Tryptamine, 5-methoxy-N,N-tetramethylene · Indole, 5-methoxy-3-[2-(1-pyrrolidyl)ethyl] · Pyrrolidine, 1-[2-(5-methoxy-1H-indol-3-yl)ethyl] · 5-Methoxy-N,N-tetramethylenetryptamine · 5-Methoxy-3-[2-(1-pyrrolidyl)ethyl]indole · 1-[2-(5-Methoxy-1H-indol-3-yl)ethyl]pyrrolidine · “5-Methoxypyrrolidyltryptamine”
#43 5-MeO-pyr-T SYNTHESIS: To a well-stirred solution of 1.25 g 5-methoxyindole in 15 mL TBME there was added dropwise a solution of 1.1 g oxalyl chloride in 15 mL TBME, over the course of 20 min. Stirring was continued for an additional 10 min during which time there was the separation of 5-methoxyindol-3-ylglyoxyl chloride as a tomato-red crystal, which was removed by filtration and washed with a small amount of TBME. The loose crystals were added, a bit at a time, to 2.0 mL well-stirred pyrrolidine, and the stirring continued until the red color had dissipated and the solids had returned to room temperature as a cream-colored paste. There was then added 80 mL of 1 N HCl which produced a product with a loose crystalline texture. This was removed by filtration yielding, after air drying at 100 °C to constant weight, 1.13 g of a cream colored material with a mp in the 180–195 °C area. Recrystallized from 15 mL of boiling MeOH gave, after cooling and filtering, 5-methoxyindol-3-yl-N,N-tetramethyleneglyoxylamide as a white crystalline solid weighing, after air-drying to constant weight, 0.65 g (28%) with a mp of 211–212 °C. IR (in cm-1): 700, 741, 792, 1013, 1150, 1188, with a broad carbonyl centered at about 1620 and the indolic NH stretch seen as a broad peak at 3160.
A solution of 0.52 g 5-methoxyindol-3-yl-N,N-tetramethyleneglyoxylamide in 15 mL anhydrous dioxane was added, slowly, to 0.80 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 pale amber residue was distilled at the KugelRohr at 160–170 °C at 0.05 mm/Hg to give 0.11 g (23%) of 5-methoxy-N,N-tetramethylenetryptamine as an off-white oil that did not crystallize. MS (in m/z): C5H10N+ 84 (100%); methoxyindolemethylene+ 160 (4%); parent ion 244 (6%). The hydrochloride salt was prepared by treating an Et2O solution of the free base with anhydrous hydrogen chloride gas, and recrystallizing the formed solids from MeOH/benzene. The mp was 164–167 °C.
DOSAGE: 0.5–2 mg, orally; 2–3 mg smoked
DURATION: several hours
QUALITATIVE COMMENTS: (with 0.5 mg, orally) “This stuff is an absolute poison. Within minutes I noticed what can only be called ear-ringing without any ear-ringing. Intense tinnitus with no sound, most uncomfortable. There were two waves of nausea and vomiting of yellow bilious stuff, with thick mucus for saliva. I can’t think straight—muddled. I can’t get answers to questions because I simply cannot form the questions. Eyes closed to music gave no images, but the music sounded OK. Recovery was quite rapid, and I was together again in a few hours. Never again.”
(about 1 mg, smoking) “I managed to vaporize about a milligram of the material, and there was nothing profound. There was a slight feeling of calmness. As I felt sure that this material would be a quieting agent, I managed to vaporize and inhale what might have been up to another milligram. There were no psychedelic effects manifested, and I fell asleep easily 10 minutes later.”
(with 3 mgs, smoking) “Initially the compound exhibited a -like effect. There was a total loss of self-identity in a nearly instantaneous rush. I felt as if the top of my head was blown off at the inset onset of the drug experience. My observers told me that I had been unconscious for four hours. I remember reentering with the feeling ‘God is Love.’ After completely coming to, I felt very nauseous, and threw up in the bathroom several times. I felt drained and sick for the rest of the evening as well as mentally slow. By the next morning I was more alert and responsive, I have absolutely no memory of anything that transpired while I was on the compound.”
