Tryptamine, 4-hydroxy-N-isopropyl-N-methyl · 4-Indolol, 3-[2-(isopropylmethylamino)ethyl] · 4-Hydroxy-N-isopropyl-N-methyltryptamine · 3-[2-(Isopropylmethylamino)ethyl]-4-indolol
SYNTHESIS: A solution of 0.50 g 4-acetoxyindole (see under 2O was stirred and cooled to 0 °C with protection from atmospheric moisture. There was then added 0.5 mL oxalyl chloride. The reaction mixture was stirred for an additional 30 min, and the yellow crystalline solid was removed by filtration and dissolved in 10 mL of anhydrous THF. This was treated with a 40% solution of methyl isopropylamine in dry Et2O, dropwise, until the pH of the reaction mixture was >10. The solvents were removed under vacuum and the residue dissolved in 200 mL CHCl3. This was washed first with 50 mL 0.1 N HCl and then with 50 mL of saturated aqueous NaCl. After drying with anhydrous MgSO4 and filtration, the solvent was removed under vacuum. The residue was recrystallized from CHCl3/hexane to give 0.68 g 4-acetoxyindol-3-yl-N-isopropyl-N-methylglyoxylamide with a mp 211–212 (79%).
To 10 mL of a stirred solution of LAH (1 M in THF under N2), there was added dropwise a solution of 600 mg 4-acetoxy-N-methyl-N-isopropylindole-3-glyoxylamide 4-acetoxyindol-3-yl-N-isopropyl-N-methylglyoxylamide in 10 mL anhydrous THF. When the addition was complete, the reaction mixture was brought to a reflux on the steam bath for 15 min. After cooling to 40 °C, sufficient water was added to decompose both the reaction complex and the excess hydride. After filtration through Celite (under an N2 atmosphere), the solvent was removed under vacuum, and the solid residue recrystallized from EtOAc/hexane. There was thus obtained 340 mg .34 g (74%) of 4-hydroxy-N-methyl-N-isopropyltryptamine (4-HO-MIPT) with a mp of 123–124 °C. 4-HO-MIPT discolors quickly if it is not kept in an inert atmosphere and in a freezer. Anal: C,H,N.
DOSAGE: 12–25 mg, orally (as the indolol or the acetate)
DURATION: 4–6 hrs h
QUALITATIVE COMMENTS: (with 9 mg, orally) “I am stuck just part way on. There is some retinal activity with my eyes closed. Maybe I am a little light-headed, a little starry. Nothing much.”
(with 12 mg, orally) “It was just an hour ago that I swallowed the capsule, and everything is happening. I was completely developed at 45 minutes. The imagery with my eyes closed is vivid. The music is exceptionally sensual. I notice a tendency to twitch but it doesn’t bother me. Everything is rolling—how can they allow an erotic piece like the Saint Saëns second piano concerto to ever appear in public, let alone over the radio? A very rapid decline between the third and fourth hour. A rich day for love, insights, fantasy and for retreating into one’s mind. A rich day for discovery.”
(with 12 mg, orally) “I suspended the solids in water, and a drop of HCl put it into solution immediately. The first awareness was unmistakable at twenty minutes, and from there it was a rapid and noisy development ending at about an hour. But this lasted for only another 40 minutes, and then dropped off quite rapidly. The erotic was excellent, but there were few visuals and I had difficulty connecting fantasy to music. Good appetite afterwards, and I had no trouble getting to sleep.”
(with 15 mg acetate ester, orally) “An interesting mixture of intoxication and sedation, progressing to a very relaxed state with some motor incoordination. Just a little bit like alcohol or GHB. There was no drifting of thoughts nor any gut disturbance at any time, although I wasn’t very hungry. Conversation was easy.”
(with 20 mg, orally) “Early signs (muscle sensations) were noticed in 10 minutes. In another 10 minutes a rapid heightening of all senses ensued, reaching a plateau in 40 minutes and beginning to decline in 3 hours with a return to near normal in 5–6 hours. The intensity of the experience is marked. At the plateau, communication (verbal) is difficult with intense alteration in the sense of time and distance. Multiple and overlapping wave forms occur with an extremely intense color alteration. Drifting in and out of the body is common with an increased sense of body processes, i.e., blood flow in vessels. Muscular sense is increased and a feeling of soaring in bodiless flight is experienced. A mild vertigo was felt with attempted walking but is not associated with nausea. Some anxiety was experienced initially, but could be interpreted as a reaction to the extremely powerful onset. A curious, probably idiosyncratic effect, was of possessing the essence of sexual power associated with being a large jungle cat. The idea was prominent for some time. Conservatively, this compound is at least twice as active as
(with 30 mg acetate ester, orally) “It was as if I had downed a few martinis in a hurry—except that there were eye-closed visuals in a lot of different colors, especially metallic greens. I had jaw clenching and a body tremor, reminding me of
EXTENSIONS AND COMMENTARY: This is a two-carbon homologue of
Here, as with the
A large number of related homologues of structurae structural activity relationship gestalt to selectively, and specifically, evaluate the geometric nature of the nitrogen substituents.
If one were to be a complete perfectionist in these areas of chemistry, one should actually make the phosphate ester of 4-HO-MIPT, as this would be the exact homologue of
A careful clinical comparison of the acetate ester of
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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