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#13 BOB
beta-METHOXY-2C-B; 4-BROMO-2,5-beta-TRIMETHOXYPHENETHYLAMINE
SYNTHESIS: To a vigorously stirred suspension of 2.1 g
4-bromo-2,5-dimethoxy-beta-nitrostyrene [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
tem
perature 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 BOD, BOH and BOM. 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 fol-lowed 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 2x50 mL
CH2Cl2, and the aqueous
phase
made basic with
NaOH. This was extracted with 2x50 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,beta-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!
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