Simultaneous liquid chromatographic-electrospray ionization mass spectrometric quantification of 3,4-methylenedioxymethamphetamine (MDMA, Ecstasy) and its metabolites 3,4-dihydroxymethamphetamine, 4-hydroxy-3-methoxymethamphetamine and 3,4-methylenedioxyamphetamine in squirrel monkey and human plasma after acidic conjugate cleavage

Forensic Science International

Volumn 184, Issue 1-3, 2009, Pages 64-68

  Mueller, Melanie ^a,b   Peters, Frank T ^a   Huestis, Marilyn A ^c   Ricaurte, George A ^b   Maurer, Hans H ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b JOHNS HOPKINS BAYVIEW MEDICAL CENTER   (United States)

^c NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

Author keywords

Acidic hydrolysis; Human plasma; LC ESI MS; MDMA; Metabolites; Validation

Indexed keywords

3,4 DIHYDROXYMETHAMPHETAMINE; 3,4 METHYLENEDIOXYAMPHETAMINE; 3,4 METHYLENEDIOXYMETHAMPHETAMINE; 4 HYDROXY 3 METHOXYMETHAMPHETAMINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; LIQUID CHROMATOGRAPHY; NEUROTOXICITY; NONHUMAN; NORMAL HUMAN; PRIORITY JOURNAL; SQUIRREL MONKEY; VALIDATION PROCESS;

EID: 58249136270     PISSN: 03790738     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.forsciint.2008.12.002     Document Type: Article

References (27)