(with 3 mgs, smoking) “I inhaled the vaporized sample at 10 past noon. There was quite a rush. There were none of the shifting shapes, colors and forms of . Nor was it acute with clarity or energy as with my many experiences with . The effect was intense but not terrifying, with a full body buzz and with humming resonance as I fell backwards into something where all memory was lost. I was told that at 18 past noon, I was unconscious. Something over an hour later, I started flailing, rolling about, quivering and shaking, and had very constricted pupils. In another hour I was able to talk lucidly, but quietly. In yet another hour, I was nauseous and tried for the bathroom, but didn’t make it. The people who were watching me were alarmed. My actions were scary. And my skin looked funny for several days afterwards. There are long-lasting properties of this. My first exposure was with perhaps a milligrams (smoked, also) and the effects were substantial, with rough edges and minor dysphoria.”
(with 4 mgs, smoking) “This was the free base. I remember the pipe, and the inhalation and, with the pouring of a small glass of scotch, I settled down in front of the TV to watch a re-run of Star Trek. That was it. I came to some time later in the front room of a professional ally of mine, who had by chance discovered me walking down the street near his house. I do not recall, nor have I been able to regain any memories of the time I was ‘out there.’ I apparently experienced no physical discomfort from the drug. In fact I distinctly remember feeling very comfortable when I awoke. Clearly this compound is some weird-ass shit.”
EXTENSIONS AND COMMENTARY: Again, as with other compounds in these writings, there is an irresistible urge to present generalizations. But with this particular material, there are obvious unresolved problems with both dosage or duration, as such I am limited to the few comments provided above. Dosage? A very few milligrams parenterally, but with smoking such small amounts it is hard to accurately estimate the actual dosages received. Duration? One subject could be fine the next morning, and another could be still aware of wrongness a week later. I am uncomfortable with any compound that seems to be widely variable in its impact on different people.
The qualitative aspects of these (and other) reports imply some individual variability. It is always easy to look at tryptamines such as this one, or the others in these recipes, and say, “We know that they are psychedelics. And maybe good ones or maybe bad ones. So we should look at them with that preconceived notion in mind.” But looking objectively at this particular compound, 5-MeO-pyr-T, we are far away from any vocabulary of psychedelics. How is it different from, say, what one might expect from a Fentanyl analogue? Here is a collection of trials that describe parenteral administration, and the quick development of an anesthesia. This compound may not be the new Fentanyl because of the nausea during what would be the recovery period. But what are the chances that, perhaps not with this compound, but with any of the obvious analogues that are screaming to be assayed, there just might be a useful clinical tool?
There is another message of warning. Here one must accept the eloquent argument that, for the structuring of an experiment with an unknown and thus undefined new drug, there must be observers present who are both sober and sympathetic. The heroic and macho, “I’ll do it my way,” can lead to both psychological problems and physical risks. As with scuba diving, always work with a partner.
With both and , there are two additional ring analogies that are natural companions to 5-MeO-pyr-T. These are the piperidine and the morpholine counterparts, and . Both compounds are in the literature, and an entry reference to them can be gotten from the “known tryptamines” appendix. Along with the pyrrolidine material I had made a reasonable supply of the amides for these other two, both by way of the 5-methoxyindole and oxalyl chloride procedure given above. With piperidine, there is 5-methoxyindol-3-yl-N,N-pentamethyleneglyoxylamide, mp 167–169 °C and IR, (in cm-1), 730, 780, 811, 928, 1033, 1161, a broad carbonyl at 1600 and a broad indolic NH stretch at 3190. With morpholine, the corresponding glyoxylamide melted at 193–194 °C, with an IR spectrum (in cm-1), of 747, 791, 856, 925, 976, 1043 and 1122, the carbonyl at 1620 and the broad NH at 3150.
With the rather unexpected, and unencouraging descriptions of the pyrrolidine tryptamines in general, and this one in particular, I was not too blinding a hurry to explore the two heterocyclic analogues. The amides are still on the shelf in the lab. If some good reason comes forth to assay the final amines, they can be made with a dash of lithium aluminum hydride, but until then I have other things to 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.
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