Distribution of 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) stereoisomers in a fatal poisoning

Forensic Sci Int. 1996 Dec 2;83(2):111-9. doi: 10.1016/s0379-0738(96)02025-7.


This communication presents the quantitation and differential distribution of the enantiomers of 3,4-methylenedioxymethamphetamine (MDMA) and its physiologically active metabolite 3,4-methylenedioxyamphetamine (MDA) in a fatal poisoning following insufflation of MDMA, cocaine and heroin. Animal studies have demonstrated the stereoselective pharmacokinetics and neurotoxicity of these compounds; however, enantiomeric distributions have not been reported in humans. Quantitation of MDMA and MDA enantiomer was by gas chromatography/mass spectrometry (GC/MS) following chiral derivatization with N-trifluoroacetyl-L-triproyl chloride (LTPC). The decedents' blood concentration of S(+)-MDMA was slightly less than that of R(-)-MDMA (1.3 vs. 1.6 mg/l, respectively), while the S(+)- and R(-)-MDA blood concentrations were identical (0.8 mg/l). Both primary routes of excretion, bile and urine, had greater concentrations of R(-)-MDMA than the S(+) isomer. These fluids also contained twice the concentration of S(+)-MDA than the R(-)-isomer. These data indicate that S(+)-MDMA is metabolized and eliminated faster than R(-)-MDMA. The results appear to support the findings in animals regarding stereoselective metabolism of MDMA.

Publication types

  • Case Reports
  • Review

MeSH terms

  • 3,4-Methylenedioxyamphetamine / pharmacokinetics
  • Adult
  • Cocaine / poisoning
  • Fatal Outcome
  • Gas Chromatography-Mass Spectrometry
  • Heroin / poisoning
  • Humans
  • Male
  • N-Methyl-3,4-methylenedioxyamphetamine / blood
  • N-Methyl-3,4-methylenedioxyamphetamine / pharmacokinetics*
  • N-Methyl-3,4-methylenedioxyamphetamine / poisoning*
  • Narcotics / poisoning
  • Stereoisomerism
  • Tissue Distribution


  • Narcotics
  • 3,4-Methylenedioxyamphetamine
  • Heroin
  • Cocaine
  • N-Methyl-3,4-methylenedioxyamphetamine