In vivo metabolism of the new designer drug 1-(4-methoxyphenyl)piperazine (MeOPP) in rat and identification of the human cytochrome P450 enzymes responsible for the major metabolic step

Reference

• BACH, M. V., COUTTS, R. T. and BAKER, G. B., 1999, Involvement of CYP2D6 in the in vitro metabolism of amphetamine, two N-alkylamphetamines and their 4-methoxylated derivatives. Xenobiotica, 29, 719–732.
   PubMed Web of Science ®Google Scholar
• BALMELLI, C., KUPFERSCHMIDT, H., RENTSCH, K. and SCHNEEMANN, M., 2001, [Fatal brain edema after ingestion of ecstasy and benzylpiperazine]. Deutsche Medizinische Wochenschrift, 126, 809–811.
   PubMed Web of Science ®Google Scholar
• BERTILSSON, L., 1995, Geographical/interracial differences in polymorphic drug oxidation. Current state of knowledge of cytochromes P450 (CYP) 2D6 and 2C19. Clinical Pharmacokinetics, 29, 192–209.
   PubMed Web of Science ®Google Scholar
• BOURRIE, M., MEUNIER, V., BERGER, Y. and FABRE, G., 1996, Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalysed by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 277, 321–332.
   PubMed Web of Science ®Google Scholar
• CACCIA, S., FONG, M. H. and URSO, R., 1985, Ionization constants and partition coefficients of 1-arylpiperazine derivatives. Journal of Pharmaceutics and Pharmacology, 37, 567–570.
   PubMed Web of Science ®Google Scholar
• CLARKE, S. E., 1998, In vitro assessment of human cytochrome P450. Xenobiotica, 28, 1167–1202.
   PubMed Web of Science ®Google Scholar
• DE BOER, D., BOSMAN, I. J., HIDVEGI, E., MANZONI, C., BENKO, A. A., Dos, R. L. and MAES, R. A., 2001, Piperazine-like compounds: a new group of designer drugs-of-abuse on the European market. Forensic Science International, 121, 47–56.
   PubMedGoogle Scholar
• DRUG ENFORCEMENT ADMINISTRATION — DEPARTMENT OF JUSTICE, 2002, Schedules of controlled substances: temporary placement of benzylpiperazine and trifiuoromethylphenylpiperazine into schedule I. Federal Register, 67, 59161–59162.
   Google Scholar
• DRUG ENFORCEMENT ADMINISTRATION — OFFICE OF FORENSIC SCIENCES, 2002, Unusual piperazine mixture in Alliance, Ohio. Microgram, 35, 190.
   Google Scholar
• DRUG ENFORCEMENT ADMINISTRATION — OFFICE OF FORENSIC SCIENCES, 2003, Piperazine mixture tablets in Chicago, Illinois. Microgram, 36, 6–7.
   Google Scholar
• EVANS, W. E. and MuLE0D, H. L., 2003, Pharmacogenomics — drug disposition, drug targets, and side effects. New England Journal of Medicine, 348, 538–549.
   Google Scholar
• GLENNON, R. A., 1987, Central serotonin receptors as targets for drug research. Journal of Medical Chemistry, 30, 1–12.
   PubMedGoogle Scholar
• HOWARD, L. A., SELLERS, E. M. and TYNDALE, R. F., 2002, The role of pharmacogenetically-variable cytochrome P450 enzymes in drug abuse and dependence. Pharmacogenomics, 3, 185–199.
   PubMed Web of Science ®Google Scholar
• IOANNIDES, C., 2001, Enzyme Systems that Metabolise Drugs and Other Xenobiotics (New York: Wiley). KANAMORI, T., INouE, H., IWATA, Y., OHMAE, Y. and KISHI, T., 2002, In vivo metabolism of 4-bromo- 2,5-dimethoxyphenethylamine (2C-B) in the rat: identification of urinary metabolites. Journal of Analytical Toxicology, 26, 61–66.
   Google Scholar
• KOBAYASHI, S., MURRAY, S., WATSON, D., SESARDIC, D., DAVIES, D. S. and BOOBIS, A. R., 1989, The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine in the rat is the inverse of that in man. Biochemical Pharmacology, 38, 2795–2799.
   PubMed Web of Science ®Google Scholar
• KRAEMER, T., BICKEBOELLER-FRIEDRICH, J. and MAURER, H. H., 2000, On the metabolism of the amphetamine-derived antispasmodic drug mebeverine: gas chromatography-mass spectrometry studies on rat liver microsomes and on human urine. Drug Metabolism and Disposition, 28, 339–347.
   PubMedGoogle Scholar
• LYON, R. A., TITELER, M., MCKENNEY, J. D., MAGEE, P. S. and GLENNON, R. A., 1986, Synthesis and evaluation of phenyl- and benzoylpiperazines as potential serotonergic agents. Journal of Medical Chemistry, 29, 630–634.
