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Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors.

Alexander M SherwoodElise K BurkhartzmeyerSamuel E WilliamsonMichael T Faley
Published in: ACS omega (2023)
A divergent two-step process has provided access to optically pure enantiomers of MDMA and MDA, clinically relevant phenylisopropylamine entactogens. Target compounds were synthesized from commercially available alanine-derived aziridines. Critical process parameters were identified, and the reactions were optimized to avoid chromatographic purifications toward gram-scale isolations, providing ( R )-(-)-MDMA, ( S )-(+)-MDMA, ( R )-(-)-MDA, and ( S )-(+)-MDA each in greater than 98% purity by UPLC, >99% enantiomeric excess, and net yields between 50 and 60% for the complete process.
Keyphrases
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  • capillary electrophoresis
  • cell cycle arrest
  • simultaneous determination
  • mass spectrometry
  • gram negative
  • cell death
  • multidrug resistant