PMID- 9022274 OWN - NLM STAT- MEDLINE DCOM- 19970304 LR - 20190831 IS - 0379-0738 (Print) IS - 0379-0738 (Linking) VI - 83 IP - 2 DP - 1996 Dec 2 TI - Distribution of 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) stereoisomers in a fatal poisoning. PG - 111-9 AB - 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. FAU - Moore, K A AU - Moore KA AD - Department of Pathology, Medical College of Virginia, Virginia 23298-0165, USA. FAU - Mozayani, A AU - Mozayani A FAU - Fierro, M F AU - Fierro MF FAU - Poklis, A AU - Poklis A LA - eng PT - Case Reports PT - Journal Article PT - Review PL - Ireland TA - Forensic Sci Int JT - Forensic science international JID - 7902034 RN - 0 (Narcotics) RN - 4764-17-4 (3,4-Methylenedioxyamphetamine) RN - 70D95007SX (Heroin) RN - I5Y540LHVR (Cocaine) RN - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine) SB - IM MH - 3,4-Methylenedioxyamphetamine/pharmacokinetics MH - Adult MH - Cocaine/poisoning MH - Fatal Outcome MH - Gas Chromatography-Mass Spectrometry MH - Heroin/poisoning MH - Humans MH - Male MH - N-Methyl-3,4-methylenedioxyamphetamine/blood/*pharmacokinetics/*poisoning MH - Narcotics/poisoning MH - Stereoisomerism MH - Tissue Distribution RF - 28 EDAT- 1996/12/02 00:00 MHDA- 1996/12/02 00:01 CRDT- 1996/12/02 00:00 PHST- 1996/12/02 00:00 [pubmed] PHST- 1996/12/02 00:01 [medline] PHST- 1996/12/02 00:00 [entrez] AID - S0379-0738(96)02025-7 [pii] AID - 10.1016/s0379-0738(96)02025-7 [doi] PST - ppublish SO - Forensic Sci Int. 1996 Dec 2;83(2):111-9. doi: 10.1016/s0379-0738(96)02025-7.