Direct analysis of conjugate metabolites of methamphetamine, 3,4-methylenedioxymethamphetamine, and their designer drugs in biological fluids

Journal of Health Science

Volumn 55, Issue 4, 2009, Pages 495-502

  Shima, Noriaki ^a   Katagi, Munehiro ^a   Tsuchihashi, Hitoshi ^a  

^a Chuo ward   (Japan)

Author keywords

3,4 methylenedioxymethamphetamine; Conjugate metabolite; Direct analysis; Liquid chromato graphy mass spectrometry; Methamphetamine

Indexed keywords

3,4 METHYLENEDIOXYMETHAMPHETAMINE; DESIGNER DRUG; METHAMPHETAMINE;

BLOOD SAMPLING; BODY FLUID; DRUG METABOLISM; ELECTROSPRAY MASS SPECTROMETRY; FORENSIC TOXICOLOGY; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; NONHUMAN; SAMPLING; SHORT SURVEY; URINALYSIS;

EID: 68949109862     PISSN: 13449702     EISSN: 13475207     Source Type: Journal    
DOI: 10.1248/jhs.55.495     Document Type: Short Survey

References (38)

1. National Police Agency of Japan Ed. (2006) White Paper on Police, National Police Agency, Tokyo, Japan.
2. Kulsudjarit, K. (2004) Drug problem in southeast and southwest Asia. Ann. N. Y. Acad. Sci., 1025, 446-457.
3. McKetin, R., Kozel, N., Douglas, J., Ali, R., Vicknasingam, B., Lund, J. and Li, J. H. (2008) The rise of methamphetamine in Southeast and East Asia. Drug Alcohol Rev., 27, 220-228.
4. Chung, H., Park, M., Hahn, E., Choi, H., Choi, H. and Lim,M. (2004) Recent trends of drug abuse and drug-associated deaths in Korea. Ann. N. Y. Acad. Sci., 1025, 458-464. (Pubitemid 39643894)
5. Fang, Y. X., Wang, Y. B., Shi, J., Liu, Z. M. and Lu, L. (2006) Recent trends in drug abuse in China. Acta Pharmacologica Sinica, 27, 140-144. (Pubitemid 43171150)
6. Katagi, M. and Tsuchihashi, H. (2002) Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 48, 14-21. (Pubitemid 41283462)
7. Uchiyama, N., Kikura-Hanajiri, R., Kawahara, N. and Goda, Y. (2008) Analysis of designer drugs detected in the products purchased in fiscal year 2006. Yakugaku Zasshi, 128, 1499-1505 (in Japanese).
8. Zaitsu, K., Katagi, M., Kamata, H. T., Miki, A. and Tsuchihashi, H. (2008) Discrimination and identification of regioisomeric β-keto analogues of 3,4-methylenedioxyamphetmaines by gas chromatography-mass spectrometry. Forensic Toxicology, 26, 45-51.
9. Becker, J., Neis, P., Rohrich, J. and Zorntlein, S. (2003) A fatal paramethoxymethamphetamine intoxication. Leg. Med. (Tokyo) Suppl., 1, 138-141.
10. Johansen, S. S., Hansen, A. C., Muller, I. B., Lundemose, J. B. and Franzmann, M. B. (2003) Three fatal cases of PMA and PMMA poisoning in Denmark. J. Anal. Toxicol., 27, 253-256.
11. Casale, J. F., Hays, P. A., Spratley, T. K. and Smith, P. R. (2006) The characterization of 4-methoxy-N-ethylamphetamine hydrochloride. Microgram Journals, 4, 42-46.
12. Bossong, M. G., Van Dijk, J. P. and Niesink, R. J. (2005) Methylone and mCPP, two new drugs of abuse? Addiction Biology, 10, 321-323.
13. Maurer, H. H., Kraemer, T., Springer, D. and Staack, R. F. (2004) Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamines (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis. Ther. Drug Monit., 26, 127-131. (Pubitemid 38501205)
