SYNTHESIS: To a vigorously stirred suspension of 9.0 g
beta-nitro-3,4,5-trimethoxystyrene (see under the recipe for M for the
preparation of this intermediate) in 50 mL anhydrous MeOH there was
added a solution obtained from the addition of 2.0 g metallic sodium
to 50 mL anhydrous MeOH. The bright orange color faded to a light
cream as the nitrostyrene went into solution. After 3 min there was
added 30 mL acetic acid, which produced white solids, and this was
followed by further dilution with 150 mL H2O. The formed solids were
removed by filtration, washed well with H2O, and recrystallized from
150 mL boiling MeOH. After removal of the product by filtration and
air drying to constant weight, there was obtained 6.9 g of
1-methoxy-2-nitro-1-(3,4,5-trimethoxyphenyl)ethane as fine,
cream-colored crystals. The mp was 143-144 °C, and the Rf by TLC
(silica-gel plates and CH2Cl2 as moving phase) was identical to that
of the starting aldehyde. Anal. (C12H17NO6) C,H.
A solution of LAH (50 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
1.25 mL 100% H2SO4 dropwise, to minimize charring. This was followed
by the addition of 6 g of solid
1-methoxy-2-nitro-1-(3,4,5-trimethoxyphenyl)ethane over the course of
2 min. There was some gas evolution. After 5 min additional
stirring, the temperature was brought up to a reflux with a heating
mantle. There was a gentle gas evolution for a few minutes, followed
by an exothermic reaction with vigorous gas evolution. Once
everything had settled down, the reaction mixture was held at reflux
temperature for an additional 2 h. The excess hydride was destroyed
by the addition of IPA and 15% NaOH was added to convert the inorganic
salts 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
which provided a red-brown liquid. This was dissolved in dilute H2SO4
and washed with 3x75 mL CH2Cl2. After making the aqueous phase basic
with NaOH, it was extracted with 2x100 mL CH2Cl2. The pooled extracts
were stripped of solvent under vacuum, and the colorless residue
distilled at 120-150 °C at 0.3 mm/Hg. There was obtained 2.8 g of a
colorless oil which was dissolved in 30 mL IPA and neutralized with
concentrated HCl, allowing the spontaneous formation of the
hydrochloride salt. This was diluted with 75 mL anhydrous Et2O,
yielding 2.8 g 3,4,5,beta-tetramethoxyphenethylamine hydrochloride (BOM)
as a white crystalline product. This had a mp of 198.5-199.5 °C.
Anal. (C12H20ClNO4) C,H.
DOSAGE: greater than 200 mg.
DURATION: unknown.
EXTENSIONS AND COMMENTARY: There are some indicators of central
activity with assays involving both the 120 milligram and the 180
milligram levels, but nothing that can be rated as over a plus one.
It can be seen with the two active members of the BOX series (BOD and
BOB) that the potency is about equal to, or a little more (up to a
factor of maybe x2), than the analogue without the methoxyl group on
the aliphatic chain. If this formula were to hold in the relationship
between mescaline and BOM, the active level might well be in the
200-400 milligram range. But at the moment, it remains unknown.
Again, the name of the compound (BOM) is from the RBO-S prefix of this
family (from benzyl + oxy), plus the RMS of mescaline (which has
provided the ring substitution pattern).
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