOISOMESCALINE; 2,3-DIMETHOXY-4-METHYLTHIOPHENETHYLAMINE SYNTHESIS: The mother liquors from the initial crystallization of…
PIHKALAnthologyShulgin_page_846
C,H,N. DOSAGE: greater than 160 mg. DURATION: unknown. QUALITATIVE COMMENTS: (with 160 mg) Everything seemed normal. Pulse was under 80,…
PIHKALAnthologyShulgin_page_847
155 3-TM; 3-THIOMESCALINE; 3,4- DIMETHOXY-5- METHYLTHIOPHENETHYLAMINE SYNTHESIS: To an ice cold and well stirred solution of 15 g vanillin…
PIHKALAnthologyShulgin_page_848
there was added, dropwise, 0.7 mL of 100% H2S04, followed by a solution of 0.7 g 3,4-dimethoxy-5-methylthio-'-nitrostyrene in 10 mL…
PIHKALAnthologyShulgin_page_849
The spiritual load we see as What others carry. RThis material is not poetic, I should say, does not enhance poetry, prose is much more…
PIHKALAnthologyShulgin_page_85
Next time try tape recorder. With a variable speed as well as a start-stop. No - don't need the stop. True, I could talk faster than I…
PIHKALAnthologyShulgin_page_850
156 TM; 4-TM; 4-THIOMESCALINE; 3,5-DIMETHOXY-4-METHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution of 24.2 g…
PIHKALAnthologyShulgin_page_851
!C, weighed 1.8 g and spontaneously crystallized. It was triturated under cold MeOH and filtered yielding, after air drying, 1.1 g…
PIHKALAnthologyShulgin_page_852
dead dispelled any internal concerns and I ran inside to find the others; they had brought my pillow in. I was alive again, but the entire…
PIHKALAnthologyShulgin_page_853
No new person should ever have to play my wife's old role. I need never again play my old role. And I wonut. (with 30 mg) At 2:20 PM I…
PIHKALAnthologyShulgin_page_854
What is meaning of the phrase, Rsulfur-for-oxygen replacement?S Let me try to explain it for non- chemists. One of the most exciting bits…
PIHKALAnthologyShulgin_page_855
157 TMA: 3,4,5- TRIMETHOXYAMPHETAMINE SYNTHESIS: To a solution of 39.2 g 3,4,5-trimethoxybenzaldehyde in 30 mL warm EtOH there was added…
PIHKALAnthologyShulgin_page_856
NaOH, and the aqueous washes were pooled with the original base phase. The organic phase was stripped of its CH2C12 under vacuum to give an…
PIHKALAnthologyShulgin_page_857
There was an earlier report on TMPEA which is mentioned in the appropriate recipe, but there were few details given. Also there had been…
PIHKALAnthologyShulgin_page_858
oils, or RalmostS amphetamines, can serve as an index for the corresponding real amphetamine counterparts. I had originally called this…
PIHKALAnthologyShulgin_page_859
pain. The propenyl analogue is isoeugenol, with a smell that is subtle but very long lasting, used more in soaps and perfumes than in…
PIHKALAnthologyShulgin_page_86
C; "'--------------------- ." [L apparently censored this concept because it was so personal and private, I simply refused give anyone the…
PIHKALAnthologyShulgin_page_860
remembrance, and pot, well, I guess it is a symbol of a lot of things to a lot of people. Anyway, equal quantities of these three plants…
PIHKALAnthologyShulgin_page_861
treasure chest is TMA-2. (8) The 2,5-dimethoxy-3,4-methylenedioxy pattern. The parent allyl benzene is apiole (with a final ReS) or parsley…
PIHKALAnthologyShulgin_page_862
158 TMA-2; 2,4,5- TRIMETHOXYAMPHETAMINE SYNTHESIS: To a solution of 50 g 2,4,5-trimethoxybenzaldehyde in 175 mL nitroethane there was added…
PIHKALAnthologyShulgin_page_863
woodwork, and the wooden angel hanging on the ceiling was flesh and feathers when I stared at it. Great vision. But by no means…
PIHKALAnthologyShulgin_page_864
The unexpected ten-fold increase of effectiveness uncovered by the simple relocation of a single methoxy group of TMA gave the further…
PIHKALAnthologyShulgin_page_865
A sad note on how things have changed since that time. I recently queried the editors of Nature, about their thoughts concerning a twenty…
PIHKALAnthologyShulgin_page_866
159 TMA-3; 2,3,4- TRIMETHOXYAMPHETAMINE SYNTHESIS: To a solution of 12.4 g 2,3,4-trimethoxybenzaldehyde in 45 mL glacial acetic acid, there…
PIHKALAnthologyShulgin_page_867
MU. If 2 grams had been inactive, it would have been less than 0.1 M.U. But the actual printed form, activity < 2.0 M.U. was accepted by…
PIHKALAnthologyShulgin_page_868
160 TMA-4; 2,3,5- TRIMETHOXYAMPHETAMINE SYNTHESIS: To a solution of 68 g 2,4-dimethoxybenzaldehyde in 250 mL glacial acetic acid that had…