14. Green, A. R., Mechan, A. O., Elliott, J. M., O'shea, E. and Colado, M. S. (2003) The pharmacology and clinical pharmacology of 3,4-(methylenedioxy) methamphetamine (MDMA, "Ecstasy"). Pharmacol. Rev., 55, 463-508.
15. Cozzi, N. V., Sievert, M. K., Shulgin, A. T., Jacob, III P. and Ruoho, A. E. (1999) Inhibition of plasma membrane monoamine transporters by β- ketoamphetamines. Eur. J. Pharmacol., 381, 63-69. (Pubitemid 29488590)
16. Dal Cason, T. A., Young, R. and Glennon, R. A. (1997) Cathinone: An investigation of several N-alkyl and methylenedioxy-substituted analogs. Pharmacol. Biochem. Behav., 58, 1109-1116. (Pubitemid 28108223)
17. Shulgin, A. (1991) PIHKAL: A Chemical Love Story, Transform Press, Berkeley, CA, U.S.A.
18. Shima, N., Katagi, M., Kamata, H., Zaitsu, K., Kamata, T., Miki, A., Tsuchihashi, H., Sakuma, T. and Nemoto, N. (2008) Conjugates of p-hydroxymethamphetamine and 4-hydroxy-3-methoxymethamphetamine in the blood obtained from methamphetamine and 3,4-methylenedioxymethamphetamine users: analysis by LC-MS-MS. Forensic Toxicology, 26, 58-65.
19. Miki, A., Katagi, M., Zaitsu, K., Nishioka, H. and Tsuchihashi, H. (2008) Development of a two-step injector for GC-MS with on-column derivatization, and its application to the determination of amphetamine-type stimulants (ATS) in biological specimens. J. Chromatogr. B Analyt. Tech. Biomed. Life Sci., 865, 25-32.
20. Kamata, H. T., Shima, N., Zaitsu, K., Kamata, T., Nishikawa, M., Katagi, M., Miki, A. and Tsuchihashi, H. (2007) Simultaneous analysis of new designer drug, methylone, and its metabolites in urine by gas chromatography-mass spectrometry and liquid chromatography-electrospray ionization mass spectrometry. Japanese Journal of forensic Science and Technology, 12, 97-106.
21. Miki, A., Katagi,M. and Tsuchihashi, H. (2003) Recent improvements in forensic hair analysis for illicit drugs. J. Health Sci., 49, 325-332. (Pubitemid 41289083)
22. Chèze, M., Deveaux, M., Martin, C., Lhermitte, M. and Pépin, G. (2007) Simultaneous analysis of six amphetamines and analogues in hair, blood and urine by LC-ESI-MS/MS. Application to the determination of MDMA after low ecstasy intake. Forensic Sci. Int., 170, 100-104.
23. Concheiro, M., Simões, S. M., Quintela, O., de Castro, A., Dias, M. J., Cruz, A. and López-Rivadulla, M. (2007) Fast LC-MS/MS method for the determination of amphetamine, methamphetamine, MDA, MDMA, MDEA, MBDB and PMA in urine. Forensic Sci. Int., 171, 44-51. (Pubitemid 47189627)
24. Klette, K. L., Jamerson, M. H., Morris-Kukoski, C. L., Kettle, A. R. and Suyder, J. J. (2005) Rapid simultaneous determination of amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine, 3,4- methylenedioxymethamphetamine, and 3,4-methylenedioxyethylamphetamine in urine by fast gas chromatography-mass spectrometry. J. Anal. Toxicol., 29, 669-674. (Pubitemid 41803355)
25. Kikura-Hanajiri, R., Kawamura, M., Saisho, K., Kodama, Y. and Goda, Y. (2007) The disposition into hair of new designer drugs; methylone, MBDB and methcathinone. J. Chromatogr. B Analyt. Tech. Biomed. Life Sci., 855, 121-126. (Pubitemid 47212020)
