Moore K A, Mozayani A, Fierro M F, Poklis A
Department of Pathology, Medical College of Virginia, Virginia 23298-0165, USA.
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.
本报告介绍了在吸入摇头丸（MDMA）、可卡因和海洛因后发生的致命中毒事件中，3,4-亚甲基二氧基甲基苯丙胺（MDMA）及其生理活性代谢物3,4-亚甲基二氧基苯丙胺（MDA）对映体的定量及差异分布情况。动物研究已证明这些化合物具有立体选择性药代动力学和神经毒性；然而，人体中的对映体分布情况尚未见报道。MDMA和MDA对映体的定量分析采用气相色谱/质谱联用（GC/MS）法，先用N-三氟乙酰-L-三丙酰氯（LTPC）进行手性衍生化。死者血液中S(+)-MDMA的浓度略低于R(-)-MDMA（分别为1.3毫克/升和1.6毫克/升），而S(+)-和R(-)-MDA的血液浓度相同（0.8毫克/升）。排泄的主要途径胆汁和尿液中，R(-)-MDMA的浓度均高于S(+)异构体。这些液体中S(+)-MDA的浓度也是R(-)-异构体的两倍。这些数据表明，S(+)-MDMA的代谢和消除速度比R(-)-MDMA快。结果似乎支持了动物研究中关于MDMA立体选择性代谢的发现。
