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#105 MDDM


[3D .mol structure]
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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