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Book II of PiHKAL: A Chemical Love Story, by Alexander & Ann Shulgin #89: HOT-17
#89 HOT-17: 2,5-Dimethoxy-4-sec-butylthio-N-hydroxyphenethylamine

#89 HOT-17 SYNTHESIS: To a well-stirred solution of 6.08 g 2,5-dimethoxy-4-sec-butylthio-β-nitrostyrene (see under 2C-T-17 for its preparation) in 80 mL anhydrous THF under a He atmosphere, there was added 3.5 mL 10 M borane dimethylsulfide complex, followed by 0.5 g of sodium borohydride. As the stirring continued, the slightly exothermic reaction slowly faded from bright yellow to pale yellow, and eventually (after three days stirring) it was substantially colorless. There was then added 80 mL of 3 N HCl and the mixture heated on the steam bath for 1 h, and then allowed to return to room temperature. An additional 600 mL H2O was added (there was a combination of crystals and globby chunks in the aqueous phase) and this was then extracted with 3×75 mL CH2Cl2. The color went completely into the organic phase. This was washed with 2×50 mL aqueous K2CO3, yielding a rusty-red colored CH2Cl2 solution, which on removal of the solvent, yielded 4.5 g of a red oil. A side effort to make the sulfate salt at this stage with H2O and a little H2SO4, indeed gave solids, but all of the color remained in the sulfate salt. The red oil was dissolved in 45 mL IPA and neutralized with concentrated HCl to bright red, not yellow, on universal pH paper. The addition of 350 mL anhydrous Et2O instituted the slow precipitation of white crystals. After filtering and air drying, there was obtained 1.32 g 2,5-dimethoxy-4-sec-butylthio-N-hydroxyphenethylamine hydrochloride (HOT-17). The aqueous phase from above was just neutralized with 25% NaOH (cloudy, slightly pink color) and then made basic with K2CO3 (the color becomes green). This was extracted with 3×75 mL CH2Cl2, the extracts pooled, and the solvent removed to yield 0.5 g of a white oil. This was dissolved in 5 mL IPA, neutralized with concentrated HCl, and diluted with a equal volume of Et2O. An additional 0.36 g of product was thus obtained.

DOSAGE: 70–120 mg.

DURATION: 12–18 h.

QUALITATIVE COMMENTS: (with 70 mg) “There was a light feeling, a little off-the-ground feeling, which made walking about a most pleasant experience. No distortion of the senses. And there was no sense of the beginning of a drop of any kind until about the eighth hour. Sleeping was a bit tricky but it worked out OK (at the twelfth hour of the experience). A completely valid ++.”

(with 120 mg) “HOT-17 has an unbelievably grim taste—not bitter, but simply evil. There is a steady and inexorable climb for three hours to a sound and rolling plus three. There was absolutely no body difficulty, but there was still something going on upstairs well into the next day. Writing was surprisingly easy; I was completely content with the day, and would be interested in exploring it under a variety of circumstances.”

(with 120 mg) “This is my first time with this material. It is 4:45 p.m. Small nudge at 30 minutes, but not too real. At one hour, threshold, quite real. 6:15 to a +1. By 7:25, +3 about. 7:45, no doubt +3. Possibly still climbing; I hope so. No body discomfort at all, no apparent body push. This aspect of it is similar to the easy body of the HOT-2. However, it’s at times like these that I reflect on just exactly how hard-headed we two are. I mean, +3 is no longer the out-of-body, nearly loss of center state it used to be, four years ago. The question intrudes: would a novice experience this as a very scary, ego-disintegrating kind of experiment, or not? Silly question which answers itself. Yes, of course. At 3 hours, aware of some mild time-distortion. More a tendency to not think in terms of clock-time, than actual distortion. The mind lazy when attempting to keep track of clock time. Feel it would be quite easy and pleasant to continue writing. The energy could very well go in that direction. However, the idea of the erotic is also quite agreeable. This is, so far, a good-humored Buddha area of the self.”

EXTENSIONS AND COMMENTARY: Two virtues sought by some users of psychedelic drugs are high intensity and brief action. They want a quicky. Something that is really effective for a short period of time, then lets you quickly return to baseline, and presumably back to the real world out there.

Intensity is often (but not always) regulated by dose. The pharmacological property of dose-dependency applies to many of these drugs, in that the more you take, the more you get. If you want more intensity, take a second pill. And often, you get a longer duration as an added property. But it is instructive to inquire into the rationale that promotes brevity as a virtue. I believe that it says something concerning the reasons for using a psychedelic drug. A trade off between learning and entertainment. Or between the achieving of something and the appearance of achieving something. Or, in the concepts of the classics, between substance and image.

In a word, many people truly believe that they cannot afford the time or energy required for a deep search into themselves. One has to make a living, one has to maintain a social life, one has a multitude of obligations that truly consume the oh-so-few hours in the day. I simply cannot afford to take a day off just to indulge myself in such-and-such (choose one: digging to the bottom of a complex concept, giving my energies to those whom I can help, to search out my inner strengths and weaknesses) so instead I shall simply do such-and-such (choose one: read the book review, go to church on Sunday morning, use a short-acting psychedelic). The world is too much with us. This may be a bit harsh, but there is some merit to it.

HOT-17 is by no means a particularly potent compound. The hundred milligram area actually has been the kiss of death to several materials, as it is often at these levels that some physical concerns become evident. And it certainly is not a short lived compound. But, as has been so often the case, the long lived materials have proven to be the most memorable, in that once the entertainment aspect of the experience is past you, there is time for dipping deeply into the rich areas of the thought process, and the working through of ideas and concepts that are easily available. And when this access is coupled to the capability of talking and writing, then a rewarding experience is often the result.

As with the parent compound, 2C-T-17 itself, the presence of an asymmetric carbon atom out there on the sec-butyl side chain will allow the separation of HOT-17 into two components which will be different and distinct in their actions. The activity of the racemic mixture often is an amalgamation of both sets of properties, and the separate assay of each component can often result in a fascinating and unexpected fractionation of these properties.

Page updated 30 March 2012 · This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License ·

About PiHKAL • info

This version of Book II of PiHKAL is based on the Erowid online version, originally transcribed by Simson Garfinkle and converted into HTML by Lamont Granquist. I drew also on “Tyrone Slothrop’s” (Unfinished) Review of PIHKAL to enumerate the many analogues mentioned in PiHKAL but not described at length. Still others remain to be added.

I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore most of the typographic niceties found in the printed edition. I’ve also made minor changes to some chemical names in line with current nomenclature practice, and in the hope of aligning with more readers’ searches. Typically the change is little more than expanding a prefix and setting it in italics. The errata and changes 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 PiHKAL has been reserved in all forms and it may not be distributed. Book II of PiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.

Ordering Information

PiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of phenethylamines. This book belongs in the library of anyone seeking a rational, enlightened and candid perspective on psychedelic drugs.

Although Sasha and Ann have put Book II of PiHKAL 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.

PiHKAL (ISBN 0-9630096-0-5) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.

Transform Press,
Box 13675
Berkeley, CA 94701

510 · 934 · 4930 (voice)
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