CH₃CH₃

MDA

Chemistry

26 atoms · Conformer computed and published by PubChem.
Formula
C10H13NO2
Molar mass
179.22 g/mol
IUPAC name
1-(1,3-benzodioxol-5-yl)propan-2-amine
InChIKey
NGBBVGZWCFBOGO-UHFFFAOYSA-N

Chemistry from PubChem CID 1614.

Also known as

  • Tenamfetamine
  • 3,4-methylenedioxyamphetamine
  • Methylenedioxyamphetamine
  • 4764-17-4
  • Tenamfetaminum
  • Love
  • methylene dioxyamphetamine
  • 1,3-Benzodioxole-5-ethanamine, alpha-methyl-

Stereoisomers

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

  • 3,4-Methylenedioxyamphetamine this area mixture CID 1614
  • (-)-3,4-(Methylenedioxy)amphetamine CID 3046161
  • (+)-3,4-(Methylenedioxy)amphetamine CID 3050061

Encountered as the racemate. As with MDMA the enantiomers differ in character, the (S) form being more stimulant-like, but single-enantiomer MDA is not something that circulates.

Attribution

  • Gordon Alles — discovered its activity, 1930

    MDA was first synthesised by Carl Mannich and Willy Jacobsohn in 1910. Alles took 126 mg orally and produced the first description of the drug's psychoactive effects, but did not publish it until 1959, in 'Some Relations Between Chemical Structure and Physiological Action of Mescaline and Related Compounds' in Neuropharmacology: Transactions of the Fourth Conference (Josiah Macy Jr. Foundation). Wikipedia and most secondary accounts date the self-experiment to July 1930; Passie and Benzenhofer (2018), reading Alles's own 1959 text, date it to 1934 and describe the dose as accidental. The event and the 126 mg are well attested; the year is not settled.

    source

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