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[Identification of optical isomers of methamphetamine and its application to forensic medicine].
Nihon Hoigaku Zasshi. 1992 Aug; 46(4):244-53.NH

Abstract

In order to identify optical isomers (d and l-) of methamphetamine (MAMP), GC-MS analysis using optically resolvable reagent of N-trifluoroacetyl-L-prolyl chloride (L-TPC) and HPLC analysis using chiral cellulose-based columns were compared. In analysis of d- or l-MAMP (M) of TPC (T) derivatives by the GC-MS, contrary to the expectation that only d(M)-L(T) or l(M)-L(T) could be detected chemically, two diastereomers of d(M)-L(T) and d(M)-D(T) for d-MAMP and two of l(M)-L(T) and l(M)-D(T) for l-MAMP were demonstrated respectively. This results was attributed to a small percentage of D-TPC present in L-TPC. For racemic (dl)-MAMP, none of these four isomers could be individually isolated, and they were detected as two overlapping peaks. In the HPLC analysis using chiral columns, d- and l-isomers of MAMP and amphetamine (AMP) could be clearly isolated with merely one analytical procedure, and the l/d ratio was possible to calculate with facility. From the rats urine administered d- or l-MAMP, only the corresponded optically active form of the administered drug was detected, and when racemic (dl)-MAMP was administered, d-MAMP, l-MAMP and their metabolites AMP were distinctly detected. The l/d ratio calculated from amount of MAMP and AMP excreted in rat urine within 24 hr was not in accordance with that of the administered dl-MAMP (l/d = 1.01): the l/d ratio was 0.45 for MAMP and 0.58 for AMP, and 0.50 for the total of MAMP and AMP. The similar results were observed in case of racemic (dl)-AMP. From several human specimens obtained from the cadavers dead by MAMP poisoning, only d-MAMP and the metabolite d-AMP were detected, and neither l-MAMP or l-AMP were demonstrated. In particular, a high concentration of d-MAMP was detected in gastric contents, brain, lung and liver. From the MAMP powder in possession, only d-MAMP was detected. These results suggest that this chiral column-HPLC procedure could be applied to medicolegal practice and forensic scientific investigation.

Authors+Show Affiliations

Department of Legal Medicine, Dokkyo University School of Medicine, Tochigi, Japan.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

English Abstract
Journal Article

Language

jpn

PubMed ID

1405017

Citation

Nagai, T, et al. "[Identification of Optical Isomers of Methamphetamine and Its Application to Forensic Medicine]." Nihon Hoigaku Zasshi = the Japanese Journal of Legal Medicine, vol. 46, no. 4, 1992, pp. 244-53.
Nagai T, Kamiyama S, Kurosu A, et al. [Identification of optical isomers of methamphetamine and its application to forensic medicine]. Nihon Hoigaku Zasshi. 1992;46(4):244-53.
Nagai, T., Kamiyama, S., Kurosu, A., & Iwamoto, F. (1992). [Identification of optical isomers of methamphetamine and its application to forensic medicine]. Nihon Hoigaku Zasshi = the Japanese Journal of Legal Medicine, 46(4), 244-53.
Nagai T, et al. [Identification of Optical Isomers of Methamphetamine and Its Application to Forensic Medicine]. Nihon Hoigaku Zasshi. 1992;46(4):244-53. PubMed PMID: 1405017.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - [Identification of optical isomers of methamphetamine and its application to forensic medicine]. AU - Nagai,T, AU - Kamiyama,S, AU - Kurosu,A, AU - Iwamoto,F, PY - 1992/8/1/pubmed PY - 1992/8/1/medline PY - 1992/8/1/entrez SP - 244 EP - 53 JF - Nihon hoigaku zasshi = The Japanese journal of legal medicine JO - Nihon Hoigaku Zasshi VL - 46 IS - 4 N2 - In order to identify optical isomers (d and l-) of methamphetamine (MAMP), GC-MS analysis using optically resolvable reagent of N-trifluoroacetyl-L-prolyl chloride (L-TPC) and HPLC analysis using chiral cellulose-based columns were compared. In analysis of d- or l-MAMP (M) of TPC (T) derivatives by the GC-MS, contrary to the expectation that only d(M)-L(T) or l(M)-L(T) could be detected chemically, two diastereomers of d(M)-L(T) and d(M)-D(T) for d-MAMP and two of l(M)-L(T) and l(M)-D(T) for l-MAMP were demonstrated respectively. This results was attributed to a small percentage of D-TPC present in L-TPC. For racemic (dl)-MAMP, none of these four isomers could be individually isolated, and they were detected as two overlapping peaks. In the HPLC analysis using chiral columns, d- and l-isomers of MAMP and amphetamine (AMP) could be clearly isolated with merely one analytical procedure, and the l/d ratio was possible to calculate with facility. From the rats urine administered d- or l-MAMP, only the corresponded optically active form of the administered drug was detected, and when racemic (dl)-MAMP was administered, d-MAMP, l-MAMP and their metabolites AMP were distinctly detected. The l/d ratio calculated from amount of MAMP and AMP excreted in rat urine within 24 hr was not in accordance with that of the administered dl-MAMP (l/d = 1.01): the l/d ratio was 0.45 for MAMP and 0.58 for AMP, and 0.50 for the total of MAMP and AMP. The similar results were observed in case of racemic (dl)-AMP. From several human specimens obtained from the cadavers dead by MAMP poisoning, only d-MAMP and the metabolite d-AMP were detected, and neither l-MAMP or l-AMP were demonstrated. In particular, a high concentration of d-MAMP was detected in gastric contents, brain, lung and liver. From the MAMP powder in possession, only d-MAMP was detected. These results suggest that this chiral column-HPLC procedure could be applied to medicolegal practice and forensic scientific investigation. SN - 0047-1887 UR - https://www.unboundmedicine.com/medline/citation/1405017/[Identification_of_optical_isomers_of_methamphetamine_and_its_application_to_forensic_medicine]_ L2 - https://medlineplus.gov/methamphetamine.html DB - PRIME DP - Unbound Medicine ER -