Phenescaline · 3,5-Dimethoxy-4-phenethyloxyphenethylamine
SYNTHESIS: To a solution of 5.8 g homosyringonitrile (see under 2CO3. The greenish mixture was refluxed for 3 days, with two additional 4 g batches of anhydrous K2CO3 being added at 24 h intervals. After addition to aqueous base, the product was extracted with CH2Cl2, the pooled extracts were washed with dilute base (the organic phase remained a deep purple color) and then finally with dilute HCl (the organic phase became a pale yellow). The solvent was removed giving 15.6 g crude 3,5-dimethoxy-4-phenethyloxyphenylacetonitrile which distilled at 165–185 °C at 0.3 mm/Hg to yield 3,5-dimethoxy-4-phenethyloxyphenylacetonitrile as a reddish viscous oil weighing 8.1 g. Anal. (C18H19NO3) C,H.
A solution of 7.9 g of distilled 3,5-dimethoxy-4-phenethyloxyphenylacetonitrile in 15 mL dry THF was added to a 0 °C solution of AH prepared from a vigorously stirred solution of 4.6 g LAH in 160 mL THF which had been treated, at 0 °C with 3.6 mL 100% H2SO4 under an atmosphere of He. The gelatinaceous reaction mixture was brought to a brief reflux on the steam bath, then cooled again. It was treated with 5 mL IPA which destroyed the unreacted hydride, followed by sufficient 15% NaOH to give loose, white filterable solids. These were removed by filtration and washed with THF. The filtrate and the washes were combined and, after removal of the solvent under vacuum, there remained 7.8 g of the product as a crude base which crystallized spontaneously. Distillation of this product at 170–180 °C at 0.35 mm/Hg gave 5.1 g white solids, with a mp of 85–86 °C from hexane. This base was dissolved in 20 mL warm IPA and treated with 1.6 mL concentrated HCl. To the resulting clear solution, there was added 75 mL anhydrous Et2O which gave, after a few moments of stirring, a spontaneous crystallization of 3,5-dimethoxy-4-phenethyloxyphenethylamine hydrochloride (PE) as beautiful white crystals. The weight was 5.4 g after air drying, and the mp was 151–152 °C. Anal. (C18H24ClNO3) C,H.
DOSAGE: greater than 150 mg.
QUALITATIVE COMMENTS: (with 150 mg) “At most, there was a bare threshold over the course of the afternoon. A vague unreal feeling, as if I had not had quite enough sleep last night. By late afternoon, even this had disappeared and I was left with an uncertainty that anything at all had occurred.”
EXTENSIONS AND COMMENTARY: There is not much there, so there is not much to make commentary on. This response is called a “threshhold” effect, and cannot be used to predict with any confidence just what level (if any) would produce psychological effects.
A similar chain on the 4-position, but with one less carbon atom, deserves special comment. Rather than a phenethyloxy group, this would be benzyloxy group (which in this day and age of Chemical Abstracts purity should probably be called a phenylmethoxy group). If one were to follow the naming philosophy of “
However, let’s be awkward and misleading, and call this benzyloxy-base
All of this says very little about PE. But then, there is very little to say about PE except that it may be active at very high levels, and I am not sure just how to get there safely.
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.
“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.”
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.
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,
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