modified on 6 April 2009 at 13:32 ••• 3,009 views


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A suspension of 17.4 g electrolytic elemental iron in 100 g glacial acetic acid was heated on the steam-bath until there were the first signs of bubbling and reaction, about 60 °C. There was then added, in small portions, a suspension of 9.2 g 1-(2-methoxy-4,5-methylenedioxyphenyl)-2-nitropropene (see under MMDA-2 for its preparation) in 40 g warm glacial acetic acid. The reaction was extremely exothermic. After the color had lightened as much as possible, there was added an additional quantity of iron sufficient to completely discharge the residual yellow color. Mechanical stirring was maintained as the reaction mixture was allowed to return to room temperature. All was poured into 800 mL H2O, and the insolubles were removed by filtration. These were washed alternately with H2O and with CH2Cl2, the combined filtrate and washes were separated, and the aqueous phase extracted with 3x100 mL CH2Cl2. All organics were combined, washed with 2x75 mL 5% NaOH (which removed most of the color) and the solvent removed under vacuum. The 8.7 g residue was distilled at 90-105 °C at 0.2 mm/Hg to give 6.7 g of 2-methoxy-4,5-methylenedioxyphenylacetone as a pale yellow oil.

To a magnetically stirred solution of 30 g methylamine hydrochloride in 150 mL warm MeOH, there was added 6.5 g 2-methoxy-4,5-methylenedioxyphenylacetone followed by 3.0 g sodium cyano-borohydride. Concentrated HCl was added as was required to keep the mixture at a pH of about 6. When the reaction was complete, it was added to 1 L H2O and made strongly basic with 25% NaOH. This was extracted with 3x100 mL CH2Cl2, and the pooled extracts were, in turn, extracted with 2x100 mL dilute H2SO4. This aqueous phase was washed with CH2Cl2, made basic with NaOH, and extracted with 3x100 mL CH2Cl2. Removal of the solvent from these pooled extracts under vacuum gave 8.7 g of an amber oil. This was distilled at 110-125 °C at 0.25 mm/Hg to give 5.1 g of a colorless oil. This was dissolved in 30 mL IPA, neutralized with about 3 mL concentrated HCl, and diluted with 60 mL anhydrous Et2O. The clear solution slowly deposited white crystals which were removed by filtration and air dried to give 4.2 g 2-methoxy-N-methyl-4,5-methylenedioxyamphetamine hydrochloride (METHYL-MMDA-2) with a mp of 168-169 °C. Anal. (C12H18ClNO3) C,H.


greater than 70 mg.




(with 70 mg) Maybe a threshold--pleasant but not possible to characterize it.


With the effective dosage of the unmethylated homologue being the range of 25 to 50 milligrams, this N-methyl compound is, as with the other N-methylated materials discussed here, again of reduced activity. The highest dose yet reported was 70 milligrams, and there is no way of estimating what miight be an active level nor, once there, what the quality of the effects might be.

This is the only MMDA analogue that has been explored as an N-methyl derivative. A more highly substituted analogue has also been made, the N-methyl derivative of DMMDA. Isoapiole (see its preparation under DMMDA) was oxidized with formic acid and hydrogen peroxide to the ketone (2,5-dimethoxy-3,4-methylenedioxyphenylacetone, a solid with a mp of 75-76 °C from methanol) which was reductively aminated with methylamine and amalgamated aluminum to give 2,5-dimethoxy-N-methyl-3,4-methylenedioxyamphetamine hydrobromide monohydrate (METHYL-DMMDA, or DMMDMA) as a white crystalline solid with a mp of 91-92 °C. The hydrochloride salt was a hygroscopic solid. Anal. (C13H22BrNO5) C,H. The above ketone has also been used in the synthesis of another methylated DMMDA, on the beta-carbon. This is described under DMMDA itself. DMMDMA has not yet been launched into an evaluation program, and I wouldn't be surprised if the needed dosage might be up there somewhere over 100 milligrams. I feel quite sure that the answers may be known in the near future. There is a surprisingly large number of inconspicuous chemical explorers out there all over the world, doing their synthetic thing in their private laboratories. They are truly the astronauts of inner space.