Indole, 3-[2-(diisopropylamino)ethyl]-5,6-methylenedioxy · Tryptamine, N,N-diisopropyl-5,6-methylenedioxy · N,N-Diisopropyl-5,6-methylenedioxytryptamine · 3-[2-(Diisopropylamino)ethyl]-5,6-methylenedioxyindole · 5H-1,3-Dioxolo-[4,5-f]indole-7-ethanamine, N,N-diisopropyl
#29 5,6-MDO-DIPT SYNTHESIS: To a well stirred, cold solution of 1.61 g 5,6-methylenedioxyindole (see under for its preparation) in 20 mL anhydrous Et2O, there was added dropwise a solution of 1.75 mL oxalyl chloride in 5 mL Et2O. The addition took 20 min. After an additional 20 min stirring in the external ice bath, the red crystals that formed were removed by filtration, washed with 2×5 mL Et2O, and dried under vacuum for 0.5 h. This crude acid chloride was dissolved in 100 mL anhydrous THF and cooled, under N2, to 0 °C. An Et2O solution of diisopropylamine was added until the reaction mixture remained basic (pH >9 to external pH paper). The solvents were removed under vacuum, and residue treated with 100 mL each of H2O and CHCl3. The organic phase was separated, the aqueous phase extracted with additional CHCl3, the pooled extracts dried over anhydrous MgSO4, filtered, and the filtrate evaporated under vacuum. The residue was recrystallized from ethyl acetate/hexane to yield 1.20 g 5,6-methylenedioxy-N,N-diisopropylglyoxylamide N,N-diisopropyl-5,6-methylenedioxyindol-3-ylglyoxylamide with a mp 278–280 °C (38%). Anal: C,H,N.
To a well stirred suspension of 0.77 g of LAH in 40 mL dry THF, there was added dropwise a solution of 0.95 g 5,6-methylenedioxy-N,N-diisopropylglyoxylamide N,N-diisopropyl-5,6-methylenedioxyindol-3-ylglyoxylamide in approximately 100 mL of anhydrous THF. The mixture was brought to reflux temperature and held there for 2 h, and allowed to return to room temperature. It was hydrolyzed by the cautious addition of 0.8 mL H2O, followed with 2.4 mL 10% aqueous NaOH, and finally an additional 0.8 mL of H2O. The inorganics were removed by filtration through Celite, and the filtercake was washed with additional THF. After removal of the solvent of the combined filtrate and washings under vacuum, the residue was distilled by KugelRohr and the colorless distillate recrystallized from a mixture of Et2O/hexane. There was thus obtained 0.52 g 5,6-methylenedioxy-N,N-diisopropyltryptamine N,N-diisopropyl-5,6-methylenedioxytryptamine (5,6-MDO-DIPT) with a melting point of 93–94 °C (60%). Anal: C,H,N.
DOSAGE: unknown
DURATION: unknown
EXTENSIONS AND COMMENTARY: So why enter an entry into a listing of active compound when it is simply not known if it is active or not? The truth is, that none of these three 5,6-methylenedioxy-N,N-disubstituted tryptamines (this one, or or ) has been explored up to an active level, but they are appealing targets in that they have the progression of nitrogen substituents that has proven so valuable in similar sequences of compounds. This is the pattern dimethyl, methylisopropyl and diisopropyl. With both the unsubstituted, and the 5-methoxy-substituted groups, the activity goes from quite potent but requiring parenteral administration, to highly potent and orally active, and back to quite potent and orally active, as the methyl groups are progressively replaced with isopropyl groups. It would be instructive to see if this arrangement was maintained with this methylenedioxy trilogy.
The three closed ring group of substituents mentioned in the recipe have also been described with this 5,6-methylenedioxy ring substitution. These could be named 5,6-MDO-pyr-T (the pyrrolidine analogue, mp 110–112 °C), 5,6-MDO-pip-T (the piperidine analogue, mp 150–152 °C) and 5,6-MDO-mor-T (the morpholine analogue, mp 117–119 °C). To my knowledge, none of these has ever been put into man.
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.
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