New cathinone-derived designer drugs 3-bromomethcathinone and 3-fluoromethcathinone: Studies on their metabolism in rat urine and human liver microsomes using GC-MS and LC-high-resolution MS and their detectability in urine

Journal of Mass Spectrometry

Volumn 47, Issue 2, 2012, Pages 253-262

  Meyer, Markus R ^a   Vollmar, Christian ^a   Schwaninger, Andrea E ^a   Wolf, Ehud Udi ^b   Maurer, Hans H ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b Israel Police   (Israel)

Author keywords

3 BMC; 3 FMC; CYP; designer drugs; GC MS; HR MS; metabolism; STA

Indexed keywords

3-BMC; 3-FMC; CYP; DESIGNER DRUGS; GC-MS; HR-MS; STA;

BIOMOLECULES; BODY FLUIDS; CHEMICAL REACTIONS; DESIGN; DRUG INTERACTIONS; ENZYMES; METABOLITES; PHYSIOLOGY; RATS;

METABOLISM;

3 BROMOMETHCATHINONE; 3 FLUOROMETHCATHINONE; CATHINONE; CYTOCHROME P450 2B6; CYTOCHROME P450 ISOENZYME; DESIGNER DRUG; ILLICIT DRUG; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; ENZYME KINETICS; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MASS FRAGMENTOGRAPHY; NONHUMAN; PRIORITY JOURNAL; RAT; TOXICOLOGY; URINALYSIS;

ALKALOIDS; ANIMALS; ARYL HYDROCARBON HYDROXYLASES; CHROMATOGRAPHY, LIQUID; CYTOCHROME P-450 CYP2D6; DESIGNER DRUGS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; KINETICS; MALE; MICROSOMES, LIVER; OXIDOREDUCTASES, N-DEMETHYLATING; PROPIOPHENONES; RATS;

RATTUS;

EID: 84857462045     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.2960     Document Type: Article

References (26)

