3,4-Dimethoxy-β-hydroxyphenethylamine
#57 DME SYNTHESIS: To a solution of 10.2 g 3,4-dimethoxybenzaldehyde in 10 mL EtOH, cooled to 0 °C, there was added a solution of 4.2 g KCN in 40 mL H2O. With good stirring, there was slowly added 10 mL concentrated HCl (caution: HCN is evolved) and the two-phase reaction mixture was allowed to continue stirring until there was the spontaneous formation of crystals. After a few days standing, these were removed by filtration and well washed with H2O. All was recrystallized from 75 mL of 50% MeOH and air dried to provide 6.95 g of the cyanohydrin 3,4-dimethoxy-α-hydroxyphenylacetonitrile. The mp was 104–106 °C, which can be increased to 109 °C by recrystallization from benzene.
A well-stirred suspension of 4.7 g LAH in 500 mL anhydrous Et2O was brought up to a gentle reflux, and 4.7 g 3,4-dimethoxy-α-hydroxyphenylacetonitrile was leached in from a Soxhlet thimble, over the course of 3 h. The color of the ether solution progressed from yellow to green, to an eventual blue. The reflux was maintained for 16 h. After cooling again, there was added (carefully) a solution of 27 g H2SO4 in 500 mL H2O. The completely clear two-phase mixture was separated, and the aqueous phase treated with 87 g potassium sodium tartrate. The addition of 25% NaOH brought the pH >9, and this phase was extracted with 4×100 mL CH2Cl2. Removal of all the organic solvents under vacuum gave a residue that was part oil and part solid. This was extracted with 4×50 mL boiling Et2O, the extracts pooled, and saturated with anhydrous HCl gas. The 0.95 g of pale-yellow crystals that formed were removed by filtration, and finely ground under 5 mL CH3CN. There remained, after refiltration and air drying, 0.85 g of 3,4-dimethoxy-β-hydroxyphenethylamine hydrochloride, DME, with a mp of 170–172 °C.
DOSAGE: greater than 115 mg.
DURATION: unknown.
QUALITATIVE COMMENTS: (with 115 mg) “I was faintly nauseous about an hour after taking the compound, and perhaps I was more alert than usual in the evening. Substantially no effects.”
EXTENSIONS AND COMMENTARY: The rationale for exploring the beta-hydroxylated phenethylamines, especially those with oxygens at the biologically important 3- and 4-positions, has already been presented. is a beta-hydroxylated phenethylamine with oxygens at these two ring positions. With DME, these are masked as two methyl ethers, and the initials DME stand for 3,4-dimethoxyphenyl-β-ethanolamine. This is an alternate name for 3,4-dimethoxy-β-hydroxyphenethylamine.
An exactly analogous compound is 3,4-methylenedioxy-β-ethanolamine, where the masking is done with the biologically more fragile methylenedioxy ether. Originally I had called this compound MDE (methylenedioxyethanolamine) but that code has been, since 1975, used exclusively for , which is a recipe all by itself. Under the discussion of members of the BOX series, there is a methylenedioxyphenethylamine with a methoxyl group at the beta-position, and it is called (q.v.). There, a reasonable code name for this specific compound is given, namely . “BO” stands for the beta-oxygen function on a phenethylamine; this is the heart of the BOX family. The “H” which is the third letter of BOHH stands for the free hydroxyl group. And the final “H” is for (which is the trivial name for the compound without the hydroxyl group). BOHH, or 3,4-methylenedioxy-β-hydroxyphenethylamine, or 3,4-methylenedioxy-β-ethanolamine, has also be assayed in man at up to 100 milligrams without any effects, and must be considered, as of now, to be inactive centrally. The possible toxic roles of beta-ethanolamines as potential adrenolytic agents, have been discussed in the recipe. And beware of the use of the code name MDE in the very old literature. It might be this BOHH compound.
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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