Tryptamine, N,N-diethyl-2-methyl · Indole, 3-[2-(diethylamino)ethyl]-2-methyl · N,N-Diethyl-2-methyltryptamine · 3-[2-(Diethylamino)ethyl]-2-methoxyindole
#33 2-Me-DET SYNTHESIS: To an ice-cold and stirred solution of 6.56 g 2-methylindole in 75 mL TBME there was added, over the course of 20 min, 35 mL of a 2.0 M solution of oxalyl chloride in CH2Cl2. The glyoxyl chloride formed immediately and was removed by filtration and washed with 20 mL cold TBME. A solution of 16 mL diethylamine in 50 mL CH2Cl2 was prepared, cooled in an external ice bath, and vigorously stirred. To this, the solid glyoxyl chloride was added in small increments producing a yellow solution. The reaction mixture was washed successively with H2O, 0.5 N HCl, and again with H2O. After drying over anhydrous Na2SO4, the solvent was removed under vacuum providing an orange solid as residue. This was recrystallized from boiling THF and, after filtration and air drying to constant weight, provided N,N-diethyl-2-methylindoleglyoxamide N,N-diethyl-2-methylindoleglyoxylamide with a mp 170–172 °C.
To a stirred and cooled solution of 7.4 g N,N-diethyl-2-methylindoleglyoxamide N,N-diethyl-2-methylindoleglyoxylamide in 80 mL dry toluene under an inert atmosphere, there was added 31 mL 65% Red-Al in toluene, at a slow rate. After 20 min the ice bath was removed and the reaction allowed to stir for 2 h, and finally an additional 3 h at 60 °C. The light yellow solution was cooled again in the ice bath, and the excess hydride destroyed by the slow addition of 15 mL IPA followed by 50 mL H2O. The solids were removed by filtration and washed with toluene. The combined filtrate and washings were repeatedly washed with H2O and then extracted twice with 0.5 N HCl. The aqueous extracts were pooled, washed with CH2Cl2, and made basic by the addition of 25% NaOH. The precipitate that formed was extracted into several small portions of CH2Cl2 which were pooled and dried with anhydrous Na2SO4. After removal of the drying agent, the solvent was removed under vacuum. To the residue there was added a 1.0 M solution of HCl in anhydrous Et2O until the mixture was neutral as determined by external damp pH paper. The resulting solid was removed by filtration and twice recrystallized from a MeOH/acetone mixed solvent. There was thus obtained N,N-diethyl-2-methyltryptamine hydrochloride (2-Me-DET) as white crystals with a mp 214–216 °C.
DOSAGE: 80–120 mg, orally
DURATION: 6–8 hrs h
QUALITATIVE COMMENTS: (with 70 mg, orally) “A very subtle onset characterized most notably as a mild stomach ache that lasted a short while. There was a sort of vague unreal feeling at an hour, but my thought pattern seemed to be quite clear. In another hour I noticed that higher pitches of the music on the radio were being muffled and the tones seemed to be shifting to lower frequency. I phoned a friend, and first the dial tone, and then her voice sounded wrong. The sense of touch (the phone receiver) was normal and my conversation flowed easily. Television seems amusing, but perhaps it really was amusing. Soup tasted fine, and there was no appetite suppression. No GI problems, no next-day negatives.”
(with 120 mg, orally) “My thoughts became quite cloudy, increasingly so for several hours. And somehow slower than usual. Reading didn’t seem to connect, and I had to turn the radio off as it was lousy. Texture, not content. I could type OK, and did, so my body was OK, but things came to me slowly. I wasn’t very hungry but food tasted OK. The ‘cloudy’ was pretty much gone after six hours. I don’t particularly want to repeat this, as there isn’t much here that I enjoy.”
EXTENSIONS AND COMMENTARY: There is an interesting idea tucked away here in what seems to be an uninteresting compound.
The sound distortion, mentioned in both of these reports, brings to mind where it is the major indicator of intoxication. With some people, it is the only change observed. With DIPT, there are two isopropyl groups on the basic nitrogen atom; here there are two ethyl groups. One might speculate that there might well be some optimum group geometry that would make the auditory to visual distortion ratio as high as possible. There were no suggestions that there were any auditory changes with so perhaps the added mass of that methyl group at the 2-position brings the molecular weight into some “auditory window.” A compelling compound would be, of course, N,N-diisopropyl-2-methyltryptamine (2-Me-DIPT), but I don’t believe that it has ever even been synthesized as of the present moment. It would certainly be a simple compound to make from the above indole.
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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