1. E. E. Balint, G. Falkay, G. A. Balint,. Khat-a controversial plant. Wien. Klin. Wochenschr. 2009, 121, 604.
2. K. F. Foley, N. V. Cozzi,. Inhibition of transport function and desipramine binding at the human noradrenaline transporter by N-ethylmaleimide and protection by substrate analogs. Naunyn Schmiedebergs Arch. Pharmacol. 2002, 365, 457.
3. K. F. Foley, N. V. Cozzi,. Novel aminopropiophenones as potential antidepressants. Drug Dev. Res. 2003, 60, 252.
4. F. Schifano, A. Albanese, S. Fergus, J. L. Stair, P. Deluca, O. Corazza, Z. Davey, J. Corkery, H. Siemann, N. Scherbaum, M. Farre', M. Torrens, Z. Demetrovics, A. H. Ghodse,. Mephedrone (4-methylmethcathinone; 'meow meow'): chemical, pharmacological and clinical issues. Psychopharmacology (Berl) 2011, 214, 593.
5. AnonymousLand der Traeume Forum. 2011.
6. A. Winstock, L. Mitcheson, J. Ramsey, S. Davies, M. Puchnarewicz, J. Marsden,. Mephedrone: use, subjective effects and health risks. Addiction 2011, 106, 1991.
7. F. Westpfahl, T. Junge, U. Girreser, A. Jacobsen-Bauer, P. Roesner,. Badesalz für die Nase-Fluormethcathinon neu auf dem Drogenmarkt. Toxichem. Krimtech. 2010, 77, 84.
8. R. P. Archer,. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int. 2009, 185, 10.
9. E. Pawlik, G. Plasser, H. Mahler, T. Daldrup,. Studies on the phase I metabolism of the new designer drug 3-fluoromethcathinone using rabbit liver slices. Int. J. Legal Med. 2011. [Epub ahead of print]
10. H. H. Maurer, K. Pfleger, A. A. Weber,. Mass Spectral and GC Data of Drugs, Poisons, Pesticides, Pollutants and their Metabolites, Wiley-VCH: Weinheim, 2011.
11. H. H. Maurer,. Position of chromatographic techniques in screening for detection of drugs or poisons in clinical and forensic toxicology and/or doping control [review]. Clin. Chem. Lab. Med. 2004, 42, 1310.
12. A. H. Ewald, D. Ehlers, H. H. Maurer,. Metabolism and toxicological detection of the designer drug 4-chloro-2,5-dimethoxyamphetamine in rat urine using gas chromatography-mass spectrometry. Anal. Bioanal. Chem. 2008, 390, 1837.
13. S. E. Clarke,. In vitro assessment of human cytochrome P450. Xenobiotica 1998, 28, 1167.
14. C. L. Crespi, V. P. Miller,. The use of heterologously expressed drug metabolizing enzymes-state of the art and prospects for the future. Pharmacol. Ther. 1999, 84, 121.
15. K. Venkatakrishnan, L. L. von Moltke, M. H. Court, J. S. Harmatz, C. L. Crespi, D. J. Greenblatt,. Comparison between cytochrome P450 (CYP) content and relative activity approaches to scaling from cDNA-expressed CYPs to human liver microsomes: ratios of accessory proteins as sources of discrepancies between the approaches. Drug Metab. Dispos. 2000, 28, 1493.
16. K. Grime, R. J. Riley,. The impact of in vitro binding on in vitro-in vivo extrapolations, projections of metabolic clearance and clinical drug-drug interactions. Curr. Drug Metab. 2006, 7, 251.
17. M. R. Meyer, F. T. Peters, H. H. Maurer,. Automated mass spectral deconvolution and identification system for GC-MS screening for drugs, poisons, and metabolites in urine. Clin. Chem. 2010, 56, 575.
18. H. H. Maurer, K. Pfleger, A. A. Weber,. Mass Spectral Library of Drugs, Poisons, Pesticides, Pollutants and their Metabolites, Wiley-VCH: Weinheim, 2011.
19. F. Westphal, T. Junge, P. Rosner, G. Fritschi, B. Klein, U. Girreser,. Mass spectral and NMR spectral data of two new designer drugs with an alpha-aminophenone structure: 4'-Methyl-alpha-pyrrolidinohexanophenone and 4'-methyl-alpha-pyrrolidinobutyrophenone. Forensic Sci. Int. 2007, 169, 32.
20. F. W. McLafferty, F. Turecek,. Interpretation of Mass Spectra, University Science Books: Mill Valley, CA, 1993.
21. R. M. Smith, K. L. Busch,. Understanding Mass Spectra-A Basic Approach, Wiley: New York (NY), 1999.
22. R. A. de-Zeeuw, J. P. Franke, H. H. Maurer, K. Pfleger,. Gas Chromatographic Retention Indices of Toxicologically Relevant Substances and their Metabolites (Report of the DFG commission for clinical toxicological analysis, special issue of the TIAFT bulletin), VCH publishers: Weinheim, 1992.
23. P. Rosner, B. Quednow, U. Girreser, T. Junge,. Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs). Forensic Sci. Int. 2005, 148, 143.
24. D. K. Wissenbach, M. R. Meyer, D. Remane, A. A. Philipp, A. A. Weber, H. H. Maurer,. Drugs of abuse screening in urine as part of a metabolite-based LC-MS(n) screening concept. Anal. Bioanal. Chem. 2011, 400, 3481.
25. M. R. Meyer, F. T. Peters, H. H. Maurer,. The role of human hepatic cytochrome P450 isozymes in the metabolism of racemic 3,4-methylenedioxy- methamphetamine and its enantiomers. Drug Metab. Dispos. 2008, 36, 2345.
26. M. R. Meyer, F. T. Peters, H. H. Maurer,. Stereoselective differences in the cytochrome P450-dependent dealkylation and demethylenation of N-methyl-benzodioxolyl-butanamine (MBDB, Eden) enantiomers. Biochem. Pharmacol. 2009, 77, 1725.