Tryptamine, N,N-Diallyl · N,N-Diallyltryptamine · Indole, 3-[2-(Diallylamino)ethyl] · 3-[2-(Diallylamino)ethyl]indole
SYNTHESIS: To a solution of 1.60 g. tryptamine (10 mM) in 25 mL tetrahydrofuran, there was added 5.2 mL diisopropylethylamine and 2.72 mL allyl iodide (30 mM). The solution (which became cloudy in 20 minutes) was stirred at ambient temperature for 12 hrs. The dark red solids that formed were broken up mechanically and, after they had settled, the overhead liquid was removed by decantation. The remaining solids were washed with 30 mL anhydrous ether, and these washings were combined with the decanting and the volatiles were removed on the rotary evaporator. The crude isolate was dissolved in 1.0 mL pyridine and treated with 1.0 mL acetic anhydride, heated on the steam bath for 0.5 h., diluted with 40 mL 0.5 N. aq. HCl and washed with three 25 mL portions of methylene chloride. The aqueous fraction was made basic with 5% aq. NaOH, extrtacted with three 25 mL portions of methylene chloride which were combined and the solvent removed on the rotary evaporator. The residue (0.68 g.) was distilled at the KugelRohr (b.p. 155–165 C., 40 microns) to yield 0.21 g. of a nearly colorless oil that spontaneously crystallized in the receiver. This was dissolved in 2.0 mL isopropanol, treated with conc. HCl dropwise until the solution was acidic to external damp pH paper (about seven drops required) and diluted with 10 mL anhydrous ether which produced, with scratching, fine powdery crystals. These were removed by filtration, washed with ether, and allowed to air-dry to constant weight. There was thus obtained 0.174 g of the first crop of N,N-diallyltryptamine hydrochloride (DALT). GCMS indicated a purity of >99%, and fragmenets (m/z): 110 (diallylaminomethylene fragment 100%), 130 (3-indolemethylene fragment, 15%), 199 (1%) and 240 (parent, 1%). The infra-red spectrum contained the following major peaks (cm-1): 750, 767, 801, 940, 952 and 1106. The m.p. was 142–143 C.
The solids that remained following the above decantations were thoroughly titurated under 25 mL methylene chloride and the remaining white powder removed by filtration, washed generously with methylene chloride and air-dried to constant weight. The white solid weight (3.74 g.) had an infra-red spectrum consistent with the quatenary salt N,N,N-triallyltryptammonium iodide (cm-1): 753, 950, 980, 991, 1011, 1090, 1100. LCMS indicated a cation with a molecular weight of 281. Removal of the solvent from the mother liquors provided 5.10 g. of a yellow-tan solid that had an infra-red spectrum identical to that of a reference sample of diisopropylethylamine hydriodide.
To a solution of 1.1 g. phenylmercaptan (10 mM) in 20 mL acetone, there was added 0.4 g. 50% W/W NaOH (5 mM) followed by 2.04 g. of N,N,N-triallyltryptammonium iodide (5 mM) and the mixture held at reflux on a steam bath for 12 hr. After removal of all volatiles on the rotary evaporator, the residue was suspended in 75 mL water and made acidic with the addition of aq. HCl. This was washed with 2×40 mL methyene chloride (the washings were saved), made basic with 5% NaOH, and extracted with 3×40 mL methylene chloride. The combined extracts were stripped of solvent on the rotary evaporator yielding 0.354 g. of a pale yellow oil which crystallized. Distillation at the KugelRohr yielded 0.13 g of a white oil which as converted to the DALT hydrochloride salt (as above) weighing 0.10 g. The methylene chloride washings above, on removal of the solvent, yielded a small amount of a brown oil (additional diallyltryptamine) and a clear colorless fluid that set to a spectacular crystalline mass of diphenyldisulfide.
DOSAGE: >40 milligrams, orally
EXTENSIONS AND COMMENTARY: As far as I can determine, there has only been a single human trial of DALT mentioned in the published clinical literature. This was by Dr. Stephen Szara long ago, in 1960 plus or minus a year or two. Most of the literature papers that make reference to N,N-diallyltryptamine are reviews of the structure-activity relationships of the psychedelics, and thus they do not present any new human data. It is an interesting trip to work backwards from these reviews to the original statements that were made.
Most listed potencies are based on the generalization that the activity of DALT was similar to that of
So, the early and only discovery report of DALT mentioned neither the synthetic preparation, the dosage taken, the route of administration, nor the effects observed. It merely stated that the activity had been found. I have explored it up to 42 milligrams, I was to a +1 in an hour, back to baseline at the fourth hour, and there was nothing that caught my fancy.
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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