Published: Journal of Analytical Toxicology, Volume 24, Number 2, March, pp.140-145

Interpretation and Enantiomer Analysis of Methamphetamine Abusers’ Urine and Illegally Brewed Methamphetamine Crystals
Toshiaki Nagai¹, Kazumi Matsushima^1,2, Tatsuo Nagai³, Yuko Yanagisawa³, Akihiko Fujita⁴, Akira Kurosu¹, and Shogo Tokudome¹

¹Department of Legal Medicine, Dokkyo University of School of Medicine, 880, Kitakobayashi, Mibu, 321-0293 Tochigi, Japan; ²Scientific Crime Detection Laboratory, Tochigi Prefectural Police Headquarters, 1-1-20, Hanawada, Utsunomiyama, 320-8510 Tochigi, Japan; ³Department of Forensic Medicine and Science, Kitasato University Graduate School of Medicine 1-15-1, Kitasato, Sagamihara-shi, 228-8555 Kanagawa, Japan; and ⁴Second Department of Anesthesiology, Dokkyo University School of Medicine, 880, Kitakobayashi, Mibu, 321-0293 Tochigi, Japan

This study deals with the high-performance liquid chromatographic identification of methamphetamine (MAMP) and amphetamine (AMP) enantiomers (d- and l-forms) in five illicit MAMP crystals and in urine specimens from 30 Japanese MAMP abusers. The analysis revealed that two of the types of crystals have a different optical purity ratio (l/d) and the other three have a single crystal of either the d- or l-enantiomer. The l/d ratios of two types of crystals were 0.04 and 49.4, and no racemic form (l/d = 1.00) was found. The urinary analysis showed that nonmetabolized MAMP and its demethylated metabolite, AMP, were present in urine specimens of all addicts. The stereoisomeric profiles in urine can be classified roughly into five groups according to the detected amount and the l/d ratio of MAMP and AMP enantiomers collected at one time point. In the first group, only d-MAMP and d-AMP were detected (in 16 cases). In the second group, only l-MAMP and l-AMP were detected (in one case). In the third group, the amount of the l-enantiomer detected, for both MAMP and AMP, was less than that of the d-enantiomer, and the l/d ratio was between 0.004 and 0.54 for MAMP and between 0.01 and 0.07 for AMP (in five cases). In the fourth group, the l-enantiomer of MAMP and AMP was found to be more abundant than the d-enantiomer, and the l/d ratio was between 2.63 and 30.11 for MAMP and between 1.23 and 31.30 for AMP (in four cases). In the fifth group, the amount of l-MAMP detected was greater than that of d-MAMP, and less l-AMP than d-AMP was detected. The l/d ratios were between 1.13 and 8.82 for MAMP and between 0.17 and 0.82 for AMP (in four cases). These results might be suitable for identification and the forensic toxicological investigation of AMP analogues.

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