Tryptamine, 5,6-dimethoxy-N-isopropyl-N-methyl · Indole, 5,6-dimethoxy-3-[2-(isopropylmethylamino)ethyl] · 5,6-Dimethoxy-N-isopropyl-N-methyltryptamine · 5,6-Dimethoxy-3-[2-(isopropylmethylamino)ethyl]indole
#41 5,6-MeO-MIPT SYNTHESIS: To a suspension of 0.88 g 5,6-dimethoxyindole in 50 mL Et2O, stirred and cooled with an external ice bath, there was added, dropwise, a solution of 0.87 g oxalyl chloride in 5 mL Et2O over the course of 20 min. The mixture was stirred for an additional 20 min, and then the glyoxyl chloride was removed by filtration, washed with Et2O, and dried under vacuum. A suspension of this red solid in 50 mL of ice-cold dry THF, under nitrogen, was treated with the dropwise addition of a 30% solution of methyl isopropyl amine in Et2O, until the pH exceeded 9. The solvents were removed under vacuum, and the residue partitioned between CHCl3 and H2O. The organic phase, after decolorization with charcoal, was stripped of solvent under vacuum and the solid residue recrystallized from EtOAc/hexane. There was thus obtained 0.61 g 5,6-dimethoxy-N-isopropyl-N-methylindoleglyoxylamide, with mp 204–206 °C (yield 40%).
A well-stirred suspension of 0.55 g LAH in 25 mL anhydrous THF was treated, dropwise, with a solution of 0.53 g 5,6-dimethoxy-N-isopropyl-N-methylindoleglyoxlamide in 75 mL anhydrous THF. The reaction mixture was brought to reflux temperature, held there for 30 min, and cooled to about 40 °C. There was added 0.55 mL H2O followed by 1.65 mL 10% aqueous NaOH and an additional 0.55 mL H2O. The solids were removed by filtration and the filter cake washed with THF. The combined filtrate and washings were stripped of solvent under vacuum. The oily residue was crystallized from hexane to give 0.34 g (yield 71%) 5,6-dimethoxy-N-isopropyl-N-methyltryptamine, mp 71–73 °C. MS (in m/z): C5H12N+ 86 (100%); indolemethylene+ 190 (4%); parent ion 276 (9%).
DOSAGE: >75 mg, orally
DURATION: unknown
QUALITATIVE COMMENTS: (with 35 mg, orally) “Nothing at all.”
(with 75 mg, orally) “There was a vague awareness of something at about the one-hour point. Not enough to even be called a threshold effect.”
EXTENSIONS AND COMMENTARY: This compound, having no detectable activity even at the milligram/kilo level, pretty much condemns the 5,6-dimethoxy indole pattern. Quite a few closely related derivatives have been made; there is the N,N-dimethyl (), the N,N-diethyl (), the N,N-dibutyl () and the three famous heterocyclic ring compounds, the pyrrolidyl (), the piperidyl () and the morpholyl () compounds. They were all synthesized and characterized in the 1960’s, but I have no record of any having been tried in man.
One desoxy analogue warrants mention. This is known as 5-methoxy-6-methyl-DMT () or as 5-methoxy-6,N,N-trimethyltryptamine (5-MeO-6,N,N-TMT), where the 6-methoxy group is, in effect, replaced with a 6-methyl group. Having a skeleton, it was assayed parenterally, and even at 15 milligrams (smoking) there was nothing noted. This is a level that would have been dramatic had there been no substitution at that 6-position. Some of the historical background of an oxygen at this position is discussed in the recipe.
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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