title: Distribution of 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) stereoisomers in a fatal poisoning.
abstract: 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.
authors.affiliation: Department of Pathology, Medical College of Virginia, Virginia 23298-0165, USA.
authors.forename: K A
authors.initials: KA
authors.lastname: Moore
authors.forename: A
authors.initials: A
authors.lastname: Mozayani
authors.forename: M F
authors.initials: MF
authors.lastname: Fierro
authors.forename: A
authors.initials: A
authors.lastname: Poklis
mesh_terms: D015104:3,4-Methylenedioxyamphetamine / Q000493:pharmacokinetics; D000328:Adult; D003042:Cocaine / Q000506:poisoning; D017809:Fatal Outcome; D008401:Gas Chromatography-Mass Spectrometry; D003932:Heroin / Q000506:poisoning; D006801:Humans; D008297:Male; D018817:N-Methyl-3,4-methylenedioxyamphetamine / Q000097:blood / Q000493:pharmacokinetics* / Q000506:poisoning*; D009294:Narcotics / Q000506:poisoning; D013237:Stereoisomerism; D014018:Tissue Distribution
chemical_list: D009294:Narcotics; D015104:3,4-Methylenedioxyamphetamine; D003932:Heroin; D003042:Cocaine; D018817:N-Methyl-3,4-methylenedioxyamphetamine