Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 33, 2003 - Issue 10
67
Views
8
CrossRef citations to date
0
Altmetric
Research Article

Identification of some N-hydroxylated metabolites of (±)-3,4-methylenedioxymethamphetamine in horse urine by gas chromatography-mass spectrometry

Pages 1013-1025 | Received 11 Mar 2003, Published online: 22 Sep 2008

References

  • BECKETT, A. H., 1977, Metabolic oxidation of nitrogen and adjacent carbon atoms. In D. V. Parke and R. L. Smith (eds), Drug Metabolism — From Microbe to Man (London: Taylor & Francis), 33–42.
  • BECKETT, A. H. and AL-SARRAJ, S., 1972, N-Oxidation of primary and secondary amines to give hydroxylamines — a general metabolic route. Journal of Pharmacy and Pharmacology, 24, 916–917.
  • BECKETT, A. H. and BELANGER, P. M., 1974, Metabolism of chlorphentermine and phentermine in man to yield hydroxylamino, C-nitroso- and nitro-compounds. Journal of Pharmacy and Pharmacology, 26, 205–206.
  • BECKETT, A. H. and BELANGER, P. M., 1976, Metabolic N-Oxidation of secondary and primary aromatic amines as a route to ring hydroxylation, to various N-oxygenated products, and to dealkylation of secondary amines. Biochemical Pharmacology, 25, 211–214.
  • BECKETT, A. H., COUTTS, R. T. and OGUNBONA, F. A., 1974, The structure of nitrones derived from amphetamines. Journal of Pharmacy and Pharmacology, 26, 312–316.
  • BECKETT, A. H., NAVAS, G. E. and HUTT, A. J., 1988, Metabolism of chlorpromazine and promazine in vitro: isolation and characterization of N-oxidation products. Xenobiotica, 18, 61–74.
  • BECKETT, A. H., NAVAS, G. E., HUTT, A. J. and FARAG, M., 1979, Disappearing N-hydroxy compounds. Journal of Pharmacy and Pharmacology, 31, 476–477.
  • BOGEN, I. L., HAUG, K. H., MYHRE, 0. and FONNUM, F., 2003, Short- and long-term effects of MDMA ('ecstasy') on synaptosomal and vesicular uptake of neurotransmitters in vitro and ex vivo. Neurochemistry International, 43, 393–400.
  • CASHMAN, J. R., 2000, Human fiavin-containing monooxygenase: substrate specificity and role in drug metabolism. Current Drug Metabolism, 1, 181–191.
  • CASHMAN, J. R., XIONG, Y. N., Xu, L. and JANowsKY, A., 1999, N-Oxygenation of amphetamine and methamphetamine by the human fiavin-containing monooxygenase (form 3): role in bioactivation and detoxication. Journal of Pharmacology and Experimental Therapeutics, 288, 251–260.
  • CLAUWAERT, K. M., Van BOCXLAER, J. F., De LETTER, E. A., VAN CALENBERGH, S., LAMBERT, W. E. and DE LEENHEER, A. P., 2000, Determination of the designer drugs 3,4-methylenediox-ymethamphetamine, 3,4-methylenedioxyethylamphetamine, and 3,4-methylenedioxyampheta-mine with HPLC and fluorescence detection in whole blood, serum, vitreous humor, and urine. Clinical Chemistry, 46, 1968–1977.
  • CLEMENT, B., LUSTIG, K. L. and ZIEGLER, D. M., 1993, Oxidation of desmethylpromethazine catalyzed by pig liver fiavin-containing monooxygenase. Number and nature of metabolites. Drug Metabolism and Disposition, 21, 24–29.
  • COON, M. J., VAZ, A. D., MCGINNITY, D. F. and PENG, H. M., 1998, Multiple activated oxygen species in P450 catalysis: contributions to specificity in drug metabolism. Drug Metabolism and Disposition, 26, 1190–1193.
