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#141 PE
PHENESCALINE; 3,5-DIMETHOXY-4-PHENETHYLOXYPHENETHYLAMINE
SYNTHESIS: To a
solution of 5.8 g
homosyringonitrile (see under E for
its preparation) in 50 mL of
acetone containing 100 mg
decyltriethylammonium iodide, there was added 14.8 g
beta-phenethylbromide and 6.9 g of finely powdered
anhydrous K2CO3. The
greenish mixture was refluxed for 3 days, with two additional 4 g
batches of
anhydrous K2CO3 being added at 24 h intervals. After
addition to aqueous base, the product was extracted with
CH2Cl2, the
pooled extracts were washed with dilute base (the organic
phase
remained a deep purple color) and then finally with dilute HCl (the
organic
phase became a pale yellow). The
solvent was removed giving
15.6 g crude
3,5-dimethoxy-4-phenethyloxyphenylacetonitrile which
distilled at 165-185 °C at 0.3 mm/
Hg to yield
3,5-dimethoxy-4-phenethyloxyphenylacetonitrile as a reddish viscous
oil weighing 8.1 g. Anal. (
C18H19NO3) C,H.
A
solution of 7.9 g of
distilled
3,5-dimethoxy-4-phenethyloxyphenylacetonitrile in 15 mL dry THF was
added to a 0 °C
solution of AH prepared from a vigorously stirred
solution of 4.6 g LAH in 160 ml THF which had been treated, at 0 °C
with 3.6 mL 100% H2SO4 under an
atmosphere of He. The gelatinaceous
reaction mixture was brought to a brief reflux on the steam bath, then
cooled again. It was treated with 5 mL IPA which destroyed the
unreacted
hydride, followed by sufficient 15%
NaOH to give loose,
white filterable solids. These were removed by filtration and washed
with THF. The filtrate and the washes were combined and, after
removal of the
solvent under vacuum, there remained 7.8 g of the
product as a crude base which
crystallized spontaneously.
Distillation of this product at 170-180 °C at 0.35 mm/
Hg gave 5.1 g
white solids, with a mp of 85-86 °C from hexane. This base was
dissolved in 20 mL warm IPA and treated with 1.6 mL concentrated HCl.
To the resulting clear
solution, there was added 75 mL
anhydrous Et2O
which gave, after a few moments of stirring, a spontaneous
crystallization of
3,5-di-methoxy-4-phenethyloxyphenethylamine
hydrochloride (PE) as beautiful white
crystals. The weight was 5.4 g
after air drying, and the mp was 151-152 °C. Anal. (
C18H24ClNO3) C,H.
DOSAGE: greater than 150 mg.
DURATION: unknown.
QUALITATIVE COMMENTS: (with 150 mg) At most, there was a bare
threshold over the course of the afternoon. A vague unreal feeling,
as if I had not had quite enough sleep last night. By late afternoon,
even this had disappeared and I was left with an uncertainty that
anything at all had occurred.
EXTENSIONS AND COMMENTARY: There is not much there, so there is not
much to make commentary on. This response is called a "threshhold"
effect, and cannot be used to predict with any confidence just what
level (if any) would produce
psychological effects.
A similar chain on the 4-position, but with one less
carbon atom,
deserves special comment. Rather than a
phenethyloxy group, this
would be
benzyloxy group (which in this day and age of
Chemical
Abstracts purity should probably be called a
phenylmethoxy group). If
one were to follow the naming
philosophy of R
proscaline equals P and
buscaline equals BS convention, one would call it 4-
benzescaline, and
give it the code name BZ. The
nomenclature purist would probably call
the compound PM (for
phenylmescaline or, more likely
phenylmethoxydimethoxyphenethylamine), since the term BZ is awkward
and misleading. It is a code name that has been given to a potent CNS
agent known as
quinuclidin-3-yl
benzilate, which is a chemical and
biological warfare (CBW) incapacitating agent currently being stored
by the military to the extent of 20,000 pounds. And, BZ has also
recently become the jargon name given to
benzodiazepine receptors.
They have been called the BZ-receptors.
However, let's be awkward and misleading, and call this
benzyloxy-base
BZ. For one thing, the three-
carbon analogue 3C-BZ has already been
described in its own recipe using this code. And the 4-
fluoroanalogue
of it, 3C-FBZ, is also mentioned there. And BZ has already been
described
synthetically, having been made in exactly the procedure
given for escaline, except that the reduction of the
nitrile was not
done by
catalytic hydrogenation but rather by
sodium borohydride in
the presence of
cobalt chloride. It has been shown to be a effective
serotonin agonist, and may warrant human experimentation. The
serotonin activity suggests that it might be active at the same levels
found for
proscaline.
All of this says very little about PE. But then, there is very little
to say about PE except that it may be active at very high levels, and
I am not sure just how to get there safely.
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