Enantio-selective cognitive and brain activation effects of N-ethyl-3,4-methylenedioxyamphetamine in humans

Neuropharmacology. 2001 Aug;41(2):263-71. doi: 10.1016/s0028-3908(01)00060-0.


In a randomised double-blind trial the subjective, neuropsychological and brain activation effects of the two enantiomers of the MDMA (ecstasy-) like drug N-ethyl-3,4-methylenedioxyamphetamine (MDE) were studied in five normal subjects using functional magnetic resonance imaging (fMRI). (S)-MDE produced elevated mood, impairments in conceptually driven cognition and marked right frontal activation. In contrast, (R)-MDE produced increased depression, enhanced visual feature processing, and activation of visual cortical and left frontal areas. Plasma concentrations were higher for the (R)-enantiomer. The so-called entactogenic effects of MDE are likely to be caused by the (S)-enantiomer, whereas (R)-MDE appears to be responsible for neurotoxic effects.

Publication types

  • Clinical Trial
  • Randomized Controlled Trial

MeSH terms

  • 3,4-Methylenedioxyamphetamine / analogs & derivatives*
  • 3,4-Methylenedioxyamphetamine / blood
  • 3,4-Methylenedioxyamphetamine / pharmacology*
  • Analysis of Variance
  • Brain / drug effects*
  • Brain / physiology
  • Cognition / drug effects*
  • Cognition / physiology
  • Double-Blind Method
  • Humans
  • Magnetic Resonance Imaging / methods
  • Male
  • Neuropsychological Tests*
  • Psychometrics
  • Statistics, Nonparametric
  • Stereoisomerism


  • 3,4-Methylenedioxyamphetamine
  • 3,4-methylenedioxyethamphetamine