Tryptamine, N-isopropyl-5-methoxy-N-methyl · Indole, 3-[2-(isopropylmethylamino)ethyl]-5-methoxy · N-Isopropyl-5-methoxy-N-methyltryptamine · 3-[2-(Isopropylmethylamino)ethyl]-5-methoxyindole
SYNTHESIS: To a solution of 1.40 g 5-methoxy-N-methyltryptamine (celite Celite, the filtrate stripped of solvent under vacuum, and the solid residue recrystallized from Et2O/hexane to give 1.45 g N-isopropyl-5-methoxy-N-methyl-tryptamine (5-MeO-MIPT). This was isolated as the hydrochloride salt by dissolving it in a small amount of IPA, neutralization with concentrated HCl, and dilution with Et2O. This had a mp 162–163 °C. Anal: C15H23ClN2O. C,H,N. MS (in m/z): C5H12N+ 86 (100%); indolemethylene+ 160 (5%); parent ion 246 (4%).
4–6 mg, orally;
12–20 mg, smoked
12–20 mg, smoked
DURATION: 4–6 hrs h
QUALITATIVE COMMENTS: (with 1.5 mg, orally) “In 15 minutes I was already off of baseline, and by an hour it is unquestionably real. There is no visualization to music, but a general turned-on randiness. Dropping at an hour and a half, and out by three hours. Modest but real.”
(with 4 mg, orally) “Up very fast, to a +2 in an hour. Absolutely no visuals, but over the next two hours an ease of interpretive fantasy, almost dream-like, and easy eroticism. Food tasted marvelous, but there was no appetite. Easy, normal sleep and good spirits in the a.m.”
(with 5 mg, orally) “Extremely bitter taste. Some stimulation and tingling at 10 minutes, and I am apprehensive at this rapid onset. There are no visual symptoms at all, but the stimulation of conceptual thought is intense. Depth perception is slightly altered and a very minor wave pattern can be noticed in the peripheral vision, but no major object or color distortion. Minor enhancement of auditory acuity. Philosophical concepts about this and other substances seem important. I wonder what the value of writing about, or attempting to describe, their effects really is. At the second hour, the effects are subsiding, and for another three hours there are tailings and insomnia, but I am able to eat normally. There is a certain amount of ‘negativity’ about this compound. The dose is satisfyingly small, but I wonder if it is worth it. Somewhat of a disappointment. Have no desire to experiment further.”
(with 6 mg, orally) “Rapid development to 45 minutes, some shakes, uneven handwriting, and hints of time slowing. Extremely erotic. Full plateau at a +3 at the 2 1/2 hr. point, then a graceful and rather rapid drop. Easy, restful sleep. Absolutely no visuals or related sensory effects—what does one call this stoned state? Very pleasant, music extremely acceptable, tactile extraordinary. I feel that higher dosages would not contribute anything more.”
(with 12 mg, smoked) "I was able to take 4 or 5 puffs, and to hold off the onset until then, then I couldn’t anymore. Powerful, tremendous rush, but all along maintaining body-ego awareness, unlike
"At an hour and a half, I was down enough that I tried smoking the remainder of the bowl without much additional effect. A typical psychedelic afterglow and in the morning ate a big breakfast and felt essentially normal. In summary, I took too little, I was in a bad mood, and felt myself to be in a rushed environment. The experience seemed to me like a hybrid between
(with 20 mg, smoked) "Most all of it was smoked in about three or four inhalations before I felt it coming on so strongly that I lay down. Within less than a minute after I lay down, with my eyes closed, my visual field was filled with brilliant geometric patterned lines of different colors that were slowly moving. There were several sets of parallel and curved lines superimposed upon in each other. Soon after that, probably within a minute or two, I became extremely disoriented from my normal sense of being a person in a body; I was lost in an undifferentiated mass of feeling and non-specific sensation. It was similar to the overwhelming feeling of
"Then I began to think more coherently, but intense waves would return every 5 to 15 minutes. In between my perception and thinking would be fairly normal, but with the waves I would be swept up in imagery or memories heavily laden with emotional content. After two hours I was joined by my wife. We spent some very intimate time together, and I remember asking her who she was and she replied, ‘Your wife.’ This was very powerful to me since I did not really know what it meant, except that it seemed to be the best combination of mother, lover and friend, and that it was an entirely new kind of relationship that we would be creating for the rest of our lives together.
“After three or four hours, the waves had virtually stopped, and I remained oriented to the present and my immediate surroundings. I stayed under a mild influence until I ate supper, around 7 hours. I felt tired, had trouble falling asleep, but awoke refreshed.”