  • DE BOER, D., TAN, L. P., GORTER, P., VAN DE WAL, R. M. A., KETTENES-VAN DEN BOSCH, J. J., DE BRUIJN, E. A. and MAES, R. A. A., 1997, Gas chromatographic/mass spectrometric assay for profiling the enantiomers of 3,4-methylenedioxymethamphetamine and its chiral metabolites using positive chemical ionisation ion trap mass spectrometry. Journal of Mass Spectrometry, 32, 1236–1246.
  • DUMASIA, M. C., 1992, The biotransformation and detection of some 11-adrenergicmimetic drugs in the horse. In C. R. Short (ed.), Proceedings of the 9th International Conference of Racing Analysts and Veterinarians (Baton Rouge: Department of Veterinary Physiology, Louisiana State University), vol. II, 75–90.
  • DUMASIA, M. C., 2001, Drug metabolism in the horse: some interesting pathways. In R. B. Williams, E. Houghton and J. F. Wade (eds), Proceedings of the 13th International Conference of Racing Analysts and Veterinarians (Newmarket: R. & W.), 155-161.
  • DUMASIA, M. C. and HOUGHTON, E., 1991, Screening and confirmatory analysis of beta-agonists, beta-antagonists and their metabolites in horse urine by capillary gas chromatography-mass spectrometry. Journal of Chromatography B Biomedical Applications, 564, 503–513.
  • GIMENO, P., BESACIER, F., CHAUDRON-THOZET, H., GIRARD, J. and LAMOTTE, A., 2002, A contribution to the chemical profiling of 3,4-methylenedioxymethamphetamine (MDMA) tablets. Forensic Science International, 127, 1–44.
  • HELMLIN, H. J., BRACHER, K., BOURQUIN, D., VONLANTHEN, D. and BRENNEISEN, R., 1996, Analysis of 3,4-methylenedioxymethamphetamine (MDMA) and its metabolites in plasma and urine by HPLC-DAD and GC-MS. Journal of Analytical Toxicology, 20, 432–440.
  • HIRAMATSU, M., KUMAGAI. Y., UNGER, S. E. and CHO, A. K., 1990, Metabolism of methylenedioxymethamphetamine: formation of dihydroxymethamphetamine and a quinone identified as its glutathione adduct. Journal of Pharmacology and Experimental Therapeutics, 254, 521–527.
  • HLAVICA, P., 2002, N-Oxidative transformation of free and N-substituted amine functions by cytochrome P450 as means of bioactivation and detoxication. Drug Metabolism Reviews, 34, 451–477.
  • JURADO, C., GIMENEZ, M. P., SORIANO, T., MENENDEZ, M. and REPETTO, M., 2000, Rapid analysis of amphetamine, methamphetamine, MDA, and MDMA in urine using solid-phase microextrac-tion, direct on-fibre derivatization, and analysis by GC-MS. Journal of Analytical Toxicology, 24, 11–16.
  • KINTZ, P. and SAMY N., 1999, Determination of 'Ecstasy' components in alternative biological specimens. Journal of Chromatography B Biomedical Science Applications, 733, 137–143.
  • KRETH, K., KOVAR, K., SCHWAB, M. and ZANGER, U. M., 2000, Identification of the human cytochromes P450 involved in the oxidative metabolism of 'Ecstasy'-related designer drugs. Biochemical Pharmacology, 59, 1563–1571.
  • KUMAGAI, Y., LIN, L. Y., HIRATSUKA, A., NARIMATSU, S., SUZUKI, T., YAMADA, H., OGURI, K., YOSHIMURA, H. and CHO, A. K., 1994, Participation of cytochrome P450-2B and -2D isozymes in the demethylenation of methylenedioxymethamphetamine enantiomers by rats. Molecular Pharmacology, 45, 359–365.