PIHKALAnthologyShulgin_page_869
dimethoxyphenol which resulted from the pyrolytic loss of the allyl group. This mixture was methylated without further purification. To a…
PIHKALAnthologyShulgin_page_87
(3:55) La Boheme, rather surprisingly, is not maudlin but a true friend. And accents in written French express hand movements. The accent…
PIHKALAnthologyShulgin_page_870
atmosphere, there was added a solution of 1.1 g 2-nitro-1-(2,3,5-trimethoxyphenyl)propene in 50 mL anhydrous Et20. The creamy mixture was…
PIHKALAnthologyShulgin_page_871
substitution pattern known to chemists. There just isnUt any simple way to put it together. The 2-carbon phenethylamine…
PIHKALAnthologyShulgin_page_872
161 TMA-5; 2,3,6- TRIMETHOXYAMPHETAMINE SYNTHESIS: A solution of 100 g 1,2,4-trimethoxybenzene in 1 L hexane was cooled to 15 !C and…
PIHKALAnthologyShulgin_page_873
There was then added 6.5 g tetranitromethane over the course of | min, the stirring was continued for an additional 2 min, and then the…
PIHKALAnthologyShulgin_page_874
The first question is addressed by taking a number of known psychedelic drugs, and searching for some animal responses that are common to…
PIHKALAnthologyShulgin_page_875
162 TMA-6; 2,4,6- TRIMETHOXYAMPHETAMINE SYNTHESIS: To a solution of 100 g phloroglucinol dihydrate in 320 mL MeOH there was added 55 mL of…
PIHKALAnthologyShulgin_page_876
THF drip through a Soxhlet thimble containing the nitrostyrene with direct addition to the reaction mixture. The solubility was extremely…
PIHKALAnthologyShulgin_page_877
stomach queasiness came on, preceded by a diarrhea-like bowel movement. There was no impairment of speech, but there was some halting…
PIHKALAnthologyShulgin_page_878
tomorrow? What about in the year 2003? Who can tell what will, or will not, be easily available then? There might be a world-wide…
PIHKALAnthologyShulgin_page_879
163 3-TME; 3-THIOMETAESCALINE; 4,5-DIMETHOXY-3-ETHYLTHIOPHENETHYLAMINE) SYNTHESIS: A solution of 13.0 g of…
PIHKALAnthologyShulgin_page_88
I am feeling most benevolent and empathetic. If I do write this, it becomes another tale of power. I must keep my ACTS personal, and…
PIHKALAnthologyShulgin_page_880
solvent removed under vacuum to yield a residue of a colorless oil. This was distilled at 160-170 !C at 1.0 mn/Hg yielding 2.6 g ofa…
PIHKALAnthologyShulgin_page_881
TME, has the sulfur at the 3-position, and by chance, the ethyl group there as well. Here is a brief presentation of the needed Rosetta…
PIHKALAnthologyShulgin_page_882
164 4-TME; 4-THIOMETAESCALINE; 3-ETHOXY-5-METHOXY-4-METHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution of 5.1 g…
PIHKALAnthologyShulgin_page_883
with dry ice. This fraction was recrystallized from 10 mL MeOH, filtered, and washed sparingly with cold MeOH. After air drying, there was…
PIHKALAnthologyShulgin_page_884
165 5-TME; 5-THIOMETAESCALINE; 3-ETHOXY-4-METHOXY-5-METHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution of 10.4 g of…
PIHKALAnthologyShulgin_page_885
the steam bath, then cooled again and stirred for an additional | h. IPA was carefully added to decompose the excess hydride followed by…
PIHKALAnthologyShulgin_page_886
166 2T-MMDA-3a; 3,4-METHYLENEDIOXY- 2-METHYLTHIOAMPHETAMINE SYNTHESIS: A solution of 30 g piperonal in 25 mL cyclohexylamine was brought to…
PIHKALAnthologyShulgin_page_887
1-(3,4-methylenedioxy-2-methylthiophenyl)-2-nitropropene in 10 mL THF was added dropwise, and the stirring was continued for | h. After a…
PIHKALAnthologyShulgin_page_888
deceptively simple terms. We RMOM-ed the hydroxy group of the T-BOC-ed amine.S I have recently heard the above tetramethyl monster referred…
PIHKALAnthologyShulgin_page_889
167 4T-MMDA-2; 6-(22-AMINOPROPYL)-5- METHOXY-1,3-BENZOXATHIOL; 2- METHOXY-4,5- METHYLENETHIOOXYAMPHETAMINE SYNTHESIS: To a well-stirred…
PIHKALAnthologyShulgin_page_89
In any event, these notes stayed completely untouched for a full decade. And it is interesting to see what that decade did bring in the…
PIHKALAnthologyShulgin_page_890
H20 washed and, after sucking as dry as possible, recrystallized from 30 mL boiling MeOH. This provided 1.9 g of 6-formyl-5-methoxy-…
PIHKALAnthologyShulgin_page_891