EXTENSIONS AND COMMENTARY: In my lecturing at the University, every couple of years or so some student uses the term “more unique than” or “relatively unique.” This immediately triggers a reflex response from me, to emphasize the simple definition that something that is unique is something that is one of a kind, and that all one-of-a-kind things are different from all other one-of-a-kind things. All drugs are unique. Every drug is different from all other drugs. 5-MeO-MIPT is unique.
The last two entries in the “Qualitative Comments” section are longer than usual, but even at that they have been trimmed down from reports sent to me that were each of over three pages in length. A thread common to each of them, is the comparison of the effects of smoking 5-MeO-MIPT to those from smoking
All you need to do, to see that clearly, is to look at that one additional observation involving oral activity. This drug, 5-MeO-MIPT, is several times more potent when taken orally than it is when smoked.
Might the observations of the remaining oxygen-substituted MIPT’s provide additional clues? There are four possible mono-methoxylated MIPT’s; all have been synthesized and all have been explored in man. The
5H12N+ 86(100%); indolemethylene+ 160 (7%); parent ion 246 (4%). In human trials there was one report of some kind of neurological twinge at a 16 milligram level, but nothing else at trials of up to 50 milligrams and it has been shelved as being inactive.
The isomeric 5H12N+ 86 (100%); indolemethylene+ 160 (5%); parent ion 246 (4%). Gas chromatographic analysis indicated that the product was only 80% pure, and three of the impurities were identified. One was 4H10N+ 72 (100%); indolemethylene+ 161/160 (13, 8%); parent ion 232 (4%). Another was 3H8N+ 58 (100%); indolemethylene+ 160 (6%); parent ion 218 (9%). The third was 2H6N+ 44 (100%); indolemethylene+ 161/160 (82, 39%); parent ion 204 (5%). These three impurities represented approximately 5%, 3%, and 4%, resp., of the isolated product’s final weight. It showed something going on at 20 mg orally with perhaps a little distortion in the visual field. And, separately, at 70 milligrams orally there might have been a light-headedness after a few minutes. Nothing more. It, too, has been given the kiss of death by being declared inactive at the 50 milligram level.
The last of the Mohicans, the tribe of compounds with the remarkably potent, orally active, N-methyl-N-isopropyl system on the tryptamine nitrogen atom, was the dimethoxy analogue with both the 5- and the 6-positions occupied with methoxy groups. This specific compound has its own recipe as it raises specific questions that deserve direct attention. The very close relative with the methylenedioxy group at this 5,6-location also has a separate recipe.
Two final laments. Remember that all these beautiful compounds are unique. Why do they behave the way they behave? I have no idea and there is never enough data to explain everything. I hate the fact that the word data is plural. But singular or plural keep collecting it (them), and keep trying to make sense of everything. And, a small point from my infancy. The Last of the Mohicans was one of the very first books I read, and I had very innocently accepted the footware footwear of these Indians as being the metaphor for the people themselves. I had seen that title as having been, “The Last of the Moccasins.” This is a pair of words that I still interchange without any defense, along with shoulder and soldier, avatar and atavar, and especially annoying when lecturing, irrelevant and irreverent.
About TiHKAL · info
This version of Book II of TiHKAL is based on the Erowid online version created by Bo Lawler with the help of Erowid, from content generously provided in electronic format by the Authors.
The Erowid online version does not always align precisely with the printed version. Text appears to have been inserted, deleted, or changed at various points. Where the two are seen to diverge both the Erowid and print versions are given. Sharp-eyed readers are encouraged to report novel discrepancies.
As with PiHKAL, I’ve again attempted to reproduce the typographic style of the printed edition. I’ve again made minor changes to some chemical names in line with current nomenclature practice. Typically the change is little more than expanding a prefix or setting it in italics. The history page has further details.
“At the present time, restrictive laws are in force in the United States and it is very difficult for researchers to abide by the regulations which govern efforts to obtain legal approval to do work with these compounds in human beings.“No one who is lacking legal authorization should attempt the synthesis of any of the compounds described in these files, with the intent to give them to man. To do so is to risk legal action which might lead to the tragic ruination of a life. It should also be noted that any person anywhere who experiments on himself, or on another human being, with any of the drugs described herein, without being familiar with that drug’s action and aware of the physical and/or mental disturbance or harm it might cause, is acting irresponsibly and immorally, whether or not he is doing so within the bounds of the law.”
The copyright for Book I of TiHKAL has been reserved in all forms and it may not be distributed. Book II of TiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.
TiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of tryptamines. This book belongs in the library of anyone seeking a rational, enlightened and candid perspective on psychedelic drugs.
Though Sasha and Ann have put Book II of TiHKAL in the public domain, available to anyone, I strongly encourage you to buy a copy. We owe them — and there’s still nothing quite like holding a real book in your hands.
TiHKAL (ISBN 0-9630096-9-9) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.Transform Press,
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