Tryptamine, N-ethyl-4-hydroxy-N-methyl · 4-Indolol, 3-[2-(ethylmethylamino)ethyl] · N-Ethyl-4-hydroxy-N-methyltryptamine · 3-[2-(Ethylmethylamino)ethyl]-4-indolol
#21 4-HO-MET 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 methylethyl 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 Et2O to give 0.60 g (yield 73%) of 4-acetoxyindol-3-yl-N-ethyl-N-methylglyoxylamide with a mp 179–180 °C. Anal: C,H,N.
To 10 mL of a stirred solution of LAH (1 M in THF under N2), there was added dropwise a solution of 0.57 4-acetoxyindol-3-yl-N-ethyl-N-methylglyoxylamide in 10 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 solid residue recrystallized from EtOAc/hexane to provide 0.18 g (41%) N-ethyl-4-hydroxy-N-methylindole (4-HO-MET) with a mp 118–119 °C. Anal: C,H,N.
DOSAGE: 10–20 mg, orally
DURATION: 4–6 hrs h
QUALITATIVE COMMENTS: (with 20 mg, orally) "Qualitatively a lot like . I started within the first half-hour, and at the max, I felt the same alteration of color and form, and times, sound was felt. As with , the experience was wave-like, with an alteration of effects between near-normal perception at one minute, only to be swept up in a swirl of altered concept concepts the next minute.
EXTENSIONS AND COMMENTARY: First, an apology for just a single entry in the comments section. This, and several other of these substituted hydroxy and methoxy tryptamines, had had earlier evaluations, but the notes are not at hand and cannot be used. Much will have to come back from memory, and there must be an appropriate fuzziness allowed for the concluded generalization as to dose and duration. With this particular compound, some of the original observations suggested that it was more potent than , certainly more dramatic. But at the bottom line, I doubt that this ethyl homologue, or the isopropyl homologue 4-HO-DIPT for that matter, could be distinguished from the methyl counterpart in any blind clinical study.
What’s to choose between them? From the view-point of synthesis, the cost and availability of the secondary amine will certainly be a factor. Both methylethyl amine and methylisopropylamine are available, but are quite expensive. Dimethylamine, on the other hand, is dirt cheap but it is a recognized precursor to and thus is difficult to find. In any events, the dimethyl compound is widely available in the mycological arena, and I suspect it would be simplest to stay with nature.
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,
Box 13675
Berkeley, CA 94701

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