This is a recipe from
PiHKAL. If you're interested in how the hardlinks
were chosen, read
noding PiHKAL for Everything2.
#95 LOPHOPHINE
3-METHOXY-4,5-METHYLENEDIOXYPHENETHYLAMINE
SYNTHESIS: A
solution of 50 g
myristicinaldehyde
(
3-methoxy-4,5-methylenedioxybenzaldehyde, see under M
MDA for its
preparation) in 200 mL acetic acid was treated with 33 mL
nitromethane
and 17.4 g
anhydrous ammonium acetate and held on the steam bath for 5
h. The reaction mixture was diluted with a little H2O and cooled in
an external ice-
acetone bath. A heavy crop of yellow
crystals formed,
which were removed by filtration, washed with cold acetic acid, and
dried to constant weight. There was thus obtained 19.3 g
3-methoxy-4,5-methylenedioxy-beta-nitrostyrene with a mp of 210-212 °C.
The mother liquors were diluted with H2O, and extracted with 3x100 mL
CH2Cl2. The pooled extracts were washed with 5%
NaOH, and the
solvent
removed under vacuum yielding 34 g of a dark residue that was largely
unreacted
aldehyde. This residue was reprocessed in acetic acid with
nitromethane and
ammonium acetate, as described above, and provided an
additional 8.1 g of the
nitrostyrene with the same mp.
A suspension of 25 g LAH in 1.5 L
anhydrous Et2O in an inert
atmosphere was stirred
magnetically, and brought up to a gentle
reflux. Through a Soxhlet
condenser modified to allow
Et2O to return
continuously to the reaction mixture, there was added 27.0 g of
3-methoxy-4,5-methylenedioxy-beta-nitrostyrene. The addition require
many h, and when it was completed, the reaction was held at reflux for
an additional 9 days. After cooling the reaction mixture in an
external ice bath, the excess
hydride was destroyed by the cautious
addition of dilute H2SO4. The final amount used was 1800 mL H2O
containing 133 g H2SO4. The
phases were separated, and the aqueous
phase was washed with 2x100 mL
Et2O. To it was then added 625 g
potassium sodium tartrate, and sufficient base to bring the
pH to >9.
This was extracted with 3x250 mL
CH2Cl2, and the pooled extracts
stripped of
solvent under vacuum. The residue was
dissolved in
anhydrous Et2O and saturated with anhydrous HCl gas, giving a heavy
crystallization of salts. These were removed by filtration,
Et2O
washed, and air dried, to give 17.7 g
3-methoxy-4,5-methylenedioxyphenethylamine (LOPHOPHINE) as an
off-white solid with a mp of 160-161 °C. This was
dissolved in
CH3CN
containing 5%
EtOH, decolorized with activated charcoal, filtered, and
the removed charcoal washed with boiling
CH3CN. Slow cooling of the
solution provided 11.7 g of a white product which melted at 164-164.5
°C.
DOSAGE: greater than 200 mg.
DURATION: unknown.
QUALITATIVE COMMENTS: (with 150 mg) Between two and five hours, very
peaceful and
euphoric mood elevation, similar to mescaline, but
without any visual distortion. Mild enhancement of color perception,
possibly a function of mood elevation. There was no nausea, no
eyes-closed vision. Slept easily that evening.
(with 250 mg) Possibly something of a threshold effect from 2:30 to
4:30 of the experiment. Intangible, and certainly there is nothing an
hour later.
EXTENSIONS AND COMMENTARY: It looks as if this compound is not active.
There is an excellent argument as to why it really should be, and the
fact that it is not active is completely unexpected. Let me try to
explain.
Quite simply, mescaline is a major component and a centrally active
alkaloid of the Peyote plant. It is a
phenethylamine, which can
undergo a
cyclization within the plant to produce a pile of
derivatives (
tetrahydroisoquinolines) such as
anhalonine and
O-
methylanhalonidine that are marvelously complex
alkaloids, all
natural components of this magical cactus. But there is another pile
of derivatives (
tetrahydroisoquinolines) such as
anhalonine, and
lophophorine, and
peyophorine which are the logical
cyclization
products of another
phenethylamine which does not exist in the cactus.
It should be there, but it is not. If it were there it would be the
natural precursor to a host of bi
cyclic alkaloids, but it is absent.
This is
3-methoxy-4,5-methylenedioxyphenethylamine. I feel that some
day it will be discovered as a plant component, and when it is it can
be given a name that reflects the generic
binomial of the plant. And
since the plant has been known as Lophophora williamsii, why not give
a name to this compound (which should be in the plant), one derived
from the Latin name, but one that has never before been used? What
about LOPHOPHINE? And so, I have named it, but I have not found it,
nor has anyone else. Yet.
It is inevitable that this simple and most appealing precursor will be
found to be present in the cactus, at some future time when we will
have tools of sufficient sensitivity to detect it. And certainly, it
would be reasonable to expect it to be an active
psychedelic, and to
be as interesting in man as its close cousin, mescaline. But, at the
present time, LOPHOPHINE is not known to be present in the plant, and
it is not known to be active in man. I am confident that both
statuses will change in the future.
Back to PiHKAL?