From: [d--e] at [unislc.slc.unisys.com] (Dale Clark)
Subject: 2CB
Date: Mon, 14 Jun 1993 15:02:18 -0600 (MDT)
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2C-B
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GENERAL INFO
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4-bromo-2,5-dimethoxyphenethylamine. Phenethylamine analogue of DOB.
Bromomescaline. Melting point (hydrobromide salt) 214.5-215 C.
Melting point (acetate salt) 208-209 C.
STRUCTURE
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CH3O ----- ----- NH2
\ / \\ / \ /
|| |
/ \ // \
Br ----- OCH3
LD-50
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No citations are available regarding the LD-50 of 2C-B.
ACTIONS
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Doses are 12-24mg, Duration is 4-8 hours. Doses of 100mg have been taken
safely. 2C-B seems to be an extraordinarily colorful hallucingen similar
to LSD -- apparently somewhat analytical and dissasociative in higher doses
or in those sensitive to those effects.
At high doses (above 30 mgs.), 2C-B is intensely hallucinogenic,
and, like any major psychedelic, can be frightening for certain people.
In small doses, it becomes a mild sensory enhancer but does not have the
strongly empathogenic qualities that MDMA has.
Perhaps the best use that has been found for 2C-B is as a synergist
with MDMA. When taken together, the MDMA pushes the non-specific 2C-B
reaction in a more warm and emphathetic direction. Because 2C-B is a
psychedelic drug, and therefore not fully predictable, its action can take
the user in many different directions. But if the set and setting are right,
2C-B can enhance the desire for sexual orgasm during an MDMA experience.
The synergy of the two substances can on occasion be a true aphrodisiac.
DRUG INTERACTIONS
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Chlorpromazine may aggravate unpleasant psychological
symptoms.
CREATION PROCESS
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A solution of 100 g of 2,5-dimethoxybenzaldehyde in 220 g
nitromethane was treated with 10 g anhydrous ammonium acetate, and
heated on a steam bath for 2.5 h with occasional swirling. The
deep-red reaction mixture was stripped of the excess nitromethane
under vacuum, and the residue crystallized spontaneously. This crude
nitrostyrene was purified by grinding under IPA, filtering, and
air-drying, to yield 85 g of 2,5-dimethoxy-beta-nitrostyrene as a
yellow-orange product of adequate purity for the next step. Further
purification can be achieved by recrystallization from boiling IPA.
In a round-bottomed 2 L flask equipped with a magnetic stirrer and
placed under an inert atmosphere, there was added 750 mL anhydrous
THF, containing 30 g LAH. There was then added, in THF solution, 60 g
2,5-dimethoxy-beta-nitrostyrene. The final solution was a dirty
yellow-brown color, and it was kept at reflux temperature for 24 h.
After cooling, the excess hydride was destroyed by the dropwise
addition of IPA. Then 30 mL 15% NaOH was added to convert the
inorganic solids to a filterable mass. The reaction mixture was
filtered and the filter cake washed first with THF and then with MeOH.
The combined mother liquors and washings were freed of solvent under
vacuum and the residue suspended in 1.5 L H2O. This was acidified
with HCl, washed with with 3x100 mL CH2Cl2, made strongly basic with
25% NaOH, and reextracted with 4x100 mL CH2Cl2. The pooled extracts
were stripped of solvent under vacuum, yielding 26 g of oily residue,
which was distilled at 120-130 deg C at 0.5 mm/Hg to give 21 g of a white
oil, 2,5-dimethoxy-phenethylamine (2C-H) which picks up carbon dioxide
from the air very quickly.
To a well-stirred solution of 24.8 g 2,5-dimethoxyphenethylamine in 40
mL glacial acetic acid, there was added 22 g elemental bromine
dissolved in 40 mL acetic acid. After a couple of min, there was the
formation of solids and the simultaneous evolution of considerable
heat. The reaction mixture was allowed to return to room temperature,
filtered, and the solids washed sparingly with cold acetic acid. This
was the hydrobromide salt. There are many complicated salt forms,
both polymorphs and hydrates, that can make the isolation and
characterization of 2C-B treacherous. The happiest route is to form
the insoluble hydrochloride salt by way of the free base. The entire
mass of acetic acid-wet salt was dissolved in warm H2O, made basic to
at least pH 11 with 25% NaOH, and extracted with 3x100 mL CH2Cl2.
Removal of the solvent gave 33.7 g of residue which was distilled at
115-130 !C at 0.4 mm/Hg. The white oil, 27.6 g, was dissolved in 50
mL H2O containing 7.0 g acetic acid. This clear solution was vigorous
stirred, and treated with 20 mL concentrated HCl. There was an
immediate formation of the anhydrous salt of
2,5-dimethoxy-4-bromophenethylamine hydrochloride (2C-B). This mass
of crystals was removed by filtration (it can be loosened considerably
by the addition of another 60 mL H2O), washed with a little H2O, and
then with several 50 mL portions of Et2O. When completely air-dry,
there was obtained 31.05 g of fine white needles, with a mp of 237-239
deg C with decomposition. When there is too much H2O present at the time
of adding the final concentrated HCl, a hydrated form of 2C-B is
obtained.