CH₃CH₃

MDMA

Chemistry

29 atoms · Conformer computed and published by PubChem.
Formula
C11H15NO2
Molar mass
193.24 g/mol
IUPAC name
1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
InChIKey
SHXWCVYOXRDMCX-UHFFFAOYSA-N

Chemistry from PubChem CID 1615.

Also known as

  • Ecstasy
  • 3,4-methylenedioxymethamphetamine
  • Midomafetamine
  • 42542-10-9
  • Methylenedioxymethamphetamine
  • DL-(3,4-Methylenedioxy)methamphetamine
  • N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE
  • (RS)-3,4-(methylenedioxy)methamphetamine

Stereoisomers

2 distinct stereoisomers are registered for this structure. This area's record is the racemate — the mixture, which is normally the form encountered.

  • Racemic MDMA this area mixture CID 1615

    What is actually sold and taken.

  • (R)-(−)-MDMA CID 667458

    More of the psychedelic-leaning character.

  • (S)-(+)-MDMA CID 854031

    More of the stimulant character.

Sold and taken as the racemate; essentially nobody encounters a single enantiomer. The two differ in character — (S)-MDMA carries more of the stimulant action, (R)-MDMA more of the psychedelic-leaning effect — but since the mixture is what exists in practice, that distinction is chemistry rather than something to plan around.

Attribution

  • Anton Köllisch — first synthesis, 1912

    Made as a chemical intermediate on the way to methylhydrastinine, not as a drug candidate; described without a name in Merck patent DE 274350 C (filed 24 Dec 1912, published 16 May 1914). The long-repeated story that Merck was chasing an appetite suppressant is false — Freudenmann et al. traced it to uncritical repetition of secondary sources.

    source

  • Portrait of Alexander "Sasha" Shulgin
    Alexander "Sasha" Shulgin — popularised it, 1976

    NOT his synthesis: first made by Anton Köllisch at Merck in 1912 (patented 1913). Shulgin re-synthesized it, developed a new synthesis route, and in 1976 introduced it to the Oakland psychologist Leo Zeff, through whom it spread to therapists; he co-published the first human pharmacology with David Nichols in 1978.

    source

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