Tryptamine, N,N-tetramethylene · Indole, 3-[2-(1-pyrrolidyl)ethyl] · Pyrrolidine, 1-[2-(3-indolyl)ethyl] · N,N-Tetramethylenetryptamine · 1-[2-(1H-Indol-3-yl)ethyl]pyrrolidine · 1-[2-(1-Pyrrolidyl)ethyl]indole · “Pyrrolidyltryptamine”
#52 pyr-T SYNTHESIS: To a well-stirred solution of 1.0 g indole in 15 mL TBME there was added, dropwise over the course of 20 min, a solution of 1.1 g oxalyl chloride in 15 mL TBME. Yellow crystals of indol-3-ylglyoxyl chloride appeared at about the half-addition point. Stirring was continued for an additional 10 min. This intermediate was removed by filtration, washed sparingly with TBME, and used directly in the following step. The above indol-3-ylglyoxyl chloride was added, a bit at a time, to 2.1 mL anhydrous pyrrolidine that was being vigorously stirred. The color was discharged, and reaction mixture became a pale, almost colorless. To this product there was added 80 mL of 1 N HCl, the mixture cooled, and the resulting solids removed by filtration, washed with H2O and air-dried. This was recrystallized from 30 mL boiling CH3CN (slow to dissolve, slow to crystallize out) to give, after filtration, CH3CN washing, and air drying, 0.87 g (42%) of indol-3-yl-N,N-tetramethyleneglyoxylamide with a mp of 219–220 °C. The literature reports a mp 224–225 °C. IR (in cm-1): 753, 789, 834, 1143, 1161,1181, C=O 1615 (br), NH at 3150.
A solution of 0.76 g indol-3-yl-N,N-tetramethyleneglyoxylamide in 15 mL anhydrous dioxane was added, slowly, to 0.8 g LAH in 15 mL dioxane which was well-stirred and held at reflux temperature under an inert atmosphere. After the addition was complete, reflux 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 distilled at the KugelRohr at 0.05 mm/Hg yielding a fraction boiling at 170–180 °C which spontaneously crystallized. Thus, there was obtained 0.35 g (52%) of N,N-Tetramethylenetryptamine with a mp 114–115. IR (cm-1): 740, 784, 807, 886, 1011, 1108. MS (in m/z): C5H10N+ 84 (100%); indolemethylene+ 130 (7%); parent ion 214 (3%). A solution of this base in Et2O treated with anhydrous HCl gave the hydrochloride salt which, on recrystallization from MeOH/benzene, had a mp 193–194 °C.
DOSAGE: unknown
DURATION: unknown
QUALITATIVE COMMENTS: (with 25 mg, orally) “There was a general malaise without any particular spiritual or noble side to it. I was sick.”
(with 50 mg, orally) “There is maybe something here, but it is unpleasant. Salivation, muscle and joint pains. I tried smoking it earlier and it was almost inactive. Certainly less potent than or .”
(with 70 mg, smoked) “This smells like a mixture of and naphthalene. The effects began very soon and lead to an intense, but a little bit uncomfortable, high. I was distinctly dizzy, and the visuals were minor. I would classify this compound in the ‘not too pleasant’ category, certainly not colorful.”
EXTENSIONS AND COMMENTARY: First of all, the name pyr-T, which is an abbreviation for “pyrrolidinyltrypamine” is out-and-out wrong. There is just one single nitrogen at the end of the tryptamine chain and it cannot be claimed by both halves of the name. It is intrinsic to the name pyrrolidine as well as to the name tryptamine. This is why the name is in quotation marks. This drug has occasionally been called PT in the popular literature, but the choosing to spell it out as pyr-T allows a parallel code to be used with the piperidine and morpholine analogues. These two analogues are both described in the literature. The piperidine material, , is made via the glyoxylamide (mp 182–183 °C) which is reduced with LAH to the target amine (mp 149–150 °C, HCl salt 220–221 °C). The morpholine analogue also came to be via the glyoxylamide (mp 187–188 °C) and the reduction to the amine which can be an oil, but which has been reported to have a mp 145–147 °C. The only trials I know of with either of these is with which, as the fumarate salt, had no effects at all upon the i.m. injection of a 30 milligram bolus.
Actually, this neat trilogy of heterocyclics, the pyrrolidine ring, the piperidine ring, and the morpholine ring, have been the chemists favorite for many years. Leaf through the “Known Tryptamines” appendix, and see how often you see stretched between the nitrogen substituents the phrases:
  • —C C C C—
  • —C C C C C—
  • —C C O C C—
These are the exact rings. They are easy to make; they add a sense of sophistication to an otherwise pedestrian scientific paper; and they often represent the inactive extremes in a receptor site study of a structure activity relationship study of a CNS-active agent. But the compounds represented here appear to have simply the wrong properties, somehow, and should not really be seriously considered in the quest for understanding of the remarkable actions of most of the psychedelic phenethylamines and tryptamines.
And yet no observation, favorable or unfavorable, deserves to be discarded. The very failure to act in an expected way might, if completely understood, add to our intimate understanding of the mystery of why these materials do what they do.
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.
Transform Press,
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