   PubMed Web of Science ®Google Scholar
• MARGOLIS, J. M. and OBACH, R. S., 2003, Impact of nonspecific binding to microsomes and phospholipid on the inhibition of cytochrome P4502D6: implications for relating in vitro inhibition data to in vivo drug interactions. Drug Metabolism and Disposition, 31, 606–611.
   PubMed Web of Science ®Google Scholar
• MAURER, H. H., 2000a, Methods for GC-MS. In K. Pfieger, H. H. Maurer and A. Weber (eds), Mass Spectral and GC Data of Drugs, Poisons, Pesticides, Pollutants and their Metabolites, Part 4 (Weinheim: Wiley-VCH), pp. 3–241.
   Google Scholar
• MAURER, H. H., 2000b, Screening procedures for simultaneous detection of several drug classes used in the high throughput toxicological analysis and doping control [review]. Combined Chemical High Throughput Screening, 3, 461–474.
   Google Scholar
• MAURER, H. H. and BICKEBOELLER-FRIEDRICH, J., 2000, Screening procedure for detection of antidepressants of the selective serotonin reuptake inhibitor type and their metabolites in urine as part of a modified systematic toxicological analysis procedure using gas chromatography-mass spectrometry. Journal of Analytical Toxicology, 24, 340–347.
   Google Scholar
• MAURER, H. H., KRATZSCH, C., WEBER, A. A., PETERS, F. T. and KRAEMER, T., 2002, Validated assay for quantification of oxcarbazepine and its active dihydro metabolite 10-hydroxy carbazepine in plasma by atmospheric pressure chemical ionization liquid chromatography/mass spectrometry. Journal of Mass Spectrometry, 37, 687–692.
   PubMed Web of Science ®Google Scholar
• McKAY, A. F., OTT, W. L., TAYLOR, G. W., BUCHANAN, M. N. and CROOKER, J. F., 1950, Diazohydrocarbons. Canadian Journal of Research, 28, 683–688.
   Google Scholar
• MCLAFFERTY, F. W. and TURECEK, F., 1993, Interpretation of Mass Spectra (Mill Valley: University Science Books).
   Google Scholar
• MURPHY, D. L., LESCH, K. P., AULAKH, C. S. and PIGOTT, T. A., 1991, Serotonin-selective arylpiperazines with neuroendocrine, behavioral, temperature, and cardiovascular effects in humans. Pharmacology Review, 43, 527–552.
   PubMed Web of Science ®Google Scholar
• NEWTON, D. J., WANG, R. W. and Lu, A. Y., 1995, Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metabolism and Disposition, 23, 154–158.
   PubMed Web of Science ®Google Scholar
• PAUL, L. D. and MAURER, H. H., 2003, Studies on the metabolism and toxicological detection of the Eschscholtzia californica alkaloids californine and protopine in urine using gas chromatography-mass spectrometry. Journal of Chromatography B, 789, 43–57.
   PubMed Web of Science ®Google Scholar
• PAWLOWSKI, L., 1983, A serotonergic component in the central action of 1-(o-methoxypheny1)-piperazine. Polish Journal of Pharmacology and Pharmaceutics, 35, 319–326.
   PubMedGoogle Scholar
• ROESNER, P., JUNGE, T., FRITSCHI, G., KLEIN, B., THIELERT, K. and KOZLOWSKI, M., 1999, Neue synthetische Drogen: Piperazin-, Procyclidin- und alpha-Aminopropiophenonderivate. Toxichem. Krimtech., 66, 81–90.
   Google Scholar
• SHULGIN, A., 1991, #142 PEA; Phenethylamine. In D. Joy (ed.), Pihkal, A Chemical Love Story (Berkley: Transform), pp. 815-818.
   Google Scholar
• SMITH, D. A., ABEL, S. M., HYLAND, R. and JoNEs, B. C., 1998, Human cytochrome P450s: selectivity and measurement in vivo. Xenobiotica, 28, 1095–1128.
   PubMed Web of Science ®Google Scholar
• SMITH, R. M. and BUSCH, K. L., 1999, Understanding Mass Spectra — A Basic Approach (New York: Wiley).
   Google Scholar
• SPRINGER, D., FRITSCHI, G. and MAURER, H. H., 2003a, Metabolism and toxicological detection of the new designer drug 3',4'-methylenedioxy-alpha-pyrrolidinopropiophenone studied in urine using gas chromatography-mass spectrometry. Journal of Chromatography B, 793, 377–388.