  • LIM, H. K. and FOLTZ, R. L., 1988, In vivo and in vitro metabolism of 3,4-(methylenedioxy)-methamphetamine in the rat: identification of metabolites using an ion trap detector. Chemical Research in Toxicology, 1, 370–378.
  • LIM, H. K. and FOLTZ, R. L., 1991, In vivo formation of aromatic hydroxylated metabolites of 3,4-(methylenedioxy)methamphetamine in the rat: identification by ion trap tandem mass spectrometric (MS/MS and MS/MS/MS) techniques. Biological Mass Spectrometry, 20, 677–686.
  • LINDEKE, B., CH0, A. K., JoNssoN, U. and PAULSEN, U., 1978, On the chemical stability of beta-hydroxyphenylalkylhydroxylamines and its relevance to the metabolism of amphetamines and ephedrines. Life Sciences, 23, 921–926.
  • LINDEKE, B., CHO, A. K., THOMAS, T. L. and MICHELSON, L., 1973, Microsomal N-hydroxylation of phenylalkylamines. Identification of N-hydroxylated phenylalkylamines as their trimethylsilyl derivatives by GC-MS. Acta Pharmaceutica Suecica, 10, 493–506.
  • MAURER, H. H., 1996, On the metabolism and the toxicological analysis of methylenedioxyphenylalk-ylamine designer drugs by gas chromatography-mass spectrometry. Therapeutic Drug Monitoring, 18, 465–470.
  • MAURER, H. H., BICKEBOELLER-FRIEDRICH, J., KRAEMER, T. and PETERS, F. T. 2000, Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs (`Ecstasy'). Toxicology Letters, 112–113, 133–142.
  • MCCOOEYE, M. A., MESTER, Z., ELLS, B., BARNETT, D. A., PURVES, R. W. and GUEVREMONT, R., 2002, Quantitation of amphetamine, methamphetamine, and their methylenedioxy derivatives in urine by solid-phase microextraction coupled with electrospray ionisation-high-field asymmetric waveform ion mobility spectrometry-mass spectrometry. Analytical Chemistry, 74, 3071–3075.
  • MORTIER, K. A., DAMS, R., LAMBERT, W. E., De LETTER, E. A., Van CALENBERGH, S. and DE LEENHEER, A. P. 2002, Determination of paramethoxyamphetamine and other amphetamine-related designer drugs by liquid chromatography/sonic spray ionization mass spectrometry. Rapid Communications in Mass Spectrometry, 16, 865–870.
  • NAVARRO, M., PICHINI, S., FARRE, M., ORTUNO, J., ROSET, P. N., SEGURA, J. and DE LA TORRE, R., 2001, Usefulness of saliva for measurement of 3,4-methylenedioxymethamphetamine and its metabolites: correlation with plasma drug concentrations and effect of salivary pH. Clinical Chemistry, 47, 1788–1795.
  • ORTUNO, J., PIZARRO, N., FARRE, M., MAS, M., SEGURA, J., CAMI, J., BRENNEISEN, R. and DE LA TORRE, R., 1999, Quantification of 3,4-methylenedioxymetamphetamine and its metabolites in plasma and urine by gas chromatography with nitrogen-phosphorus detection. Journal of Chromatography B Biomedical Science Applications, 723, 221–232.
  • PALHOL, F., BOYER, S., NAULET, N. and CHABRILLAT, M., 2002, Impurity profiling of seized MDMA tablets by capillary gas chromatography. Analytical and Bioanalytical Chemistry, 374, 274-281. PARROTT, A. C., 2002, Recreational Ecstasy/MDMA, the serotonin syndrome, and serotonergic neurotoxicity. Pharmacology Biochemistry and Behaviour, 71, 837–844.
  • PENTNEY, A. R., 2001, An exploration of the history and controversies surrounding MAMA and MDA. Journal of Psychoactive Drugs, 33, 213–221.
  • PIZARRO, N., LLEBARIA, A., CANO, S., JOGLAR, J., FARRE, M., SEGURA, J. and DE LA TORRE, R., 2003, Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry. Rapid Communications in Mass Spectrometry, 17, 330–336.
