Conjugates of p-hydroxymethamphetamine and 4-hydroxy-3- methoxymethamphetamine in blood obtained from methamphetamine and 3,4-methylenedioxymethamphetamine users: Analysis by LC-MS-MS

Forensic Toxicology

Volumn 26, Issue 2, 2008, Pages 58-65

  Shima, Noriaki ^a   Katagi, Munehiro ^a   Kamata, Hiroe ^a   Zaitsu, Kei ^a   Kamata, Tooru ^a   Miki, Akihiro ^a   Tsuchihashi, Hitoshi ^a   Sakuma, Tsutomu ^b   Nemoto, Nobuo ^b  

^a Chuo ward   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Blood; Glucuronide conjugate; LC MS MS; MDMA; Methamphetamine; Sulfate conjugate

Indexed keywords

3,4 METHYLENEDIOXYMETHAMPHETAMINE; 4 HYDROXY 3 METHOXYMETHAMPHETAMINE; GLUCURONIDE; METHAMPHETAMINE; PHOLEDRINE; SULFATE; UNCLASSIFIED DRUG;

ADULT; ANALYTIC METHOD; ARTICLE; BLOOD ANALYSIS; BLOOD LEVEL; CONJUGATE; CONJUGATION; ELECTROSPRAY MASS SPECTROMETRY; FEMALE; HUMAN; HUMAN TISSUE; LIQUID CHROMATOGRAPHY; MALE; PRIORITY JOURNAL;

EID: 57049127605     PISSN: 18608965     EISSN: 18608973     Source Type: Journal    
DOI: 10.1007/s11419-008-0054-x     Document Type: Article

References (28)

