Tryptamine, N,N-diisopropyl-4,5-methylenedioxy · Indole, 3-[2-(diisopropylamino)ethyl]-4,5-methylenedioxy · N,N-Diisopropyl-4,5-methylenedioxytryptamine · 3-[2-(Diisopropylamino)ethyl]-4,5-methylenedioxyindole · 5H-1,3-Dioxolo-[4,5-e]indole-7-ethanamine, N,N-diisopropyl
SYNTHESIS: A solution of 4.8 g 4,5-methylenedioxyindole (see under for its preparation) in 60 mL anhydrous Et2O was stirred and cooled with an external ice bath. There was added, dropwise, a solution of 5.0 g oxalyl chloride in Et2O so that the temperature did not exceed 5 °C. The intermediate acid chloride separated as a red solid, and was removed by filtration and washed with Et2O. It was then suspended in 60 mL cold anhydrous Et2O, treated with 14 mL diisopropylamine and the mixture stirred for 30 min. The solvent was decanted from the crude solids that formed, and they were suspended in 50 mL H2O. The product was removed by filtration and vacuum dried to provide 5.3 g (56%) 4,5-methylenedioxy-N,N-diisopropylindole-3-glyoxylamides a N,N-diisopropyl-4,5-methylenedioxyindole-3-glyoxylamide as white solid, with a mp 260 °C (dec).
To a stirred and cooled solution of 3.8 g LAH in 100 mL anhydrous THF there was added, over the course of 1 h, a solution of 4.70 g 4,5-methylenedioxy-N,N-diisopropylindole-3-glyoxylamide N,N-diisopropyl-4,5-methylenedioxyindole-3-glyoxylamide in 500 mL anhydrous THF. After 1 h reflux, the cooled reaction mixture was treated with 3.8 mL H2O, followed by 3.8 mL aqueous 5% NaOH and then by an additional 10.4 mL H2O. The solids were removed by filtration and washed with THF. The combined filtrate and washings were dried (MgSO4) and the solvent removed under vacuum. The residual oil was distilled at the KugelRohr (0.5 mm/Hg at 100 °C) to give a distillate that solidified. This was crystallized from benzene/hexane to provide 1.34 g (31%) of 4,5-methylenedioxy-N,N-diisopropyltryptamine N,N-diisopropyl-4,5-methylenedioxytryptamine (4,5-MDO-DIPT) with a mp 109–113 °C. Anal: C, H. N.
DOSAGE: >25 mgs mg, orally
DURATION: unknown
QUALITATIVE COMMENTS: (25 mg, orally) Nothing much happened for about 3 hours, and then I suddenly shot up. I was at the plateau for a fair time, the recovery was difficult to define chronologically. This was in daylight; I was reminded very much of .
EXTENSIONS AND COMMENTARY: This is the second of the two tryptamines known with the most appealing methylenedioxy ring bridge located at the two most sensitive ring positions of the indole nucleus. It, too, is an unknown entity. There is a single observation of an oral trial, and it suggests something of interest at 25 milligrams. Higher dosages might prove most interesting. There is no question that the methyl isopropyl homologue of this compound, 4,5-MDO-MIPT would be a rewarding compound to assay. As of the present moment, it has not yet been synthesized. It should be a relatively easy one to make.
There is an interesting parallel to be seen here. This methylenedioxy hetero-ring is snuggled as closely as possible to the ethylamine chain of the indole (the 4-position occupied by the nearer oxygen atom, and the indole chain at the 3-position). There is the same intimacy possible in the phenethylamine world. This would be realized by moving the methylenedioxy ring of (3,4-methylenedioxyamphetamine) to the 2,3-location. Here, again, the nearer oxygen would be as close as possible to the ethylamine chain at the 1-position. This compound, , has been made by several research groups, and has been looked at in man. At 50 milligrams, orally, it produced some pretty strong stimulatory effects, with no sleep found to be possible during the following 24 hours. But, on the other hand, it seemed to be devoid of MDA-like effects. This positional isomer was mentioned in PiHKAL.
There is no way to meaningfully extrapolate from this phenethylamine analogue 2,3-MDA to 4,5-MDO-DIPT, but it does present a very close structural relationship that could be used to justify a clinical study of this unusual tryptamine.
13 May 2016 · · Isomer Design
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.”
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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