  • PIZARRO, N., ORTUNO, J., FARRE, M., HERNANDEZ-LOPEZ, C., PUJADAS, M., LLEBARIA, A., JOGLAR, J., ROSET, P. N., MAS, M., SEGURA, J., CAMI, J. and DE LA TORRE, R., 2002, Determination of MDMA and its metabolites in blood and urine by gas chromatography-mass spectrometry and analysis of enantiomers by capillary electrophoresis. Journal of Analytical Toxicology, 26, 157–165.
  • POKLIS, A., FITZGERALD, R. L., HALL, K. V. and SAADY, J. J., 1993, EMIT-d.a.u. monoclonal amphetamine/methamphetamine assay. II. Detection of methylenedioxyamphetamine (MDA) and methylenedioxymethamphetamine (MDMA). Forensic Science International, 59, 63–70.
  • RAMSEIER, A., SIETHOFF, C., CASLAVSKA, J. and THORMANN, W., 2000, Confirmation testing of amphetamines and designer drugs in human urine by capillary electrophoresis-ion trap mass spectrometry. Electrophoresis, 21, 380–387.
  • SEGURA, M., ORTUNO, J., FARRE, M., MCLURE, J. A., PUJADAS, M., PIZARRO, N., LLEBARIA, A., JOGLAR, J., ROSET, P. N., SEGURA, J. and DE LA TORRE, R., 2001, 3,4-Dihydroxymethamphe-tamine (HHMA). A major in vivo 3,4-methylenedioxymethamphetamine (MDMA) metabolite in humans. Chemical Research in Toxicology, 14, 1203–1208.
  • SEGURA, M., ORTUNO, J., MCLURE, J. A., PUJADAS, M., PIZARRO, N., FARRE, M., LLEBARIA, A., JOGLAR, J., SEGURA, J. and DE LA TORRE, R., 2002, High-performance liquid chromatography with electrochemical detection applied to the analysis of 3,4-dihydroxymethamphetamine in human plasma and urine. Journal of Chromatography B Analytical Technologies in the Biomedical Life Sciences, 769, 313–321.
  • TAGLIARO, F., DE BATTISTI, Z., GROPPI, A., NAKAHARA, Y., SCARCELLA, D., VALENTINI, R. and MARIGO, M., 1999, High sensitivity simultaneous determination in hair of the major constituents of ecstasy (3,4-methylenedioxymethamphetamine, 3,4-methylenedioxyamphetamine and 3,4-methylenedioxyethylamphetamine) by high-performance liquid chromatography with direct fluorescence detection. Journal of Chromatography B Biomedical Science Applications, 723, 195–202.
  • TUCKER, G. T., LENNARD, M. S., ELLIS, S. W., WOODS, H. F., CHO, A. K., LIN, L. Y., HIRATSUKA, A., SCHMITZ, D. A. and CHu, T. Y., 1994, The demethylenation of methylenedioxymethamphe-tamine ('ecstasy') by debrisoquine hydroxylase (CYP2D6). Biochemical Pharmacology, 47, 1151–1156.
  • VALAER, A. K., RAVIS, W. R. and CLARK, C. R., 1990, Liquid chromatographic properties and aqueous solution stability of N-hydroxy-3,4-methylenedioxyamphetamine. Journal of Chromatographic Science, 28, 482–486.
  • YOUSIF, M. Y., FITZGERALD, R. L., NARASIMHACHARI, N., ROSECRANS, J. A., BLANKE, R. V. and GLENNON, R. A., 1990, Identification of metabolites of 3,4-methylenedioxy methamphetamine in rats. Drug and Alcohol Dependence, 26, 127–135.
  • ZIEGLER, D. M., 2002, An overview of the mechanism, substrate specificities, and structure of FM0s. Drug Metabolism Reviews, 34, 503–511.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.