   PubMed Web of Science ®Google Scholar
• SPRINGER, D., FRITSCHI, G. and MAURER, H. H., 2003b, Metabolism and toxicological detection of the new designer drug 4'-methoxy-alpha-pyrrolidinopropiophenone studied in urine using gas chromatography-mass spectrometry. Journal of Chromatography B, 793, 331–342.
   PubMed Web of Science ®Google Scholar
• SPRINGER, D., PAUL, L. D., STAACK, R. F., KRAEMER, T. and MAURER, H. H., 2003c, Identification of the cytochrome P450 enzymes involved in the metabolism of 4'-methyl-(alpha)-pyrrolidinopropiophenone, a novel scheduled designer drug, in human liver microsomes. Drug Metabolism and Disposition, 31, 979–982.
   PubMed Web of Science ®Google Scholar
• SPRINGER, D., PETERS, F. T., FRITSCHI, G. and MAURER, H. H., 2002, Studies on the metabolism and toxicological detection of the new designer drug 4'-methyl-alpha-pyrrolidinopropiophenone in urine using gas chromatography-mass spectrometry. Journal of Chromatography B, 773, 25–33.
   PubMed Web of Science ®Google Scholar
• SPRINGER, D., PETERS, F. T., FRITSCHI, G. and MAURER, H. H., 2003d, New designer drug 4'-methyl-alpha-pyrrolidinohexanophenone: studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry. Journal of Chromatography B, 789, 79–91.
   PubMed Web of Science ®Google Scholar
• SPRINGER, D., STAACK, R. F., PAUL, L. D., KRAEMER, T. and MAURER, H. H., 2003e, Identification of cytochrome P450 enzymes involved in the metabolism of 4'-methoxy-pyrrolidinopropiophenone (MOPPP), a designer drug, in human liver microsomes. Xenobiotica, 33, 989–998.
   PubMed Web of Science ®Google Scholar
• STAACK, R. F., FEHN, J. and MAURER, H. H., 2003a, New designer drug para-methoxymethamphe-tamine: studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry. Journal of Chromatography B, 789, 27–41.
   PubMedGoogle Scholar
• STAACK, R. F., FRITSCHI, G. and MAURER, H. H., 2002, Studies on the metabolism and the toxicological analysis of the new piperazine-like designer drug N-benzylpiperazine in urine using gas chromatography-mass spectrometry. Journal of Chromatography B, 773, 35–46.
   PubMed Web of Science ®Google Scholar
• STAACK, R. F., FRITSCHI, G. and MAURER, H. H., 2003b, New designer drug 1-(3-trifluoromethylphenyBpiperazine (TFMPP): GC/MS and LC/MS studies on its phase I and II metabolism and on its toxicological detection in urine. Journal of Mass Spectrometry, 38, 971–981.
   PubMed Web of Science ®Google Scholar
• STAACK, R. F. and MAURER, H. H., 2003a, Piperazine-derived designer drug 1-(3-chlorophenyl)piper-azine (mCPP): GC-MS studies on its metabolism and its toxicological detection in urine including analytical differentiation from its precursor drugs trazodone and nefazodone. Journal of Analytical Toxicology, 27, 560–568.
   PubMed Web of Science ®Google Scholar
• STAACK, R. F. and MAURER, H. H., 2003b, Toxicological detection of the new designer drug 1-(4-methoxyphenyl)piperazine and its metabolites and differentiation from an intake of structurally related medicaments in urine using gas chromatography-mass spectrometry. Journal of Chromatography B, Analytical Technologies in the Biomedical and Life Sciences, 798, 333–342.
   PubMedGoogle Scholar
• TRACHSEL, D. and RICHARD, N., 2000, Psychedelische Chemie (Solothurn: Nachtschatten).
   Google Scholar
• WAX, P. M., 2002, Just a click away: recreational drug Web sites on the Internet. Pediatrics, 109, e96. Wu, D., OTTON, S. V., INABA, T., KALOW, W. and SELLERS, E. M., 1997, Interactions of amphetamine analogs with human liver CYP2D6. Biochemical Pharmacology, 53, 1605–1612.
   Google Scholar
• Yu, A. M., IDLE, J. R., BYRD, L. G., KRAUSZ, K. W., KUPFER, A. and GONZALEZ, F. J., 2003a, Regeneration of serotonin from 5-methoxytryptamine by polymorphic human CYP2D6. Pharmacogenetics, 13, 173–181.
   PubMedGoogle Scholar
• Yu, A. M., IDLE, J. R., KRAUSZ, K. W., KUPFER, A. and GONZALEZ, F. J., 2003b, Contribution of individual cytochrome P450 isozymes to the 0-demethylation of the psychotropic beta-carboline alkaloids harmaline and harmine. Journal of Pharmacology and Experimental Therapeutics, 305, 315–322.
   PubMed Web of Science ®Google Scholar