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#110 MDMC / EDMA [Note: MDMC is a Shulgin pet name, see commentary below.]


[3D .mol structure]
SYNTHESIS: To a solution of 27.6 g protocatechualdehyde (3,4-dihydroxybenzaldehyde) in 250 mL acetone there was added 57 g finely powdered anhydrous K2CO3 and 43 g 1,2-dibromoethane. The mixture was held at reflux for 16 h, and then the acetone removed by evaporation. The remaining tar-like goo was distributed between equal volumes of H2O and CH2Cl2, and the phases separated by centrifugation. The organic phase was washed with 2x50 mL 5% NaOH, and the solvent removed under vacuum. The residue (22.0 g with the smell of the starting halide) was distilled to give a fraction that boiled at 110 °C at 0.25 mm/Hg to yield 3,4-ethylenedioxybenzaldehyde (1,4-benzodioxane-6-carboxaldehyde) as a white oil weighing 6.88 g. This spontaneously crystallized to give white solids that melted at 50-51 °C.

A solution of 6.64 g 3,4-ethylenedioxybenzaldehyde in 40 mL nitroethane was treated with 0.26 g anhydrous ammonium acetate and held at reflux for 3 days. TLC analysis showed that there was much aldehyde remaining unreacted, so an additional 0.7 g ammonium acetate was added, and the mixture held at reflux for an additional 6 h. The excess nitroethane was removed under vacuum. The residue was dissolved in 30 mL hot MeOH which, with patience and slow cooling, finally deposited a heavy yellow-gold powder. This product 1-(3,4-ethylenedioxyphenyl)-2-nitro-propene melted at 95-96 °C and weighed 6.03 g when air dried to constant weight. Recrystallization from either MeOH or EtOAc gave the product as a yellow solid, but without any improvement in mp.

A solution of 4.0 g of 1-(3,4-ethylenedioxyphenyl)-2-nitropropene was made in 30 mL warm acetic acid. This was added to a suspension of 16 g elemental electrolytic iron in 75 mL acetic acid. The mixture was heated on the steam bath, and an exothermic reaction set in at about 70 °C. Heating was continued and the reaction allowed to proceed until the mass was a thick gray color and a dirty scum had been formed on the surface. After about 2 h, the entire mix was poured into 2 L H2O and filtered free of a little residual unreacted iron which was washed with CH2Cl2. The filtrate and washes were extracted with 3x100 mL CH2Cl2 and the pooled organic extracts washed with 2x50 mL 5% NaOH. Removal of the solvent gave 3.38 g of an amber oil which was distilled. The product 1-(3,4-ethylenedioxyphenyl)-2-propanone distilled as a white oil, at 105-110 °C at 0.2 mm/Hg. It weighed 2.74 g.

To 2.0 g. of 1 inch squares of light-weight aluminum foil there was added a solution of 50 mg mercuric chloride in 70 mL water. After standing at room temperature for 30 min, the H2O was drained away, and the amalgamated aluminum washed twice with H2O, and shaken as dry as possible. There was then added, promptly and in immediate sequence, a solution of 3 g methylamine hydrochloride in 3 mL H2O, 9 mL IPA, 7.25 mL 25% NaOH, 2.70 g of 1-(3,4-ethylenedioxyphenyl)-2-propanone, and 18 mL IPA. The mixture was heated on the steam bath until an exothermic reaction set in, and then it was continuously swirled as the reaction proceeded. When the aluminum was consumed, there was a colorless gray sludge, and this was filtered and washed with 2x10 mL MeOH. The combined mother liquors and washes were stripped of solvent under vacuum. The two phase residue was suspended in 400 mL H2O containing sufficient H2SO4 to make the resulting water solution acidic to pH paper. This was washed with 3x50 mL CH2Cl2, made basic with 25% NaOH, and the product extracted with 3x50 mL CH2Cl2. The resulting 3.01 g slightly amber residue oil was distilled at 110-120 °C at 0.25 mm/Hg to give 2.53 g of a white oil, which did not appear to absorb carbon dioxide. This was dissolved in 12 mL IPA, neutralized with 1 mL concentrated HCl and diluted with anhydrous Et2O to the point of initial turbidity. There separated white crystals of 3,4-ethylenedioxy-N-methylamphetamine hydrochloride (MDMC) which weighed, when air dried to constant weight, 2.53 g.

DOSAGE: 200 or more mg.

DURATION: 3 - 5 h.

QUALITATIVE COMMENTS: (with 150 mg) A flood of paresthesia at the 30 minute point, and then nothing. There was the development of a plus one-and-a half effect over the next hour with the tendency to drift into a dozing state with hypnogogic imagery. There were colored letters in the periphery of my visual field. There was no appetite loss nor was there any blood pressure rise. And no eye jiggle or teeth clenching. I was out of the experience in 4 to 5 hours. A repeat of this level a few days later gave a bare possible threshold with no other effects.

(with 200 mg) There was something unmistakable at 45 minutes, with hints of nystagmus. Possibly MDMA-like, with no indicators of anything psychedelic. Subtle return to baseline, and there were no after-effects.

(with 250 mg) Alert at 40 minutes, and to a clear ++ at an hour. Slight something in the eye muscles. Dropping thirty minutes later, and baseline at three hours.

(with 250 mg) I am at a bare threshold at best.

EXTENSIONS AND COMMENTARY: What a strange and completely unsatisfactory compound! In the original run-up from low levels to increasing higher levels, there never was a dosage that was a minus, that had no effect. At every level, something was thought to be there, usually at a level of a single plus or thereabouts. But with different people, different responses. There is no way of guessing what an active level might be, or how consistent that level might be between different people, or for that matter what the responses are that might be expected at that level.

This was yet one more effort to find an MDMA-like substitute by the miniscule manipulation of the MDMA molecule. Perhaps a small molecular change might leave the particular magic of the MDMA action alone, but eliminate the serotonin neuron problem in test animals. Maybe the serotonin neuron change is essential for MDMA to have the action it has. Who can tell?

The original name that this compound got, during the several explorations of MDMA analogues, was based on the nickname for MDMA which was Adam. HAD'EM was mentioned with the hydroxy compound, MADAM with the 6-methyl homologue, and FLADAM with the 6-fluoro analogue. This compound got the sobriquet MACADAM from that horrible black gooey mess generated at the aldehyde stage. This was shortened to RCS and eventually the RCS was added to the MDMA parent name. Thus, MDMC. It doesn't really make sense; EDMA is more reasonable. But then there is no reason why MDMC should make sense.

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