Book II of PiHKAL: A Chemical Love Story. Alexander & Ann Shulgin #82: G-3
#82 G-3 SYNTHESIS: A solution of 3.7 g of 2,5-dimethoxy-3,4-(trimethylene)benzaldehyde (see preparation under ) in 15 mL nitroethane was treated with 0.7 g anhydrous ammonium acetate and heated on the steam bath for 2.5 h. The excess solvent was removed under vacuum leaving some 5 mL of a deep orange-red oil which on cooling, spontaneously crystallized. This was finely ground under 10 mL MeOH, filtered, washed sparingly with MeOH, and air dried to give 3.6 g of orange crystals with a strong smell of old acetamide. The mp was 92–93 °C. All was recrystallized from 30 mL boiling MeOH to give, after filtering and drying, 2.9 g of 1-(2,5-dimethoxy-3,4-(trimethylene)phenyl)-2-nitropropene as yellow crystals with a mp of 93–94 °C. Anal. (C14H17NO4) C,H,N.
Fifty milliliters of 1 M LAH in THF was placed in an inert atmosphere, well stirred, and cooled to 0 °C with an external ice-bath. There was added, dropwise, 1.35 mL of 100% H2SO4 at a rate slow enough to minimize charring. There was then added, dropwise, 2.8 g 1-(2,5-dimethoxy-3,4-(trimethylene)phenyl)-2-nitropropene in 15 mL THF. At the end of the addition, the stirring was continued for an additional 0.5 h, and then the reaction mixture was held at reflux on the steam bath for another 0.5 h. After cooling again to ice-bath temperature, the excess hydride was destroyed with the addition of 11 mL IPA, followed by 5.5 mL 5% NaOH which converted the inorganic mass through a cottage cheese stage into a loose, filterable texture. The solids were removed by filtration, washed with additional THF, and the combined filtrates and washes stripped of solvent under vacuum. There was obtained 2.51 g of a white oil that was distilled at 115–135 °C at 0.2 mm/Hg to give 1.83 g of a clear colorless oil. This was dissolved in 8 mL IPA, neutralized with 28 drops of concentrated HCl, and diluted with 140 mL anhydrous Et2O. In about 0.5 h there started a slow snowfall of fine fluffy white crystals which was allowed to continue until no additional crystals appeared. After filtering, Et2O washing and air drying, there was obtained 1.81 g of 2,5-dimethoxy-3,4-(trimethylene)amphetamine hydrochloride (G-3) with a mp of 157–159 °C. Anal. (C14H22ClNO2) C,H.
DOSAGE: 12–18 mg.
DURATION: 8–12 h.
QUALITATIVE COMMENTS: (with 12 mg) “There was a warmth, a mellowness, as things developed. No body disturbance at all, but then there were no visuals either which, for me on this particular occasion, was disappointing. The day was consumed in reading, and I identified completely with the character of my fictional hero. It was a different form of fantasy. I think I prefer music as a structural basis for fantasy.”
(with 18 mg) “I am at a plus three, but I am not at all sure of why it is a plus three. With my eyes closed, there are puffy clouds, but no drama at all. Music was not exciting. There could well have been easy eroticism, but there was no push in that direction. No great amount of appetite. Not much of anything, and still a plus three. Simply lying still and surveying the body rather than the visual scene gave some suggestions of neurological sensitivity, but with getting up and moving about and doing things, all was fine. The next morning I was perhaps moving a bit more slowly than usual. I am not sure that there would be reward in going higher.”
EXTENSIONS AND COMMENTARY: In a comparison between the 2-carbon compound () and the 3-carbon compound (G-3) the vote goes towards the phenethylamine (the 2-carbon compound). With the first member of this series ( versus ) this was a stand-off, both as to quantitative effects (potency) and qualitative effects (nature of activity). Here, with the somewhat bulkier group located at the definitive 3,4-positions, the nod is to the shorter chain, for the first time ever. The potency differences are small, and maybe the amphetamine is still a bit more potent. But there are hints of discomfort with this latter compound that seem to be absent with the phenethylamine. The more highly substituted compounds (q.v.) more clearly define these differences.
26 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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