β-Methoxy-2C-B · 4-Bromo-2,5-β-trimethoxyphenethylamine
#13 BOB SYNTHESIS: To a vigorously stirred suspension of 2.1 g [from 4-bromo-2,5-dimethoxybenzaldehyde and nitromethane in acetic acid with ammonium acetate as a catalyst, mp 157–158 °C, anal. (C10H10BrNO4) C,H] in 20 mL anhydrous MeOH, there was added a solution of sodium methoxide in MeOH (generated from 0.5 g metallic sodium in 20 mL anhydrous MeOH). After a few min there was added 10 mL acetic acid (no solids formed) followed by the slow addition of 50 mL of H2O. A cream-colored solid was produced, which was removed by filtration and washed well with H2O. After air drying the product, 1-(4-bromo-2,5-dimethoxyphenyl)-1-methoxy-2-nitroethane, weighed 2.0 g. An analytical sample from MeOH was off-white in color and had a mp of 119–120 °C. Anal. (C11H14BrNO5) C,H.
A solution of LAH (15 mL of 1 M solution in THF) was diluted with an equal volume of anhydrous THF, and cooled (under He) to 0 °C with an external ice bath. With good stirring there was added 0.38 mL 100% H2SO4 dropwise, to minimize charring. This was followed by the addition of 1.0 g 1-(4-bromo-2,5-dimethoxyphenyl)-1-methoxy-2-nitroethane as a solid over the course of 5 min. After an hour of stirring at 0 °C, the temperature was brought up to a gentle reflux on the steam bath for 30 min. There was no vigorous exothermic reaction seen, unlike that with the syntheses of , and . The reaction mixture was cooled again to 0 °C, and the excess hydride was destroyed by the cautious addition of IPA. This was followed by sufficent dilute aqueous NaOH to give a white granular character to the oxides, and to assure that the reaction mixture was basic. The reaction mixture was filtered, and the filter cake washed first with THF followed by IPA. The combined filtrate and washings were stripped of solvent under vacuum and dissolved in dilute H2SO4, with the apparent generation of yellow solids. This was washed with 2×50 mL CH2Cl2, and the aqueous phase made basic with NaOH. This was extracted with 2×50 mL CH2Cl2, and the pooled extracts were stripped of solvent under vacuum. The residue was distilled at 130–150 °C at 0.2 mm/Hg to give 0.2 g of product as a clear white oil. This fraction was dissolved in 10 mL IPA, and neutralized with 4 drops concentrated HCl. The addition of 30 mL anhydrous Et2O allowed the formation of 4-bromo-2,5,β-trimethoxyphenethylamine hydrochloride (BOB) as a fine white crystalline product. This was removed by filtration, washed with Et2O, and air dried. There was obtained 0.1 g white crystals with a mp of 187–188 °C. Anal. (C11H17BrClNO3) C,H.
DOSAGE: 10–20 mg.
DURATION: 10–20 h.
QUALITATIVE COMMENTS: (with 10 mg) “I don’t know if it was me this day, or if it was the chemical, but I got into a granddaddy of a paranoid, sociopathic snit, without feeling and without emotion. I was indifferent to everything. Later on, there was some improvement, with body tingling (good, I’m pretty sure) and a sense of awareness (good, I guess) but I still canceled my evening dinner company. All in all, pretty negative.”
(with 10 mg) “I had to get away and into myself, so I weeded in the vegetable garden for almost an hour. Then I lay down in the bedroom, and enjoyed a magnificent vegetable garden, in Southern France, in my mind’s eye. An extraordinary zucchini. And the weeds had all been magically pulled. In another couple of hours a neurological over-stimulation became apparent, and I spent the rest of the day defending myself. In the evening, I took 100 milligrams phenobarbital which seemed to smooth things just enough. Too bad. Nice material, otherwise.”
(with 15 mg) “The erotic was lustful, but at the critical moment of orgasm, the question of neurological stability became quite apparent. Does one really let go? Everything seemed a bit irritable. The tinnitus was quite bad, but the excitement of the rich altered place I was in was certainly worth it all. Through the rest of the day, I became aware of how tired I was, and how much I wanted to sleep, and yet how scared I was to give myself over to sleep. Could I trust the body to its own devices without me as an overseeing caretaker? Let’s risk it. I slept. The next day there was a memory of this turmoil. Clearly the first part of the experience might have been hard to define, but it was quite positive. But the last part makes it not really worth while.”
EXTENSIONS AND COMMENTARY: This compound, BOB, is the most potent of the BOX series. And yet, as with all of the members of this family, there are overtones of physical concern, and of some worry as to the integrity of the body. There may well be a separation of activity with the two optical isomers, but there is not a tremendous push to explore this particular family much further. They can’t all be winners, I guess. What would be the activities of compounds with a sulfur instead of an oxygen at the beta-oxygen position? What would be the nature of action if there were an alpha-methyl group, making all of these into amphetamine derivatives? Or what about both a sulfur and a methyl group? And what about the isomers that are intrinsic to all of this, the threo- and the erythro- and the “D’s” and the “L’s”? All this is terra incognita, and must someday be looked into. It is chemically simple, and pharmacologically provocative. Someone, somewhere, someday, answer these questions!
11 August 2018 · 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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