MDMA
Chemistry
- 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 at Merck as a synthetic intermediate; never tested for psychoactivity.
- Alexander "Sasha" Shulgin — popularised it, 1976
Resynthesized it after a student described the effects, then introduced it to the psychologist Leo Zeff, who brought it to psychotherapy.
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