26. Shima, N., Kamata, H. T., Katagi, M. and Tsichihashi, H. (2006) Urinary excretion of the main metabolites of methamphetamine, including p-hydroxymethamphetamine-sulfate and phydroxymethamphetamine- glucuronide, in humans and rats. Xenobiotica, 36, 259-267.
27. Shima, N., Katagi, M., Kamata, H., Zaitsu, K., Kamata, T., Nishikawa, M., Miki, A., Tsichihashi, H., Sakuma, T. and Nemoto, N. (2008) Urinary excretion of the main metabolites of 3,4-methylenedioxymethamphetamine (MDMA), including the sulfate and glucuronide of 4-hydroxy-3-methoxymethamphetamine (HMMA), in humans and rats. Xenobiotica, 38, 314-324. (Pubitemid 351264448)
28. Kamata, H. T., Shima, N., Zaitsu, K., Kamata, T., Miki, A., Nishikawa, M., Katagi, M. and Tsuchihashi, H. (2006) Metabolism of the recently encountered designer drug, methylone, in humans and rats. Xenobiotica, 36, 709-723. (Pubitemid 44195985)
29. Zaitsu, K., Katagi, M., Kamata, T., Kamata, H., Shima, N., Tsuchihashi, H., Hayashi, T., Kuroki, H. and Matoba, R. (2008) Determination of a newly encountered designer drug "p-methoxyethylamphetamine" and its metabolites in human urine and blood. Forensic Sci. Int., 177, 77-84.
30. Zaitsu, K., Katagi, M., Kamata, H. T., Kamata, T., Shima, N., Miki, A., Tsuchihashi, H. and Mori, Y. (2009) Determination of the metabolites of new designer drugs bk-MBDB and bk-MDEA in human urine. Forensic Sci. Int., 188, 131-139.
31. Shima, N., Kamata, H. T., Kamata, T., Nishikawa, M., Katagi, M. and Tsuchihashi, H. (2007) The concentrations of glucuronide and sulfate of p-hydroxymethamphetamine in methamphetmaine users' urine, and optimization of their hydrolysis conditions. Japanese Journal of Forensic Science and Techology, 12, 73-82.
32. Pirnay, S. O., Abraham, T. T., Lowe, R. H. and Huestis, M. A. (2006) Selection and optimization of hydrolysis conditions for the quantification of urinary metabolites of MDMA. J. Anal. Toxicol., 30, 563-569.
33. Maurer, H. H., Bickeboeller-Friedrich, J., Kraemer, T. and Peters, F. T. (2000) Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ('Ecstasy'). Toxicol. Lett., 112-113, 133-142. (Pubitemid 30138114)
34. Shima, N., Tsutsumi, H., Kamata, T., Nishikawa, M., Katagi, M.,Miki, A. and Tsuchihashi, H. (2006) Direct determination of glucuronide and sulfate of p-hydroxymethamphetamine in methamphetamine users' urine. J. Chromatogr. B Analyt. Tech. Biomed. Life Sci., 830, 64-70. (Pubitemid 41831389)
35. Shima, N., Kamata, H. T., Katagi, M., Tsuchihashi, H., Sakuma, T. and Nemoto, N. (2007) Direct determination of glucuronide and sulfate of 4-hydroxy-3-methoxymethamphetamine, the main metabolite of MDMA, in human urine. J. Chromatogr. B Analyt. Tech. Biomed. Life Sci., 857, 123-129. (Pubitemid 47364837)
36. Shimosato, K., Tomita, M. and Ijiri, I. (1986) Urinary examination of p-hydroxylated methamphetamine metabolites in man. Arch. Toxicol., 59,135-140.
37. Hayakawa, K., Miyoshi, Y., Kurimoto, H., Matsushima, Y., Takayama, N., Tanaka, S. and Miyazaki, M. (1993) Simultaneous determination of methamphetamine and its metabolites in the urine samples of abusers by high performance liquid chromatography with chemiluminescence detection. Biol. Pharm. Bull., 16, 817-821. (Pubitemid 23329785)
38. th Annual Meeting of Japanese Association of Forensic Toxicology, 46-47.