Tryptamine, N,N-dibutyl · Indole, 3-[2-(dibutylamino)ethyl] · N,N-Dibutyltryptamine · 3-[2-(Dibutylamino)ethyl]indole
SYNTHESIS: To a well stirred solution of 10 g indole in 150 mL anhydrous Et2O there was added, dropwise over the course of 30 min, a solution of 11 g oxalyl chloride in 150 mL anhydrous Et2O. Stirring was continued for an additional 15 min during which time there was the separation of indol-3-ylglyoxyl chloride. This intermediate was removed by filtration as used directly in the following step. The above indol-3-ylglyoxyl chloride was added, portionwise, to 20 mL stirred anhydrous dibutylamine. There was then added an excess of 2 N HCl, the mixture cooled, and the resulting solids removed by filtration. These were recrystallized from aqueous EtOH to give, after air drying, 19.7 g (77%) indol-3-yl N,N-dibutylglyoxylamide with a mp 131–132°C.
A solution of 19 g indol-3-yl N,N-dibutylglyoxylamide in 350 mL anhydrous dioxane was added, slowly, to 19 g LAH in 350 mL dioxane which was well stirred and held at reflux temperature under an inert atmosphere. After the addition was complete, refluxing was maintained for an additional 16 h, the reaction mixture cooled, and the excess hydride destroyed by the cautious addition of wet dioxane. The formed solids were removed by filtration, washed with hot dioxane, the filtrate and washings combined, dried over anhydrous MgSO4, and the solvent removed under vacuum. The residue was dissolved in anhydrous Et2O and saturated with anhydrous hydrogen chloride. The solids that formed were recrystallized from benzene/methanol to give 12.6 g (64%) of N,N-dibutyltryptamine hydrochloride (DBT) with a mp of 186–188 °C.
EXTENSIONS AND COMMENTARY: The earliest reports that mention any human responses to DBT suggested that with an i.m. injection of 1 mg/kg there was less effect than with
dihexyl- homologue (DHT) was without any activity at all. The monohexyl homologue (
What kinds of homologues of
indo-3-yl-N,N-diisobutylglyoxylamide and LAH in a manner parallel to the DBT procedure given above. The HCl salt has a mp of 202–204 °C. The pairs of alkyl groups can go on and on forever, but the activity seems to drop off as they get longer. How about a pair of 5-carbon chains? Diamyltryptamine?
And as to trying to name anything higher, such as the N,N-dioctyltryptamine, forget it. The code would have to be, following all this logic,
But the DNA-like triplet code has other complications. What happens when there is just one substituent group on the tryptamine nitrogen atom? Mono-this and mono-that. Monomethyltryptamine has occasionally been called MMT but that might be seen as standing for two methyl groups. In this one case the compound with two methyl groups,
Let me make a table to help unravel the codes used for variously substituted tryptamines. First, there can be things that are never considered in alphabetizing, things that are locators of groups, and they always come first in any code. And, the numbers preceed precede the Greek letters, which preceed the atom symbols, all separated by commas. As examples:
Then comes the name of the compound itself containing, as a rule, either three of four letters. The first letter either tells the number of the groups present, or it can be the first of these groups. As to number:
|N||is for nitrogen to which a single group is attached—indicates mono-substitution|
|D||is for di-substitution|
|T||is for tri-substitution|
As to group names:
|aliphatic alkyl groups||groups with hetero-atoms|
|M||is for methyl||HO||is for hydroxy|
|E||is for ethyl||MeO||is for methoxy (or dimethoxy if preceded by two numbers)|
|P||is for propyl||MeS||is for methylthio|
|IP||is for isopropyl||MDO||is for methylenedioxy|
|B||is for butyl|
|IB||is for isobutyl|
|SB||is for sec-butyl|
|TB||is for tert-butyl|
|A||is for amyl|
|AL||is for allyl|
|H||is for hexyl|
And the last letter defines the class:
|T||is for tryptamine|
|C||is for carboline|
In this way, a monster such as 5,α,N-TTBT becomes, quite obviously, a tryptamine with three tert-butyl groups attached, one at the 5-position, one at the alpha-carbon next to the amine, and one on the amine nitrogen atom itself.
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,
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