is the formula to follow. The bottom line is inescapable. None of these extrapolations can hold a candle to the only experiment that can…
PIHKALAnthologyShulgin_page_892
168 TMPEA; 2,4,5- TRIMETHOXYPHENETHYLAMINE SYNTHESIS: To a solution of 39.2 g 2,4,5-trimethoxybenzaldehyde in 160 mL nitromethane there was…
PIHKALAnthologyShulgin_page_893
trimethoxyphenethylamine agrees to a large extent with that of mescaline. However, the new compound had more unpleasant secondary effects…
PIHKALAnthologyShulgin_page_894
169 2-TOET; 4-ETHYL-5-METHOXY-2- METHYLTHIOAMPHETAMINE SYNTHESIS: A mixture of 24.4 g ortho-ethylphenol and 18.9 mL methyl iodide was added…
PIHKALAnthologyShulgin_page_895
85% KOH in 25 mL hot MeOH. The mixture was held at reflux on the steam bath for 1.5 h, and then stripped of volatiles under vacuum. The…
PIHKALAnthologyShulgin_page_896
To a solution of 1.5 g LAH in 30 mL anhydrous THF that was cooled to 0 !C and stirred under a He atmosphere, there was added, slowly, 1.05…
PIHKALAnthologyShulgin_page_897
the usual manner. It was a white crystalline mass that melted at 226-227 !C. It, as with the other 2-carbon analogues of the TOMs and…
PIHKALAnthologyShulgin_page_898
170 5-TOET; 4-ETHYL-2-METHOXY-5- METHYLTHIOAMPHETAMINE SYNTHESIS: A solution of 25 g 3-ethylphenol in 100 mL Et2O was equipped with a…
PIHKALAnthologyShulgin_page_899
standing, the overhead clear solution was decanted from the settled sludge. This hexane solution was stripped of solvent under vacuum,…
PIHKALAnthologyShulgin_page_9
I have tried heroin. This drug, of course, is one of the major concerns in our society, at the present time. In me, it produces a dreamy…
PIHKALAnthologyShulgin_page_90
CHAPTER 15. TENNESSEE My wife, Helen, died on Sunday, September 11, 1977. A few days earlier, she'd had a stroke, a massive pontine…
PIHKALAnthologyShulgin_page_900
mmn/Hg. The fraction with a bp of 102-128 !C weighed 0.4 g and was a colorless liquid. This was dissolved in a small amount of IPA,…
PIHKALAnthologyShulgin_page_901
counterpart is DOM. RTS for RthioS which is the chemical nomenclature term for the replacement of an oxygen atom with a sulfur atom. And,…
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171 2-TOM; 5-METHOXY-4-METHYL-2- METHYLTHIOAMPHETAMINE SYNTHESIS: To a solution of 64.8 g of o-cresol and 56 g dimethyl sulfoxide in 300 mL…
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melted at 135-136 !C. To a slurry of 300 mL cracked ice and 75 mL concentrated H2SO4 in a round- bottomed flask equipped with a reflux…
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Recrystallization from 10 mL boiling MeOH gave 0.7 g of 1-(5-methoxy-4-methyl-2-methylthiophenyl)-2- nitropropene with a mp of 83-84 !C.…
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(with 80 mg) Completely foul taste. The effects were quite subtle, and I found this to be a strange but friendly ++. There was much…
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172 5-TOM; 2-METHOXY-4-METHYL-S- METHYLTHIOAMPHETAMINE SYNTHESIS: To a solution of 6.6 g KOH pellets in 100 mL hot EtOH there was added a…
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boiling MeOH, then with 2x35 mL boiling IPA. Separately, the MeOH extract and the combined IPA extracts, on cooling, deposited 0.6 g each…
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lines reminded me of spectral lines. For a short period of time I thought they were some kind of expression of my energy levels that I…
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173 TOMSO; 2-METHOXY-4-METHYL-5- METHYLSULFINYLAMPHETAMINE SYNTHESIS: A suspension of 12.7 g…
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The next two or three days were chaos, and they will remain largely lost to memory. I cannot recall the details of any of it; the…
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(C12H20CINO2S) C,H. The presence of two chiral centers (the alpha-carbon of the amphetamine side chain and the sulfoxide group at the…
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dose of 60 milligrams of 4-tert-butyl-thioanisole. But then everything fell apart. There was not a detectable trace of anything, neither…
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174 TP; THIOPROSCALINE; 3,5- DIMETHOXY-4-(n)- PROPYLTHIOPHENETHYLAMINE SYNTHESIS: A solution was made of 12.1 g…
