SYNTHESIS: To a well stirred solution of 1.64 g of
1-(N-(benzyloxycarbonyl)amino)-1,1-dimethyl-2-(3,4-methylenedioxyphenyl)ethane
(see under MDPH for its preparation) in 10 mL anhydrous THF there was
added a suspension of 0.38 g LAH in 25 mL THF. All was held at reflux
for 24 h, the excess hydride was destroyed by the addition of 1.5 mL
H2O, and sufficient aqueous NaOH was added to make the reaction
mixture basic and flocculant enough to be filterable. The inorganic
solids were removed by filtration and, following washing with THF, the
combined filtrate and washings were stripped of organic solvent under
vacuum. The residue was dissolved in 100 mL Et2O and washed with 2x50
mL saturated aqueous NaHCO3. After drying the organic phase with
anhydrous MgSO4, the solvent was removed under vacuum to give a yellow
oil. This was dissolved in 50 mL absolute EtOH and neutralized with
concentrated HCl. Removal of the solvent under vacuum yielded an
off-white solid that was recrystallized from an EtOH/EtOAc mixture to
provide 0.84 g of a,a,N-trimethyl-3,4-methylenedioxyphenethylamine
hydrochloride (MDMP) with a mp of 206-208 °C. The NMR spectrum showed
the a,a-dimethyl pair as a singlet at 1.38 ppm. Anal. (C12H18ClNO2)
C,H,N.
DOSAGE: above 110 mg.
DURATION: perhaps 6 hours.
QUALITATIVE COMMENTS: (with 60 mg) There was a faint, dull alerting
at just over a half hour. The time sense was out of order, and an
absence of visuals but a generalized attentiveness to my surroundings
was suggestive of MDMA. Nothing remained at the six hour point.
(with 110 mg) There was a light-headedness, and a complete absence of
libido. Nothing in any way psychedelic, but there are hints of
discomfort (jaw tension) that will bear close watching at higher
dosages. It might evolve at higher levels into something like MDMA.
EXTENSIONS AND COMMENTARY: This is one of several candidates for
clinical use as a substitute for MDMA, but there will have to be a
much broader study of its qualitative action in man. It is clearly
not psychedelic at these modest levels, and in in vitro animal studies
it was apparently inactive as a serotonin releaser. The warped logic
for looking at phentermine analogs was discussed in the comments that
concerned MDPH. The initials used here have been chosen with care.
MDM should not be used as it has found some currency as an
abbreviation for MDMA (Methylene-Dioxy-Methamphetamine). MDMP fits
neatly with Methylene-Dioxy-Me-Phentermine.
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