1. Schwartz R.H., and Miller N.S. MDMA (ecstasy) and the rave: a review. Pediatrics 100 (1997) 705-708
2. Hegadoren K.M., Baker G.B., and Bourin M. 3,4-Methylenedioxy analogues of amphetamine: defining the risks to humans. Neurosci. Biobehav. Rev. 23 (1999) 539-553 (review)
3. Logan B.K. Amphetamines: an update on forensic issues. J. Anal. Toxicol. 25 (2001) 400-404
4. Jones A.L., and Simpson K.J. Review article: mechanisms and management of hepatotoxicity in ecstasy (MDMA) and amphetamine intoxications. Aliment. Pharmacol. Ther. 13 (1999) 129-133
5. Walubo A., and Seger D. Fatal multi-organ failure after suicidal overdose with MDMA, 'ecstasy': case report and review of the literature. Hum. Exp. Toxicol. 18 (1999) 119-125
6. Lora-Tamayo C., Tena T., and Rodriguez A. Amphetamine derivative related deaths. Forensic Sci. Int. 85 (1997) 149-157
7. Kalant H. The pharmacology and toxicology of "ecstasy" (MDMA) and related drugs. Can. Med. Assoc. J. 165 (2001) 917-928 (review)
8. Steele T.D., McCann U.D., and Ricaurte G.A. 3,4-Methylenedioxymethamphetamine (MDMA, "Ecstasy"): pharmacology and toxicology in animals and humans. Addiction 89 (1994) 539-551 (review)
9. McCann U.D., Ridenour A., Shaham Y., and Ricaurte G.A. Serotonin neurotoxicity after (+/-)3,4-methylenedioxymethamphetamine (MDMA; "Ecstasy"): a controlled study in humans. Neuropsychopharmacology 10 (1994) 129-138
10. Seiden L.S., and Sabol K.E. Methamphetamine and methylenedioxymethamphetamine neurotoxicity: possible mechanisms of cell destruction. NIDA Res. Monogr. 163 (1996) 251-276
11. Esteban B., O'Shea E., Camarero J., Sanchez V., Green A.R., and Colado M.I. 3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose. Psychopharmacology (Berl.) 154 (2001) 251-260
12. Gollamudi R., Ali S.F., Lipe G., Newport G., Webb P., Lopez M., Leakey J.E., Kolta M., and Slikker W. Influence of inducers and inhibitors on the metabolism in vitro and neurochemical effects in vivo of MDMA. Neurotoxicology 10 (1989) 455-466
13. Mueller M., Peters F.T., Ricaurte G.A., and Maurer H.H. Liquid chromatographic-electrospray ionization mass spectrometric assay for simultaneous determination of 3,4-methylenedioxymethamphetamine and its metabolites 3,4-methylenedioxyamphetamine 3,4-dihydroxymethamphetamine, and 4-hydroxy-3-methoxymethamphetamine in rat brain. J. Chromatogr. B 874 (2008) 119-124
14. Maurer H.H., Bickeboeller-Friedrich J., Kraemer T., and Peters F.T. Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ("Ecstasy"). Toxicol. Lett. 112 (2000) 133-142
15. Meyer M.R., Peters F.T., and Maurer H.H. The role of human hepatic cytochrome P450 isozymes in the metabolism of racemic MDMA and its enantiomers. Drug Metab. Dispos. 36 (2008) 2345-2354
16. Hiramatsu M., Kumagai Y., Unger S.E., and Cho A.K. Metabolism of methylenedioxymethamphetamine: formation of dihydroxymethamphetamine and a quinone identified as its glutathione adduct. J. Pharmacol. Exp. Ther. 254 (1990) 521-527
17. Miller R.T., Lau S.S., and Monks T.J. Metabolism of 5-(glutathion-S-yl)-alpha-methyldopamine following intracerebroventricular administration to male Sprague-Dawley rats. Chem. Res. Toxicol. 8 (1995) 634-641
18. Bai F., Lau S.S., and Monks T.J. Glutathione and N-acetylcysteine conjugates of alpha-methyldopamine produce serotonergic neurotoxicity: possible role in methylenedioxyamphetamine-mediated neurotoxicity. Chem. Res. Toxicol. 12 (1999) 1150-1157
19. de la Torre R., and Farre M. Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. Trends Pharmacol. Sci. 25 (2004) 505-508
20. Mueller M., Peters F.T., Ricaurte G.A., and Maurer H.H. Validated liquid chromatographic-electrospray ionization mass spectrometric assay for simultaneous determination of 3,4-methylenedioxymethamphetamine and its metabolites 3,4-methylenedioxyamphetamine 3,4-dihydroxymethamphetamine, and 4-hydroxy-3-methoxymethamphetamine in squirrel monkey plasma. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 855 (2007) 262-270
21. Kolbrich E.A., Lowe R.H., and Huestis M.A. Two-dimensional gas chromatography/electron-impact mass spectrometry with cryofocusing for simultaneous quantification of MDMA, MDA, HMMA, HMA, and MDEA in human plasma. Clin. Chem. 54 (2008) 379-387
22. Peters F.T. Method validation using LC-MS. In: Polettini A. (Ed). Applications of Liquid Chromatography-Mass Spectrometry in Toxicology (2006), Pharmaceutical Press, London p. 71
23. Peters F.T., Drummer O.H., and Musshoff F. Validation of new methods. Forensic Sci. Int. 165 (2007) 216-224
24. Dams R., Huestis M.A., Lambert W.E., and Murphy C.M. Matrix effect in bio-analysis of illicit drugs with LC-MS/MS: influence of ionization type, sample preparation, and biofluid. J. Am. Soc. Mass Spectrom. 14 (2003) 1290-1294
25. Maurer H.H. Position of chromatographic techniques in screening for detection of drugs or poisons in clinical and forensic toxicology and/or doping control. Clin. Chem. Lab. Med. 42 (2004) 1310-1324 (review)
26. Maurer H.H. Hyphenated mass spectrometric techniques-indispensable tools in clinical and forensic toxicology and in doping control. J. Mass Spectrom. 41 (2006) 1399-1413 (review)
27. Maurer H.H. Current role of liquid chromatography-mass spectrometry in clinical and forensic toxicology. Anal. Bioanal. Chem. 388 (2007) 1315-1325 (review)