HPLC Analysis of Stereoisomers of Phenethylamine and its Application to Forensic Toxicology.

本文采用高效液相色谱法（HPLC）同时测定了大鼠尿中甲基苯丙胺（MAMP）、苯丙胺（AMP）、帕拉羟基甲基苯丙胺（MAMP）和帕拉羟基苯丙胺（AMP）的光学异构体（d和1）。经测定为苯甲酰基衍生物。大鼠给药d-或1-异构体（15 mg/kg）后，仅在尿液中发现上述代谢物的d-或1-异构体。外消旋MAMP（15 mg/kg）给药后24小时内，MAMP或AMP的1-异构体的排泄量均小于d-异构体的排泄量（1/d 1.00），而p-OH-MAMP和p-OH-AMP的1-异构体的排泄量大于d-异构体的排泄量（1/d 1.00）。36分钟内的同时分析显示出良好的峰分离度。每种代谢物的1/d比值随时间推移而降低。24小时排泄的d-或1-异构体的总剂量百分比约为给药剂量的50%，<plus-minus>d-异构体为23.70 1.45%，<plus-minus>1-异构体为25.70 1.54%。总1/d比值为1.08 <plus-minus>± 0.03。结果表明，Wistar大鼠体内不存在MAMP的手性异构化酶，并表现出d1的立体选择性代谢。对11份日本吸毒者的MAMP粉末样品和28份日本吸毒者的尿液样品进行了光学异构体分析，从粉末中只检测到d-MAMP，从尿液中分别检测到d-MAMP和d-AMP。这表明人类没有d-MAMP的手性异构化酶。

Simultaneous identification of optical isomers (d and 1) of methamphetamine (MAMP), amphetamine (AMP), para (p) -hydroxy (OH) -MAMP and para (p) -hydroxy (OH) -AMP in rat urine was attempted by high-performance liquid chromatography (HPLC). They were determined as Benzoyl derivatives, After administration of d- or 1-isomer (15mg/kg), only d- or 1-isomers of the above mentioned metabolites were found in rat urine. In rats administered racemic MAMP (15mg/kg), each percent dose of 1-isomers of 1-isomers of MAMP or AMP excreted at four collection time up to 24 hours was less than that of the d-isomer (1/d 1.00), but the doses of 1-isomers of p-OH-MAMP and p-OH-AMP excreted were higher than those of d-isomers (1/d 1.00). Simultaneous analysis within 36 minutes showed good peak resolution. The 1/d ratio for each metabolite decreased with time. The total percent doses of d- or 1-isomer excreted by 24 hours were about 50% of the administered dose, 23.70<plus-minus>1.45% for the d-isomer, 25.70<plus-minus>1.54% for the 1-isomers. The total 1/d ratio was 1.08<plus-minus>0.03. These results indicated that Wistar rats have no chiral isomerization enzyme of MAMP, and show stereoselective metabolism of dlIn the optical isomer analysis of ll MAMP powder samples and 28 human urine specimens obtained from japanese abusers, only d-MAMP was detected from the powder, and d-MAMP and d-AMP were done from urine, respectively. This suggested that humans have no chiral isomerization enzyme of d-MAMP.