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Book II of PiHKAL: A Chemical Love Story, by Alexander & Ann Shulgin #15: BOH
#15 BOH: β-Methoxy-3,4-methylenedioxyphenethylamine

#15 BOH SYNTHESIS: To a solution of 30 g piperonal in 100 mL acetic acid there was added 20 mL nitromethane and 10 mL cyclohexylamine. After heating on the steam bath for 1.5 h, the reaction mixture started to crystallize. The mixture was cooled in an ice bath, and the heavy mass of deposited crystals removed by filtration and washed with 20 mL acetic acid. All was supended in 100 mL warm MeOH, cooled again, and filtered to give 24.5 g of 3,4-methylenedioxy-β-nitrostyrene as canary-yellow crystals, with a mp of 158–160 °C. Reduction of this compound with LAH gives rise to MDPEA, which is a separate entry with a recipe of its own.

To a vigorously stirred suspension of 20 g 3,4-methylenedioxy-β-nitro -styrene in 100 mL anhydrous MeOH there was added a freshly prepared solution of 5.5 g elemental sodium in 100 mL MeOH. The nitrostyrene goes into solution over the course of 5 min. There was then added, first, 50 mL acetic acid with the stirring continued for an additional 1 min. There was then added 300 mL H2O. An oil separated and was extracted into 200 mL CH2Cl2. The organic extract was washed with 500 mL dilute aqueous NaHCO3, followed by 500 mL H2O. Removal of the solvent gave a residue that was distilled at 128–145 °C at 0.4 mm/Hg, providing 16.6 g of a yellow viscous liquid which slowly crystallized. An analytical sample was recrystallized from four volumes of MeOH to give 1-methoxy-1-(3,4-methylenedioxyphenyl)-2-nitroethane as bright yellow crystals with a mp of 58–59 °C. Anal. (C10H11NO5) C,H.

A solution of LAH (100 mL of 1 M solution in THF) was cooled, under He, to 0 °C with an external ice bath. With good stirring there was added 2.5 mL 100% H2SO4 dropwise, to minimize charring. This was followed by the addition of 12 g 1-methoxy-1-(3,4-methylenedioxyphenyl)-2-nitroethane over the course of 2 min. There was an immediate loss of color. After a few minutes further stirring, the temperature was brought up to a reflux with a heating mantle. There was a gentle gas evolution for a few min, followed by an exothermic reaction that exceeded the capacity of the condenser. Once the reaction had subsided, the unreacted hydride was destroyed with a minimum of IPA, and 15% NaOH was added to convert the inorganics to a loose white filterable mass. The reaction mixture was filtered, and the filter cake washed thoroughly with THF. The combined filtrate and washes were stripped of solvent under vacuum, providing an orange oil. This was dissolved in 400 mL dilute H2SO4, which was washed with 3×75 mL CH2Cl2. After making the aqueous phase basic, it was extracted with 2×100 mL CH2Cl2. The pooled extracts were stripped of solvent under vacuum, and the residue distilled at 103–112 °C at 0.5 mm/Hg. There was obtained 2.5 g of a colorless, viscous oil which was dissolved in 25 mL IPA, neutralized with 45 drops of concentrated HCl, and finally diluted with 30 mL anhydrous Et2O. There was thus formed beta-methoxy-3,4-methylenedioxyphenethylamine hydrochloride (BOH) as a fine white crystalline product. The mp was 105–106.5 °C, with bubbling and darkening. The mp properties proved to be inconsistent, as the salt was a hydrate. Recrystallization from CH3CN, or simply heating to 100 °C in toluene, converted the salt to an anhydrous form, with mp of 152–153 °C. Anal. (C10H14ClNO3) C,H.

DOSAGE: 80–120 mg.

DURATION: 6–8 h.

QUALITATIVE COMMENTS: (with 90 mg) “Distinct body awareness in an hour. The threshold is mostly physical. Faint sense of inside warmth, skin prickling, cold feet, loose bowels, anorexia. By the fifth hour, I was on the downslope, and in retrospect I found it good humored but not insightful.”

(with 100 mg) “There was a vague nausea, and a chilling of the feet. It reached a real plus two, with dilated pupils and quite a thirst. How can one describe the state? There were no visuals, and I was not even stoned. I was just very turned on. And I was completely back to baseline by hour number six.”

EXTENSIONS AND COMMENTARY: There are several reports of a nice, mild mood enhancement in the 20–40 milligram dosage area, but searches for psychedelic effects at higher levels gave a strange mix of some sort of an altered state along with bodily discomfort. The BOH name for this member of the BOX family follows the convention discussed in the BOD recipe—with “H” for homopiperonylamine, the simplest of the muni-metro family, q.v. The demethylated homologue of BOH is BOHH, and is the methylenedioxy analogue of norepinephrine. It might well hydrolytically open up in the body to provide this neurotransmitter, and serve as some sort of transmitter in its own right. It is discussed under DME.

Maybe there is something to the concept that when you imitate a neurotransmitter too closely, you get a hybrid gemisch of activity. The term “pro-drug” is used to identify a compound that may not be intrinsically active, but one which metabolizes in the body to provide an active drug. I feel the term should have been pre-drug, but pro-drug was the word that caught on. BOH may well act in the body as a pro-drug to norepinephrine, but with the temporary blocking of the polar functions with ether groups, it can gain access to the brain. And once there, it can be stripped of these shields and play a direct neurological role. I uncovered a very similar analogy in the tryptamine world some years ago. Just as norepinephrine is a neurotransmitter, so is serotonin. And I found that by putting an O-ether on the indolic phenol (to hide its polarity) and an alpha-methyl group next to the primary amine (to protect it from metabolic deaminase), it became an extremely potent, and most complex, psychedelic. This was the compound α,O-dimethylserotonin, or α,O-DMS. There is an uncanny analogy between this tryptamine and the phenethylamine BOH.

Somehow the quiet voice deep inside me says, don’t use too much, too quickly. Maybe one of the optical isomers is the body thing, and the other isomer is the mind thing. So far, only the racemic mixture has been tasted, to the best of my knowledge.

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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. Still others remain to be added.

I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore most of the typographic niceties found in the printed edition. I’ve also made minor changes to some chemical names in line with current nomenclature practice, and in the hope of aligning with more readers’ searches. Typically the change is little more than expanding a prefix and setting it in italics. The errata and changes 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.

Although 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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