Tryptamine, N,N-dimethyl-5,6-methylenedioxy · Indole, 3-[2-(dimethylamino)ethyl]-5,6-methylenedioxy · N,N-Dimethyl-5,6-methylenedioxytryptamine · 3-[2-(Dimethylamino)ethyl]-5,6-methylenedioxyindole · 5H-1,3-Dioxolo-[4,5-f]indole-7-ethanamine, N,N-dimethyl
SYNTHESIS: To a well-stirred, cold solution of 1.61 g 5,6-methylenedioxyindole (see under 2O, 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 dimethylamine was added until the reaction mixture remained basic (pH >9 to external pH paper). The solvents were removed under vacuum, and the 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 ethanol/ethyl acetate EtOAc to yield 1.07 g 5,6-methylenedioxy-N,N-dimethylglyoxylamide
N,N-dimethyl-5,6-methylenedioxy-4-indoleglyoxylamide with a mp 225–226 °C (yield 41%). 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 0.87 g 5,6-methylenedioxy-N,N-dimethylglyoxylamide
N,N-dimethyl-5,6-methylenedioxy-4-indoleglyoxylamide in approximately 100 mL of anhydrous THF. The mixture was brought to reflux temperature, 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 EtOAc/hexane. There was thus obtained 0.30 g 5,6-methylenedioxy-N,N-dimethyltryptamine N,N-dimethyl-5,6-methylenedioxytryptamine (5,6-MDO-DMT), mp 115–117 °C (yield 38%). Anal: C,H,N.
DOSAGE: Greater than 5 mg
QUALITATIVE COMMENTS: (with 5 mg, smoked) “Nothing.”
EXTENSIONS AND COMMENTARY: Up until 15 years ago, there had been no research published describing any simple N,N-disubstituted tryptamines carrying the methylenedioxy substitution pattern on the indole ring. This is interesting in that the activity of the methylenedioxy substituted phenethylamine sort-of
sortof long axis extending through the tryptamine molecule from the 3-position (where the side chain is attached) across the indole ring coming out between the 5- and 6- positions. This certainly feels like the most natural analogue to MDA or MDMA. It has the plus of having the important 5-position occupied, but there might be a bit of a negative effect due to its having something at the 6-position. A more exciting possibility would be the 4,5-disubstitution, which would involve the favorite 5-position along with the site of the oxygen atom of
As to the nature of the nitrogen substituents, this N,N-dimethyl compound is directly analogous to its 5-methoxy or its 5-hydrogen counterparts. In behavioral disruption studies, it is less potent than either of the simpler compounds,
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.
“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.”
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.
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,
Berkeley, CA 94701
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