#131 METHYL-MMDA-2 SYNTHESIS: 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 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 3×100 mL CH2Cl2. All organics were combined, washed with 2×75 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 cyanoborohydride. 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 3×100 mL CH2Cl2, and the pooled extracts were, in turn, extracted with 2×100 mL dilute H2SO4. This aqueous phase was washed with CH2Cl2, made basic with NaOH, and extracted with 3×100 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.
DOSAGE: greater than 70 mg.
DURATION: unknown.
QUALITATIVE COMMENTS: (with 70 mg) “Maybe a threshold—pleasant but not possible to characterize it.”
EXTENSIONS AND COMMENTARY: 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 analogue that has been explored as an N-methyl derivative. A more highly substituted analogue has also been made, the N-methyl derivative of . (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 ) 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.
13 May 2016 · Creative Commons BY-NC-SA ·

About PiHKAL · info

This version of Book II of PiHKAL is based on the Erowid online version, originally transcribed by Simson Garfinkle and converted into HTML by Lamont Granquist. I drew also on “Tyrone Slothrop’s” (Unfinished) Review of PIHKAL to enumerate the many analogues mentioned in PiHKAL but not described at length. Many, many others have since been added.
I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore the typographic niceties found in the printed edition. I’ve also made minor changes to some chemical names in line with current nomenclature practice. Typically the change is little more than expanding a prefix or setting it in italics. The history page has further details.

Cautionary note

“At the present time, restrictive laws are in force in the United States and it is very difficult for researchers to abide by the regulations which govern efforts to obtain legal approval to do work with these compounds in human beings.
“No one who is lacking legal authorization should attempt the synthesis of any of the compounds described in these files, with the intent to give them to man. To do so is to risk legal action which might lead to the tragic ruination of a life. It should also be noted that any person anywhere who experiments on himself, or on another human being, with any of the drugs described herein, without being familiar with that drug’s action and aware of the physical and/or mental disturbance or harm it might cause, is acting irresponsibly and immorally, whether or not he is doing so within the bounds of the law.”
Alexander T. Shulgin

Copyright notice

The copyright for Book I of PiHKAL has been reserved in all forms and it may not be distributed. Book II of PiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.

Ordering information

PiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of phenethylamines. This book belongs in the library of anyone seeking a rational, enlightened and candid perspective on psychedelic drugs.
Though Sasha and Ann have put Book II of PiHKAL in the public domain, available to anyone, I strongly encourage you to buy a copy. We owe them — and there’s still nothing quite like holding a real book in your hands.
PiHKAL (ISBN 0-9630096-0-5) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.
Transform Press,
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Berkeley, CA 94701

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