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#126 METHYL-DMA
DMMA; 2,5-DIMETHOXY-N-METHYLAMPHETAMINE
SYNTHESIS: To a stirred
solution of 28.6 g
methylamine hydrochloride
in 120 mL MeOH there was added 7.8 g
2,5-dimethoxyphenylacetone
followed by 2.6 g
sodium cyanoborohydride. HCL was added as needed to
maintain the
pH at about 6. The reaction was complete in 24 h, but
was allowed to stir for another 3 days. The reaction mixture was
poured into 600 mL H2O, acidified with HCl (HCN evolution, caution)
and washed with 3x100 mL
CH2Cl2. Aqueous
NaOH was added, making the
solution strongly
alkaline, and this was then extracted with 3x100 mL
CH2Cl2. Removal of the
solvent from the pooled extracts under vacuum
gave 8.3 g of a clear, off-white oil that
distilled at 95-105 °C. at
0.25 mm/
Hg. The 6.5 g of colorless
distillate was
dissolved in 25 mL
IPA, neutralized with concentrated HCl, and then diluted with
anhydrous Et2O to the point of cloudiness. As
crystals formed,
additional
Et2O was added in small increments, allowing clearing
crystallization between each addition. In all, 200 mL
Et2O was used.
After filtering,
Et2O washing, and air drying, there was obtained 6.2 g
of
2,5-dimethoxy-N-
methylamphetamine hydrochloride (METHYL-DMA) as
fine white
crystals with a mp of 117-118 °C. The mixed mp with
2,5-DMA (114-116 °C) was depressed to 96-105 °C. An alternate
synthesis gave the same overall yield of an identical product, but
started with
2,5-DMA. It required two
synthetic steps. The free base
amine was converted to the
crystalline formamide with
formic acid in
benzene using a Dean Stark trap, and this intermediate was reduced to
METHYL-
MDA with LAH.
DOSAGE: above 250 mg.
DURATION: unknown.
QUALITATIVE COMMENTS: (with 250 mg) There is a slight
paresthesia at
about 45 minutes, an awareness on the surface of the skin as if I had
been touched by a cold draft of air. But nothing more. At three
hours, I am completely out, if I was ever in. In the evening I
assayed 120 milligrams of
MDMA, and it barely produced a threshold
effect, so the two materials might be seeing one another.
EXTENSIONS AND COMMENTARY: This is a difficult compound to pin down in
the anthology of drugs. For some reason it has intrigued several
independent, quiet researchers, and I have accumulated a number of
interesting reports over the years. One person told me that he had
felt nothing at up to 60 milligrams. Another had found a threshold at
50 milligrams, and had complete and thorough experiences at both 150
and 200 milligrams. Yet another person described two incidents
involving separate individuals, with intravenous administrations of
0.2 mg/Kg, which would be maybe 15 or 20 milligrams. Both claimed a
real awareness in a matter of minutes, one with a tingling in the
genitalia and the other with a strange presence in the spine. Both
subjects reported increases in body tem
perature and in blood pressure.
Apparently the effects were felt to persist for many hours.
There is an interesting, and potentially informative, convergence of
the
metabolite of one drug with the structure of another. Under
4-MA,
mention was made of a
bronchodilator that has been widely used in the
treatment of asthma and other
allergenic conditions. This compound,
2-methoxy-N-
methylamphetamine is known by the generic name of
methoxyphenamine, and a variety of trade names with Orthoxine (
Upjohn)
being the best known. The typical dosage of
methoxyphenamine is
perhaps 100 milligrams, and it may be used several times a day. It
apparently produces no changes in blood pressure and only a slight
cardiac stimulation. And one of the major
metabolites of it in man is
the
analogue with a
hydroxyl group at the 5-position of the molecule.
This
phenolic amine, 5-hydroxy-2-methoxy-N-
methylamphetamine is just a
methyl group away from METHYL-DMA; it could either be
methylated to
complete the synthesis, or METHYL-DMA could be
demethylated to form
this
phenol. There is plentiful precedent for both of these reactions
occuring in the body. It is always intriguing when drugs which show
distinctly different actions can, in principle, intersect
metabolically at a single structure. One wonders just what the
pharmacology of that common intermediate might be.
Three additional N-
methylated homologues of known
psychedelics warrant
mention, but do not really deserve separate recipes. This is because
they have had only the most cursory assaying, which I have learned
about by personal correspondence. All three were
synthesized by the
reduction of the
formamide of the parent primary
amine with LAH.
METHYL-TMA (or N-
methyl-
3,4,5-trimethoxyamphetamine) had been run up
in several trials to a maximum of 240 milligrams, with some mental
disturbances mentioned only at this highest level. METHYL-TMA-2 (or
N-
methyl-
2,4,5-trimethoxyamphetamine) had been tried at up to 120
milligrams without any effects. METHYL-TMA-6 (or N-
methyl-2,4,6-
trimethoxyamphetamine) had been tried at up to 30 milligrams and it,
too, was apparently without effects. These are reports that I have
heard from others, but I have had no personal experience with them.
Those that I can describe from personal experience are entered
separately as recipes of their own. And there are many, many other
N-
methyl homologues which have been prepared and characterized in the
literature, and have yet to be tasted. So far, however, the only
consistent thing seen is that, with N-
methylation, the potency of the
psychedelics is decreased, but the potency of the stimulants appears
to be pretty much maintained.
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