SYNTHESIS: A well-stirred solution of 1.77 g 2,5-dimethoxy-β-nitro-4-(n-propylthio)styrene (see under 2C-T-7 for its preparation) in 20 mL anhydrous THF was placed in an He atmosphere and treated with 1.5 mL of 10 M borane-dimethyl sulfide complex. This was followed by the addition of 0.2 g sodium borohydride, and the stirring was continued at room temperature for a week. The volatiles were removed under vacuum, and the residue was treated with 20 mL dilute HCl and heated on the steam bath for 30 min. The cooled yellow solution set up as solids. The addition of H2O was followed by sufficient K2CO3 to make the aqueous phase basic. All efforts to work with an acidified aqueous phase resulted in terrible emulsions. The basic phase was extracted with 3×75 mL CH2Cl2, and the pooled extracts washed with H2O, then stripped of solvent under vacuum. The residual yellow oil was dissolved in 20 mL IPA, neutralized with 15 drops of concentrated HCl, and then diluted with 50 mL anhydrous Et2O. After a few minutes stirring, a white crystalline solid separated. This was removed by filtration, washed with Et2O, and air dried to constant weight to provide 0.83 g of 2,5-dimethoxy-N-hydroxy-4-n-propylthiophenethylamine hydrochloride (HOT-7).
DOSAGE: 15–25 mg.
DURATION: 6–8 h.
QUALITATIVE COMMENTS: (with 15 mg) “I am lightheaded, and maybe a little tipsy. I am well centered, but I don’t want to go outside and meet people. Shades of alcohol woozy. The effects were going already by the fifth hour and were gone by the seventh hour. I would call it smoothly stoning.”
(with 22 mg) “The transition into the effects was a bit difficult, with a faint awareness in the tummy. But by the second hour it was quite psychedelic, and the body was not thought of again, except in terms of sexual fooling around. Very rich in eyes-closed imagery, and very good for interpretive and conceptual thinking. But the eyes-open visuals were not as much as they might have been. At the seventh hour, drifted into an easy sleep.”
(with 22 mg) “The experience was very positive, but at each turn there seemed to be a bit of sadness. Was it a complete plus three experience? Not quite. But it didn’t miss by much. The erotic explorations somehow just failed to knit by the thinnest of margins. It was a truly almost-magnificent experience.”
EXTENSIONS AND COMMENTARY: There is a working hypothesis that has been growing in substance over the last few years in this strange and marvelous area of psychedelic drugs. It all was an outgrowth of the rather remarkable coincidence that I had mentioned in the discussion that followed MDOH. There, an assay of what was thought to be MDOH gave a measure of activity that was substantially identical to MDA, and it was later found out that the material had decomposed to form MDA. So, MDA was in essence rediscovered. But when the true, valid, and undecomposed sample of MDOH was actually in hand, and assayed in its own rights, it was found to have a potency that really was the same as MDA. So, the working hypothesis goes something like this:
An N-hydroxy amine has approximately the same potency and the same action as its N-hydrogen counterpart.
Maybe the N-hydroxy compound reduces to the N-H material in the body, and the latter is the intrinsically active agent. Maybe the N-H material oxidizes to the N-hydroxy material in the body, and the latter is the intrinsically active agent. Either direction is reasonable, and there is precedent for each. The equivalence of MDA and MDOH was the first suggestion of this. And I have made a number of NH vs. NOH challenges of this hypothesis. The interesting 2C-T-X series has provided a number of amines that are amenable to N-hydroxylation, and this is the first of them. And, after all, if you put a hydroxy (HO) group on a thio material (T), you have a HOT compound.
So, as far as nomenclature is concerned, the family of N-hydroxy analogues of N-H amines is known as the HOT family.
How does HOT-7 compare with 2C-T-7? They are almost identical. The same range of dose (centering on 20 milligrams) and if anything, perhaps slightly less long lived. Lets try some other N-hydroxys!
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.
“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
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.
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,