3,5-Dimethoxy-4-(2-propynyloxy)phenethylamine
#143 PROPYNYL SYNTHESIS: To a solution of 5.8 g homosyringonitrile (see under for its preparation) in 50 mL acetone containing 100 mg decyltriethylammonium iodide, there was added 12 g of an 80% solution of propargyl bromide in toluene and 6.9 g of finely powdered anhydrous K2CO3. This mixture was held at reflux on the steam bath for 12 h, after which the solvent was removed under vacuum. The residues were added to 0.5 L H2O, acidified, and extracted with 3×75 mL CH2Cl2. The extracts were pooled, washed with 5% NaOH, and then with dilute HCl which discharged the deep color. Removal of the organic solvent under vacuum yielded 6.6 g of crude product. This was distilled at 138–148 °C at 0.25 mm/Hg, yielding 4.3 g 3,5-dimethoxy-4-(2-propynyloxy)phenylacetonitrile which spontaneously crystallized. A small sample from MeOH had a mp of 94–95 °C. Anal. (C13H13NO3) C,H.
A suspension of 2.8 g LAH in 70 mL anhydrous THF was cooled to 0 °C with good stirring under He, and treated with 2.0 g 100% H2SO4. To this, a solution of 4.2 g 3,5-dimethoxy-4-(2-propynyloxy)phenylacetonitrile in 30 mL anhydrous THF was added very slowly. After the addition had been completed, the reaction mixture was held at reflux on the steam bath for 0.5 h, cooled to room temperature, treated with IPA to decompose the excess hydride, and finally with 15% NaOH to convert the solids to a white filterable mass. The solids were separated by filtration, the filter cake was washed with THF, and the filtrate and washes were pooled. After removal of the solvent, the residue was added to 100 mL dilute H2SO4, and washed with 3×75 mL CH2Cl2. The aqueous phase was made basic with dilute NaOH, and the product extracted with 2×75 mL CH2Cl2. After removal of the solvent under vacuum, the residue was distilled at 125–155 °C at 0.3 mm/Hg to provide 2.4 g of a light amber viscous liquid. This was dissolved in 10 mL IPA, acidified with concentrated HCl until a droplet produced a red color on dampened, external universal pH paper, and then diluted with 40 mL anhydrous Et2O with good stirring. After a short delay, 3,5-dimethoxy-4-(2-propynyloxy)phenethylamine hydrochloride (PROPYNYL) spontaneously crystallized. The product was removed by filtration, washed first with an IPA/Et2O mixture, and finally with Et2O. The yield was 3.0 g of white needles.
DOSAGE: 80 mg or more.
DURATION: 8–12 h.
QUALITATIVE COMMENTS: (with 55 mg) “I have cold feet—literally—I don’t mean that in the spiritual or adventurous sense. But also I am somewhat physically fuzzy. I feel that if I were in public my behavior would be such that someone would notice me. Everything was OK without any question at the ninth hour. I could walk abroad again.”
(with 80 mg) “There is a body load. The flow of people around me all day has demanded my attention, and when I had purposefully retreated to be by myself, there was no particular reward as to visuals or anything with eyes closed, either. Sleep was easy at midnight (the twelth hour of the experiment) but the morning was sluggish, and on recalling the day, I am not sure of the events that had taken place. Higher might be all right, but watch the status of the body. There certainly wasn’t that much mental stuff.”
EXTENSIONS AND COMMENTARY: No experiments have been performed that describe the action of this drug at full level. This compound does not seem to have the magic that would encourage exploration at higher levels.
13 May 2016 · 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 history 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.
Transform Press,
Box 13675
Berkeley, CA 94701

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