Book II of PiHKAL: A Chemical Love Story. Alexander & Ann Shulgin #5: ALEPH-4
#5 ALEPH-4 SYNTHESIS: A solution of 2.0 g 2,5-dimethoxy-4-(isopropylthio)benzaldehyde (see under for its synthesis) in 12 mL nitroethane was treated with 0.4 g anhydrous ammonium acetate and heated on the steam bath for 12 h, then allowed to stir for another 12 h at room temperature. The excess solvent/reagent was removed under vacuum leaving a residue as a heavy deep orange two-phase oily mass. This was brought into one phase with 2 mL MeOH and then, with continued stirring, everything spontaneously crystallized. This product was removed by filtration and, after washing sparingly with cold MeOH and air drying, yielded 2.0 g of 1-(2,5-dimethoxy-4-isopropylthiophenyl)-2-nitropropene as orange crystals with a mp of 96–98 °C. After recrystallization from 15 mL boiling 95% EtOH, filtering and air drying to constant weight, there was obtained 1.6 g of orange crystals with a mp of 99–100 °C.
A suspension of 1.0 g LAH in 100 mL warm THF was stirred under a N2 atmosphere and heated to a gentle reflux. To this there was added, dropwise, a solution of 1.2 g 1-(2,5-dimethoxy-4-isopropylthiophenyl)-2-nitropropene in 20 mL anhydrous THF. This mixture was held at reflux for 1 day, then stirred at room temperature for 2 days. There was then added, slowly and with caution, 1 mL of H2O, followed by 1 mL of 15% NaOH, and finally by another 3 mL of H2O. Stirring was continued until the reaction mixture became white and granular, then all solids were removed by filtration and the filter cake was washed with additional THF. The filtrate and washings were combined, and the solvent removed under vacuum to give 1.1 g of residue which was an almost white oil. This was dissolved in 6 mL IPA, neutralized with concentrated HCl (10 drops were required) and then diluted with 200 mL anhydrous Et2O. The resulting slightly turbid solution was clarified by filtration through a sintered glass filter, and the clear and slightly yellow filtrate was allowed to stand. A fine white crystalline product slowly separated over the next few h. This product, 2,5-dimethoxy-4-isopropylthioamphetamine hydrochloride (ALEPH-4) was removed by filtration, and after washing with Et2O and air drying, weighed 0.5 g and had a mp of 146–147 °C, with prior sintering at 144 °C.
DOSAGE: 7–12 mg.
DURATION: 12–20 h
QUALITATIVE COMMENTS: (with 7 mg) “Things started off going downhill, initially negative with tension and depression, but as the momentum developed, so did the positive effect. My discomfort continued to develop, but I was struck by the visual beauty of the trees and the small stream that flowed off the mountain. My experience continued to grow, simultaneously, in both the negative and the positive direction. Physically I was uncomfortable and found my breathing difficult, but I acknowledged a rapture in the very act of breathing. All moved over to the plus side with time, and the evening was gorgeous. I have never seen the sky so beautiful. The only flaw was when I choked on some lemonade and it seemed to me I almost drowned. I have been extremely conscious of eating, drinking and swallowing ever since. I barely slept the whole night and awoke extremely tired. I felt that the experience continued for many days, and I feel that it is one of the most profound and deep learning experiences I have had. I will try it again, but will block out more time for it.”
(with 8 mg) “There was without question a plus two, but none of the edges of unreality that are part of . The sounds that are just outside of my hearing are intriguing, and distract me from the eyes-closed imagery that is just barely possible with music while lying down. But, going outside, there were no obvious sources of the sounds that I heard. Could I drive? I suspect so. I took a shower and did just that—I drove to San Francisco without incident, and walked amongst the many strange faces on the downtown streets.”
(with 12 mg) “The experience was very intense but completely under control except for a twenty minute period right in the middle of it. I had to get away from everything, from everyone. There was a sense of being surrounded and moved in upon that was suffocating. I was weighed down with everything—physical, psychic, emotional. My clothes had to come off, my hair had to be released, my shoes went, I needed to move away from where I was, to somewhere else, to some new place, any new place, with the hope that my other old place wouldn’t follow me. Pretty soon I found I was myself, I could breathe again, and I was OK. Rather sheepishly, I dressed and rejoined the group. The rest of the day was spectacular, but those few minutes were scary. What if I couldn’t have escaped?”
EXTENSIONS AND COMMENTARY: Again, there are hints and suggestions of complexities. These, and several other reports, suggest some sensory confusion, and interpretive aspects that are to some extent threatening. There is an underlying suggestion of body toxicity. I know of no experiment that exceeded 12 milligrams and I would not be able to predict what might come forth at higher dosages. I personally choose not to try them.
16 December 2015 · Creative Commons BY-NC-SA ·

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. Many, many others have since been added.
I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore the typographic niceties found in the printed edition. I’ve also 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 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.
Though 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.
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