1. National Police Agency of Japan (2006) White paper on police 2005. Tokyo, Japan
2. V.A. Skrinska S.B. Gock 2005 Measurement of 3,4-MDMA and related amines in diagnostic and forensic laboratories Clin Lab Sci 18 119 123
3. C. Jurado M.P. Gimenez T. Soriano M. Menendez M. Repetto 2000 Rapid analysis of amphetamine, methamphetamine, MDA, and MDMA in urine using solid-phase microextraction, direct on-fiber derivatization, and analysis by GC-MS J Anal Toxicol 24 11 16
4. P. Stout C. Horn L. Klette 2002 Rapid simultaneous determination of amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymethamphetamine, and 3,4-methylenedioxyethylamphetamine in urine by solid-phase extraction and GC-MS: a method optimized for high-volume laboratories J Anal Toxicol 26 253 261
5. J. Furesz G. Kocsis A. Gachalyi G. Karvaly O. Boldis 2004 Mass selective detection of amphetamine, methamphetamine, and related compounds in urine J Chromatogr Sci 42 259 262
6. M. Nishida A. Namera M. Yashiki K. Kimura 2004 Miniaturized sample preparation method for determination of amphetamines in urine Forensic Sci Int 143 163 167
7. K.L. Klette M.H. Jamerson C.L. Morris-Kukoski A.R. Kettle J.J. Suyder 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
8. 14C]methamphetamine in man, the guinea pig and the rat Biochem J 129 11 22
9. K. Shimosato M. Tomita I. Ijiri 1986 Urinary examination of p-hydroxylated methamphetamine metabolites in man Arch Toxicol 59 135 140
10. K. Hayakawa Y. Miyoshi H. Kurimoto Y. Matsushima N. Takayama S. Tanaka M. Miyazaki 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
11. N. Shima H.T. Kamata M. Katagi H. Tsichihashi 2006 Urinary excretion of the main metabolites of methamphetamine, including p-hydroxymethamphetamine- sulfate and phydroxymethamphetamine-glucuronide, in humans and rats Xenobiotica 36 259 267
12. M. Delaforge M. Jaouen G. Bouille 1999 Inhibitory metabolite complex formation of methylenedioxymethamphetamine with rat and human cytochrome P450. Particular involvement of CYP2D Environ Toxicol Pharmacol 7 153 158
13. M. Segura J. Ortuño M. Farré J.A. McLure M. Pujadas N. Pizarro A. Llebaria J. Joglar P.N. Roset J. Segura R. de la Torre 2001 3,4-Dihydroxymethamphetamine (HHMA). A major in vivo 3,4- methylenedioxymethamphetamine (MDMA) metabolite in humans Chem Res Toxicol 14 1203 1208
14. R. de la Torre M. Farre P.N. Roset N. Pizarro S. Abanades M. Segura J. Segura J. Cami 2004 Human pharmacology of MDMA: pharmacokinetics, metabolism and disposition Ther Drug Monit 26 137 144
15. H.K. Lim R.L. Foltz 1989 Identification of metabolites of 3,4-(methylenedioxy)methamphetamine in human urine Chem Res Toxicol 2 142 143
16. H.K. Lim S. Zeng D.M. Chei R.L. Foltz 1992 Comparative investigation of disposition of 3,4-(methylenedioxy)metham phetamine (MDMA) in the rat and the mouse by a capillary gas chromatography-mass spectrometry assay based on perfluorotributylamine-enhanced ammonia positive ion chemical ionization J Pharm Biomed Anal 10 657 665
17. H.J. Helmlin K. Bracher D. Bourquin D. Vonlanthen R. Brenneisen 1996 Analysis of 3,4-methylenedioxymethamphetamine (MDMA) and its metabolites in plasma and urine by HPLC-DAD and GC-MS J Anal Toxicol 20 432 440
18. H.H. Maurer J. Bickeboeller-Friedrich T. Kraemer F.T. Peters 2000 Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ('Ecstasy') Toxicol Lett 112-113 133 142
19. S.O. Pirnay T.T. Abraham R.H. Lowe M.A. Huestis 2006 Selection and optimization of hydrolysis conditions for the quantification of urinary metabolites of MDMA J Anal Toxicol 30 563 569
20. N. Shima M. Katagi H. Kamata K. Zaitsu T. Kamata M. Nishikawa A. Miki H. Tsuchihashi T. Sakuma N. Nemoto 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
21. A. Ogamo M. Ueda M. Fukumoto 2001 N-Demethylation of methamphetamine and selegiline Jpn J Forensic Toxicol 19 140 141
22. Shulgin A, Shulgin A (1997) TiHKAL: the communication. Transform, Berkeley, pp 714-719
23. Shulgin A, Shulgin A (1997) TiHKAL: the communication. Transform, Berkeley, pp 733-739
24. Buzas A, Dufour C (1950) Sur la preparation de la β-(paraoxyphenyl)- isopropyl-methyl-amine. Bull Soc Chim Fr 139-140
25. H.K. Lim R.L. Foltz 1988 In vivo and in vitro metabolism of 3,4-(methylenedioxy)methamphetamine in the rat: identification of metabolites using an ion trap detector Chem Res Toxicol 1 370 378
26. N. Shima H. Tsutsumi T. Kamata M. Nishikawa M. Katagi A. Miki H. Tsuchihashi 2006 Direct determination of glucuronide and sulfate of p-hydroxymethamphetamine in methamphetamine users' urine J Chromatogr B 830 64 70
27. N. Shima H.T. Kamata M. Katagi H. Tsuchihashi T. Sakuma N. Nemoto 2007 Direct determination of glucuronide and sulfate of 4-hydroxy-3- methoxymethamphetamine, the main metabolite of MDMA, in human urine J Chromatogr B 857 123 129
28. N. Shima H.T. Kamata T. Kamata M. Nishikawa M. Katagi H. Tsuchihashi 2007 The concentrations of glucuronide and sulfate of p-hydroxymethamphetamine in methamphetamine users' urine, and optimization of their hydrolysis conditions Jpn J Forensic Sci Tech 12 73 82