SYNTHESIS: To a well stirred solution of 9.7 g dimethylamine
hydrochloride in 50 mL MeOH there was added 3.56 g of
3,4-methylenedioxyphenylacetone (see under MDMA for its preparation)
followed by 0.88 g sodium cyanoborohydride. A 1:1 mixture of
concentrated HCl and MeOH was added as required to maintain the pH at
about 6 as determined with external, dampened universal paper. Twenty
drops were called for over the first four h, and a total of 60 drops
were added over the course of two days at which time the reduction was
complete. After the evaporation of most of the MeOH solvent, the
reaction mixture was added to 250 mL H2O and made strongly acidic with
an excess of HCl. After washing with 2x100 mL CH2Cl2 the aqueous
phase was made basic with 25% NaOH, and extracted with 3x100 mL
CH2Cl2. Removal of the solvent under vacuum yielded a nearly
colorless oil that was distilled at 85-90 °C at 0.3 mm/Hg. There was
obtained 1.5 g of a water-white oil that was dissolved in 8 mL IPA,
neutralized with concentrated HCl and then diluted with 10 mL
anhydrous Et2O. The slightly turbid solution deposited a light lower
oily layer which slowly crystallized on scratching. With patience, an
additional 75 mL of Et2O was added, allowing the formation of a white
crystalline mass. This was removed by filtration and washed with
additional Et2O. After air drying there was obtained 1.3 g of
3,4-methylenedioxy-N,N-dimethylamphetamine hydrochloride (MDDM) with a
mp of 172-173 °C. The NMR spectrum (60 mH) of the hydrochloride salt
(in D2O and with external TMS) was completely compatible with the
expected structure. The signals were: 1.25, 1.37 (d) CCH3, 3H; ArCH2
under the N(CH3)2, 2.96, 8H; CH (m) 3.65; CH2O2 (s) 6.03 2H; ArH 6.93
(3H). Anal: (C12H18ClNO2) N.
DOSAGE: greater than 150 mg.
DURATION: unknown.
QUALITATIVE COMMENTS: (with 150 mg) No effects whatsoever.
(with 150 mg) The effects, if any, were so-so. Perhaps a threshold.
But my libido was non-existent for three days.
(with 550 mg) I took 550 milligrams of it Saturday night and I had a
pretty bad trip. On a scale of positive 10 to negative 10 it was
about a negative 6. It really downed me. Two other friends took 200
milligrams. They found it very pleasant after about 20 minutes. It
was a plus 3 [on the -10 to +10 scale]. Then it wore off a little
bit; and then, 4 hours later, it hit them even stronger and was about
a plus 5.
(with 1000 mg) I took up to a gram of it and absolutely nothing.
EXTENSIONS AND COMMENTARY: I cannot attest for the actual drug that
had been used in the two larger-dose reports above. These are from an
anonymous source associated with clandestine syntheses. If this
material does eventually prove to be active, it is going to require a
pretty hefty dose. But it may well have some activity, as there have
been reports in the forensic literature of its preparation, or at
least its intended preparation, in illicit laboratories. It seems
unlikely that much effort would be directed towards the synthesis of a
completely inactive compound.
The reduced potency of MDDM has been exploited in an unexpected way.
Based on the premise that the dialkylation of the amine group of
amphetamine makes the parent compound intrinsically less active but
without interfering with its ability to enter the brain, a large
number of materials have been explored to take advantage of this very
property. There is a need in medical diagnosis for agents that can
allow various organs of the body to be visualized. One of the most
powerful modalities for this work is the positron camera, and the use
of the unusual properties of the positron that allow it to work. In
the art of positron emission tomography (PET), an emitted positron
(from a radioactive and thus unstable atom) will quickly interact with
a nearby electron and all mass disappears with the complete conversion
to energy. The detection of the produced pair of annihilation gamma
rays will establish with great exactness the line along which this
interaction occurred. So if one were to put an unstable atom into a
compound that went to the tissue of the brain, and this atom were to
decay there, the resulting gamma rays would allow a "photograph" to be
made of the brain tissue. One could in this way visualize brain
tissue, and observe abnormalities.
But what is needed is a molecule that carries the unstable atom (and
specifically one that emits positrons) and one which goes to the brain
as well. One of the very best unstable atoms for the formation of
positrons is iodine, where there is an isotope of mass 122 which is
perfect for these needs. And, of course, the world of the psychedelic
drugs is tailor-made to provide compounds that go to the brain. But,
the last thing that the physician wants, with the diagnostic use of
such tools, would be to have the patient bouncing around in some
turned-on altered state of consciousness.
So the completely logical union of these requirements is to take a
compound such as DOI (carrying the needed atom and certainly going to
the brain) and put two methyl groups on the nitrogen (which should
reduce the chances for conspicuous biological activity). This
compound was made, and it does label the brain, and it has shown
promise as a flow indicator in the brain, and it and several of its
close relatives are discussed in their own separate recipe, called
IDNNA.
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