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and weighed 0.7 g and was discarded. The second fraction came over at 148-178 !C and weighed 3.0 g. By thin layer chromatography this…
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increased toxicity as well even over the ethyl homologue, TE. The butyl compound (see TB) was the last of this series of phenethylamines…
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175 TRIS; TRESCALINE; TRISESCALINE; 3,4,5-TRIETHOX YPHENETHYLAMINE SYNTHESIS: A solution of 16.9 g of ethyl 3,4,5-triethoxybenzoate in 25…
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400 mL dilute H2SO4. This was washed with 2x75 mL CH2C12, the aqueous phase made basic with aqueous. NaOH, and the product extracted with…
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176 3-TSB; 3-THIOSYMBESCALINE; 3-ETHOXY-5-ETHYLTHIO-4-METHOX YPHENETHYLAMINE SYNTHESIS: A solution of 13.4 g…
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stirring. After 30 min, the reaction was quenched in 500 mL H20, the top hexane layer separated, and the aqueous phase extracted with 2x75…
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removed by filtration, washed with additional Et2O, and air dried to give 0.4 g of 3-ethoxy-5-ethylthio-4- methoxyphenethylamine…
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company of family or friends - to the feelings of optimism and even outright niceness which overtook me now and then, and which I knew…
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177 4-TSB; 4-THIOSYMBESCALINE; 3,5-DIETHOXY-4-METHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution of 12.1 g N,N,NU,NU-tetramethylethylenediamine…
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methylthiophenylacetonitrile, which came over at 135-160 !C, was a yellow liquid, weighed 3.2 g, but did not crystallize. A solution of LAH…
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178 3-T-TRIS; 3-THIOTRESCALINE; 3- THIOTRISESCALINE; 3,4-DIETHOXY-5- ETHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution of 11.5 g…
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was required). The reaction mixture was added to 500 mL H2O containing 4 g sodium hydrosulfite. This was extracted with 3x75 mL petroleum…
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mescaline, although the prototypic compound, was probably going to remain the least potent, it seemed reasonable to use it as a bench mark…
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179 4-T-TRIS; 4-THIOTRESCALINE; 4- THIOTRISESCALINE; 3,5-DIETHOXY-4- ETHYLTHIOPHENETHYLAMINE SYNTHESIS: A solution of 12.1 g…
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separately from 14 mL isopropylamine in 50 mL hexane treated with 60 mL butyllithium solution. There was an immediate darkening of color.…
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(C14H24CINO2S) C,H. DOSAGE: greater than 200 mg. DURATION: unknown. QUALITATIVE COMMENTS: (with 120 mg) Maybe there is some physical…
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dusting off some of the potentially impressive psychedelic compounds which I had toyed with over the past couple of years/ but had not…
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no way of guessing where all this would lead. I excused myself with some muttered words about needing to be alone for a while and rest.…
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[3:50] "Okay again? Not okay again. Was the Vermeer scene out of the window real? Still life? What an intellectually shitty way to commit…
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assurance or ignorance? I remember I had been told that the little light on the respirator came on when she made some effort to breathe for…
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people contributing to that definition, the closer it will be to the truth. Needless to say, there were no more experiments in Tennessee.
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PART TWO
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Part Two: Alice's Voice CHAPTER 16. SPIRAL When I finally gave it a name/1 called it the Spiral. This is how it was. Lying down for nap…