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Book II of PiHKAL: A Chemical Love Story, by Alexander & Ann Shulgin #7: ALEPH-7
#7 ALEPH-7: 2,5-Dimethoxy-4-n-propylthioamphetamine

#7 ALEPH-7 SYNTHESIS: A solution of 2.6 g 2,5-dimethoxy-4-(n-propylthio)benzaldehyde (see under 2C-T-7 for its synthesis) in 20 mL nitroethane and 0.5 g anhydrous ammonium acetate was heated on the steam bath overnight. The excess solvent/reagent was removed under vacuum leaving an orange oil as a residue that cry-stallized spontaneously. This crude product was recrystallized from 20 mL boiling MeOH to give, after cooling, filtering, and air drying, 2.4 g of 1-(2,5-dimethoxy-4-n-propylthiophenyl)-2-nitropropene as orange crystals. Its mp was 83–84 °C with prior sintering at 81 °C.

A suspension of 1.5 g LAH in 150 mL of warm anhydrous THF was stirred under an inert atmosphere and brought up to a gentle reflux. A solution of 2.3 g 1-(2,5-dimethoxy-4-n-propylthiophenyl)-2-nitropropene in 25 mL anhydrous THF was added dropwise at a rate that maintained the reflux. Heating and stirring were continued for 2 days, and then the reaction mixture was allowed to stir at room temperature for an additional 2 days. There was added 1.5 mL H2O (dissolved in 10 mL THF), followed by 1.5 mL 15% NaOH, and finally another 4.5 mL H2O. Stirring was continued until all the curdy solids had turned white. The reaction mixture was filtered, and the filter cake washed with slightly wet THF. The filtrate and the washings were combined, and the solvent removed under vacuum. The residue was about 2 mL of an amber colored oil that was dissolved in 200 mL CH2Cl2. This solution was washed with first dilute NaOH, and then with saturated brine. Removal of the solvent gave a pale amber oil that was dissolved in 10 mL IPA, neutralized with about 14 drops of concentrated HCl, and diluted with 200 mL anhydrous Et2O. The clear solution was decanted from a little gritty material, and then set aside to allow the formation of 2,5-dimethoxy-4-n-propylthioamphetamine hydrochloride (ALEPH-7) as fine white crystals. After filtration and air drying, there was obtained 1.8 g of an off-white powder.

DOSAGE: 4–7 mg.

DURATION: 15–30 h.

QUALITATIVE COMMENTS: (with 4 mg) “At the second hour I had a paraesthetic twinge or two (all pins and needles), and then felt quite relaxed, quite willing to let this play itself out. In the evening my ears still feel ‘popped’ and there is a little bit of physical awareness. There is not much fun with this. The night following, I was unable to sleep and only dozed slightly, but I seemed to be OK the next day.”

(with 6 mg) “The alert was felt within a half hour, and then nothing more. Then, over the next two hours, there was the evolution of an extremely neutral state. I danced wildly to a record of Keith Jarrett, but somehow didn’t care for his style. I fell apart emotionally, with tears and a feeling of total loss of everything. Everything was visible to me only in some strange wide-angle lens viewing. I went for a walk, a waste of time. I tried classical music, but only jazz was acceptable. It was a couple of days before I lost the residual strangeness feeling. Never again.”

(with 7 mg) “I did this alone, and in retrospect I wish I had not. Somewhere between the hours 2 and 3, I got to a full +++, and I was concerned that I saw the effects still developing. Where would it go now? There was no reality loss as with LSD, no shakes or shimmers, but an intense and profound +++ of something characterized only by the absence of extremes. And I am frightened because this is still deepening. A couple of calls to friends were not successful, but I found an ally in the Palo Alto area, and I told him I was coming to visit. My greater than one hour drive there was okay only because I had programmed every move ahead of time. In retrospect, to drive was completely stupid, and I certainly will never do it again, under any circumstances. But, there I was. I knew which lane I would be on, on the S.F. Bay Bridge, at every moment of my travels. The middle lane through the tunnel. The second from the left when descending into San Francisco. The white lane-marker stripes were zipping up past my lateral field of vision as I drove, those that were to my right zipped past my right eye, those to the left past my left eye. Like disturbed fruit flies leaving an over-ripe peach. But, as everything had been preprogrammed, there were no surprises. I made it successfully, and my baby-sitting friend probed, with a blend of curiosity, love, and envy, my uncaring state. And in the course of the next couple of hours, this state evolved into a friendly, familiar place. I was still fully +++, but now for the first time I was at peace with it. A fruit salad tasted heavenly. By midnight I was able to doze lightly, and the next day I was sure that there were some residual effects. The second evening’s sleep repaired everything. The neutralness was something new to me. I don’t like not caring. Was this the “Beth” state of the strange twenty minutes seen by SL in the ALEPH-4 experience?”

(with 7 mg) “Strange, pleasant, unexciting, long-lasting. The induced state was characterized by: clear unintoxicated central field of vision, concentration but with the periphery sensed as being filled with a kind of strangeness, and also something sensed inside, at the back of the head. A feeling of something waiting to erupt, which never does. I had a faint touch of amusement, yet no part of the experience had the depth or richness of other compounds. No tremors. Slight visuals, but only when looked for. Hunger not present, but food tasted fine when eaten. Mildly pleasant but one would not take it again unless bored stiff.”

EXTENSIONS AND COMMENTARY: This drug was the first definition of the term, Beth state.

There is something of the Fournier Transform in any and all drug experiments. A psychedelic drug experience is a complex combination of many signals going all at the same time. Something like the sound of an oboe playing the notes of the A-major scale. There are events that occur in sequence, such as the initial A, followed by B, followed by C-sharp and on and on. That is the chronology of the experience, and it can be written down as a series of perceived phenomena. The notes of the scale. Black quarter notes, with flags at the tops of their staffs, going up the page of music.

But within each of these single events, during the sounding of the note “A,” for example, there is a complex combination of harmonics being produced at the same time, including all components from the fundamental oscillation on up through all harmonics into the inaudible. This mixture defines the played instrument as being an oboe. Each component may be shared by many instruments, but the particular combination is the unique signature of the oboe.

This analogy applies precisely to the study of psychedelic drugs and their actions. Each drug has a chronology of effect, like the notes of the A-major scale. But there are many components of a drug’s action, like the harmonics from the fundamental to the inaudible which, taken in concert, defines the drug. With musical instruments, these components can be shown as sine waves on an oscilloscope. One component, 22%, was a sine wave at a frequency of 1205 cycles, and a phase angle of +55°. But in psychopharmacology? There is no psychic oscilloscope. There are no easily defined and measured harmonics or phase angles. Certainly, any eventual definition of a drug will require some such dissection into components each of which makes some contribution to the complex whole. The mental process may some day be defined by a particular combination of these components. And one of them is this Beth state. It is a state of uncaring, of anhedonia, and of emotionlessness.

Many drugs have a touch of this Beth state, ALEPH-7 more than most. If a sufficient alphabet of effects (I am using the Alephs, Beths, Gimels, and Daleths of the Hebrew as token starters only) were to be accumulated and defined, the actions of new materials might someday be more exactly documented. Could depression, euphoria, and disinhibition for example, all be eventually seen as being made up of their component parts, each contributing in some measured way to the sum, to the human experience? The psychologists of the world would be ecstatic. And drugs such as ALEPH-7 might be useful in helping to define one of these parts.

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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