Tryptamine, 4-hydroxy-N-methyl-N-propyl · 4-Indolol, 3-[2-(methylpropylamino)ethyl] · 4-Hydroxy-N-methyl-N-propyltryptamine · 3-[2-(Methylpropylamino)ethyl]-4-indolol
#23 4-HO-MPT SYNTHESIS: A solution of 0.50 g 4-acetoxyindole (see under for its preparation) in 5 mL Et2O 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 methylpropyl amine in anhydrous Et2O, dropwise, until the pH 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 EtOAc/hexane to give 0.54 g (63%) of 4-acetoxyindol-3-yl-N-methyl-N-propylglyoxylamide with a mp 94–95 °C. Anal: C,H,N.
To 8 mL of a stirred solution of LAH (1 M in THF under N2), there was added dropwise a solution of 0.48 4-acetoxyindol-3-yl-N-methyl-N-propylglyoxylamide in 8 mL anhydrous THF. When the addition was complete, the reaction mixture was brought to a reflux 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 oily residue dissolved in MeOH, neutralized with HCl, and Et2O added until crystallization started. Thus there was obtained 0.23 g (54% of theory) 4-hydroxy-N-methyl-N-propylindole 4-hydroxy-N-methyl-N-propyltryptamine hydrochloride (4-HO-MPT) with a mp 162–163 °C. Anal: C,H,N.
DOSAGE: unkown unknown
DURATION: unknown
QUALITATIVE COMMENTS: (with 8 mg, orally) “There was a very mild visual distortion, and a prominent vertigo without nausea. In the second hour there is still some enhancement of visual detail, but I am not endowed with the flight of ideas of philosophical concepts as with . I am rapidly subsiding and I am able to eat normally. Residual insomnia lasted eight hours.”
EXTENSIONS AND COMMENTARY: As with the discussion presented with the lower homologue, , there is not enough here to give a fair estimate of either dose or duration. In my file under this compound I can fine find only this one report. Extrapolation suggests that this might be yet another material active in the range of somewhere up to 20 milligrams, all orally. Maybe it is a generality that anything with up to six carbons attached one way or another to the tryptamine nitrogen atom (and all sporting a 4-hydroxy group, of course) will be active in the 10 to 20 milligram range. This certainly holds for the methyl-methyl, methyl-ethyl, methyl-propyl, methyl-isopropyl, diethyl, dipropyl and diisopropyl. That makes it a pretty good generalization.
How far can this argument be pushed? What about one of the N-alkyl groups having four carbons? Keeping the other N-alkyl group as the smallest and most simple methyl group, all four isomeric compounds are known. There is the n-butyl isomer (, an oil), the isobutyl isomer (, mp 142–145 °C), the secondary butyl isomer (, mp 138–140 °C) and the tertiary butyl isomer (, mp 225–226 °C). Of these four materials only 4-HO-MTBT has been looked at as a possible psychedelic. Some 15 milligrams produced virtually no effects, maybe a hint of something in a few minutes and then nothing. Probably pure placebo.
Many yet heavier substitution patterns are in the literature but they, too, are unexplored. The symmetrical disubstituted isomers are listed separately in these recipes.
13 May 2016 · Creative Commons BY-NC-SA ·

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.

Cautionary note

“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.”
Alexander T. Shulgin

Copyright notice

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.

Ordering information

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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