Tryptamine, 4-hydroxy-N,N-tetramethylene · 4-Indolol, 3-[2-(1-pyrrolidyl)ethyl] · Pyrrolidine, 1-[2-[3-(4-hydroxy)indolyl]ethyl] · 4-Hydroxy-N,N-tetramethylenetryptamine · 3-[2-(1-Pyrrolidyl)ethyl]-4-indolol · 1-[2-[3-(4-Hydroxy)indolyl]ethyl]pyrrolidine · “4-Hydroxypyrrolidyltryptamine” · “4-Hydroxypyrrolidylindole
#24 4-HO-pyr-T SYNTHESIS: A solution of 0.50 g 4-acetoxyindole (see under for its preparation) in 5 mL Et2O was stirred and cooled to 0 °C with protection from atmospheric moisture. There was then added 0.5 mL oxalyl chloride. The reaction mixture was stirred for an additional 30 min, and the intermediate indoleglyoxyl chloride separated as a yellow crystalline solid but was not purified. This was treated with a 40% solution of pyrrolidine in anhydrous Et2O, dropwise, until the pH was 8–9. The reaction was diluted with 100 mL CHCl3 and shaken with 30 mL of a 5% aqueous NaHSO4 followed by 30 mL of a saturated aqueous NaHCO3 solution. After drying over anhydrous MgSO4, the organic solvents were removed under vacuum. The residue was recrystallized from CHCl3/hexane to give 0.47 g (55%) of 4-acetoxyindol-3-yl-N,N-tetramethyleneglyoxylamide with a mp 174–176 °C. Anal: C,H,N.
To a stirred suspension of 0.25 g LAH in 10 mL anhydrous THF, under nitrogen and at room temperature, there was added a solution of 0.30 g 4-acetoxyindol-3-yl-N,N-tetramethyleneglyoxylamide in 10 mL anhydrous THF. This was added dropwise at a rate that maintained the reaction at reflux. When the addition was complete, the reflux was maintained for an additional 15 min and then the reaction was cooled to 40 °C. The excess hydride and the product complex were destroyed by the addition of 0.5 mL EtOAc followed by 1.5 mL H2O. The solids were removed by filtration, the filter cake washed with THF, the filtrate and washings pooled, and the solvents removed under vacuum. The residue was recrystallized from EtOAc/hexane to give 0.12 g (50%) of 4-Hydroxy-N,N-tetramethylenetryptamine (4-HO-pyr-T) with a mp 193–195 °C. Anal: C,H,N.
DOSAGE: >20 mg
DURATION: unknown
QUALITATIVE COMMENTS: (with 20 mg, orally) “This substance proved to be quite unlike and bordered on the bizarre. There was a latency period of about three hours after ingestion before the onset was noted. Visual disturbances were minimal; no alteration in colors or objects occurred. The nature of this compound was characterized by the heightening of the intellectual process, but not to the extent seen with . The entire experience was more ‘stimulant-like’ rather than hallucinogenic. A very unpleasant ride. Have no desire to go deeper or, indeed, to look at the other cyclic analogs.”
EXTENSIONS AND COMMENTARY: There are three pyrrolidine amines in this tryptamine compilation, and all three are simply weird and illogical. Both the simple “pyrrolidyl tryptamine” () and the 5-methoxy counterpart () caused physical distress, and this one (4-HO-pyr-T) seems to be a more of a stimulant rather than a psychedelic. In all three cases (and with the 5,6-methylenedioxy example as well) the other two ring systems that often accompany the pyrrolide example as a “set” were simply not explored. This is due, largely, to the unexpected and generally negative responses to the pyrrolidine archetype. The piperidine homologue () is a white crystalline solid with a mp of 180–181 °C. The morpholine analogue () is also a white crystalline solid with a mp of 177–178 °C.
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,
Box 13675
Berkeley, CA 94701

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