#124 META-DOB SYNTHESIS: The reaction of 2,4-dimethoxyamphetamine () with elemental bromine proceeded directly to the formation of 5-bromo-2,4-dimethoxyamphetamine which was isolated as the hydrobromide salt with a melting point of 204.5–205.5 °C and in a 67% yield. A mp of 180–181 °C has also been published.
DOSAGE: 50–100 mg.
DURATION: 5–6 h.
EXTENSIONS AND COMMENTARY: There is very little synthetic information available, and some of it is contradictory. The initial human report in the medical literature says only that a dosage of about 100 milligrams produced effects that were similar to those produced by . Both the quality of the experience and the potency of the compound have been modified in more recent publications by the originators of this compound. A 40 milligram dose, after an induction period of an hour, produced a vague uneasiness that was interpreted originally as a threshold psychedelic effect. At doses in the 60 to 90 milligram range, there were produced feelings of anxiety and paranoid fantasies, and distinct toxic signs such as flushing, palpitations, and occasional nausea, vomiting and diarrhea. Any psychedelic effects seem to have been blurred by the more obvious toxic actions of the drug. I have been told that their final conclusion was that the drug appears toxic in the 50 to 60 milligram range. I have not personally explored this positional isomer of .
The positional isomer of with the bromine in the ortho-position is 4,5-dimethoxy-2-bromoamphetamine and is called, not surprisingly, . It has been made by the condensation of 2-bromo-4,5-dimethoxybenzaldehyde with nitroethane to give 1-(2-bromo-4,5-dimethoxyphenyl)-2-nitropropene with a mp of 105–106 °C. Reduction to the amphetamine had to be conducted at a low temperature and using only an equimolar amount of lithium aluminum hydride, to minimize reductive removal of the bromo group. The hydrochloride salt of 2-bromo-4,5-dimethoxyamphetamine (ORTHO-DOB) had a mp of 214–215.5 °C, and the hydrobromide salt a melting point of 196–197 °C or of 210 °C. Both have been reported. The yield from the direct bromination of was apparently very bad. I do not think that the compound has ever gone into man.
There are three other dimethoxyamphetamine isomers known, and each has been explored chemically as to its reactivity with elemental bromine. With , a mixture of the and was formed; with , was formed; and with , a mixture of and the 2,6-dibromo product () was produced. The bromination of is, of course, the preferred procedure for the synthesis of 4-Br-2,5-DMA, or , q.v. None of these positional isomers has evear ever been put into man, but 3-Br-2,6-DMA and the iodo-counterpart () have been explored as potential radio-fluorine carriers into the brain. This is all discussed in the recipe.
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

510 · 934 · 4930 (voice)
510 · 934 · 5999 (fax)