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#111 MDMEO
N-METHOXY-MDA; 3,4-METHYLENEDIOXY-N-METHYOXYAMPHETAMINE
SYNTHESIS: To a
solution of 20.9 g
methoxyamine hydrochloride in 75 mL
MeOH (a strongly acidic
solution) there was added 4.45 g
3,4-methylenedioxyphenylacetone (see under
MDMA for its preparation)
followed by 1.10 g
sodium cyanoborohydride. There was the immediate
formation of a solid
phase, and the evolution of what appeared to be
hydrogen
cyanide. To this there were added about 4 mL 5%
NaOH which
brought the
pH to the vicinity of 3 or 4. Another 1.0 g of
sodium
cyanoborohydride was added (no gas evolution this time) and stirring
was continued at ambient tem
perature for 6 days. All was added to 500
mL H2O, acidified with 10 mL HCl, and extraction with 3x100 mL
CH2Cl2
removed almost all the color. The aqueous
phase was made basic with
25%
NaOH, and extracted with 4x100 mL
CH2Cl2. Evaporation of the
solvent from these extracts yielded 1.8 g of a pale yellow oil which,
on
distillation at 90-95 °C at 0.5 mm/
Hg, gave a 1.6 g fraction of an
absolutely white, viscous, clear oil. This was
dissolved in 8 mL IPA
and neutralized with concentrated HCl. The product was an
exceptionally weak base, and appropriate end points must be respected
on the external
pH paper (yellow to red, rather than purple to
orange). Anhydrous
Et2O was added to the point of turbidity, and as
soon as
crystallization had actually started, more
Et2O was added with
stirring, for a net total of 200 mL. After a couple of h standing,
the fine white
crystalline 3,4-methylenedioxy-N-
methoxyamphetamine
hydrochloride (
MDMEO) was removed by filtration,
Et2O washed, and air
dried to constant weight. There was obtained 1.7 g of a product with
a mp of 143-146 °C. The proton
NMR was excellent with the N-
methoxyl
group a sharp singlet at 4.06 ppm. Anal. (
C11H16ClNO3) N.
DOSAGE: greater than 180 mgs.
DURATION: unknown
EXTENSIONS AND COMMENTARY: Why the interest in the N-methoxy
analogue
of
MDA? There are several reasons. One, this is an
isostere of
MDE
and it would be interesting to see if it might serve as a primer to
the promotion of the effectiveness of other drugs (see primer
discussion under MDPR). In one experiment, wherein a 60 microgram
dosage of LSD was used an hour and a half after a 180 milligram load
of
MDMEO, there was no augmentation of effects. Thus, it would appear
not to be a primer. Another reason for interest was that the
material, although having an extremely similar overall structure to
most of the active MD-series compounds, is very much a weaker base.
And
MDOH, which is also a very much weaker base than
MDA, still shows
the action and potency of
MDA. And, as this compound appears to be
inactive, base strength is not a sole predictor of activity.
The ultimate reason for making
MDMEO was, of course, that it could be
made. That reason is totally sufficient all by itself.
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