Tryptamine, N-butyl-N-methyl · Indole, 3-[2-(butylmethylamino)ethyl] · N-Butyl-N-methyltryptamine · 3-[2-(Butylmethylamino)ethyl]indole
SYNTHESIS: To a well-stirred, ice cold solution of 5.0 g indole in 75 mL TBME, there was added a solution of 6.35 g oxalyl chloride in 25 mL CH2Cl2 dropwise over the course of 15 min. Stirring was continued for an additional 10 min, and the resulting solids were removed by filtration and washed with 15 mL cold TBME. This solid amide was, in turn, added portionwise over a period of 10 min to a well stirred, ice cold solution of 15 mL N-methyl-butylamine N-butyl-N-methylamine in 100 mL CH2Cl2. The clear red solution that resulted was stirred for a few additional minutes, washed in sequence with H2O, 1% aqueous hydrochloric acid, and then H2O. Following drying with solid anhydrous Na2SO4, the solvent was removed under vacuum, yielding a thick red oil. Upon dilution with 20 mL cold EtOAc an off-white solid was produced. This was recrystallized from 100 mL boiling EtOAc producing, after cooling, filtering and air-drying to constant weight, 5.82 g of
N-butyl-N-methyl-indoleglyoxylamide with a melting point of 128–130 °C. A second crop of 0.6 g was obtained from the filtrate, for a total yield of 58%.
A stirred suspension of 6.3 g of
N-butyl-N-methyl-indoleglyoxylamide in 150 mL dry toluene, in a three-neck round bottomed flask and under a N2 atmosphere, was cooled with an external ice bath. A total of 30 mL of a 65% Red-Al solution in toluene was added slowly by syringe, and there was immediate gas evolution. After the addition was complete, the stirring was continued for an hour, then the flask was gradually warmed to 40 °C, and the stirring continued for an additional 2 h. After cooling again to ice temperature, the excess Red-Al was decomposed by the drop-wise addition of first IPA followed by (after conspicuous gas evolution had ceased) H2O. The inorganic aluminum salts were removed by filtration of the resulting suspension, and the filter cake was washed with isopropyl acetate. The filtrate and washings were combined and washed thoroughly with H2O. The product was then extracted into 1 N hydrochloric acid, the pooled extracts washed twice with CH2Cl2, made basic with 20% aqueous KOH and extracted with CH2Cl2. After washing with H2O and drying with anhydrous Na2SO4, the solvent was removed under vacuum to yield a light yellow oil with a bluish florescence. The free amine did not crystallize but was dissolved in MeOH and titration to a slightly basic end-point with a methanolic solution of fumaric acid. The solution was heated to the boiling point, and slowly diluted with two volumes of hot isopropyl acetate. Slow cooling yielded beautiful light yellow crystals of N-butyl-N-methyl-tryptamine fumarate (MBT). A recrystallization from MeOH/isopropyl acetate gave 5.83 g (69%) of product with a mp 148–150 °C.
DOSAGE: 250–400 mg
DURATION: 4–6 hrs h
QUALITATIVE COMMENTS: (with 130 mg, orally) “Perhaps a subtle intoxication at two hours, and certainly nothing at five hours.”
(with 175 mg, orally) “Some mild incoordination and concentration difficulties, all trivial, and a good sleep and a good day the next day.”
(with 250 mg, orally) “At 75 minutes there was the prompt development of an intoxicated state primarily characterized by fine motor impairment. Nothing remotely resembling any type of hallucination. Appetite was normal and food and water were consumed without difficulty. Most activities were uninteresting, even dull. The effects lasted about five hours.”
(with 400 mg, orally) “It hit an just over an hour, and it quickly became difficult to keep both eyes focused on the point of gaze. There was no actual double vision, but things were not quite right. In a few more minutes an apparent motion became apparent with fixed objects, and shortly thereafter there was a faint ‘retinal circus’ that was reminiscent of
EXTENSIONS AND COMMENTARY: This is a pretty heavy body trip for a modest mental return. As with any tertiary amine, one cannot help but speculate what role the deamination enzyme systems of the liver are compromising the results that are being experienced. Here is a compound with five aliphatic carbon atoms hanging out there on the basic nitrogen. No branched chain; everything straight chain. How does this be compared with other tryptamines with straight-chain on that nitrogen atom? P. harmala maybe) and see if there can be more mental effects and fewer toxic effects at a lower dose exposure. There is certainly good precedent for it, amongst the other dialkyl tryptamines.
A structural isomer has been made, with the butyl group branched at the nitrogen atom. This is N-sec-butyl-N-methyltryptamine, or MSBT. It came from a two pass alkylation of N-methyltryptamine (
isopropylalcohol in the presence of solid potassium iodide. It remained an oil, but was over 90% pure by GCMS, with unreacted NMT being the major impurity. MS (in m/z): C6H14N+ 100 (100%); indolemethylene+ 130 (8%); parent ion 230 (1%). It has been assayed in man, but it remains an unknown.
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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