Abstract
Studies are described on the metabolism and the toxicological analysis of the amphetamine-derived designer drug 4-chloro-2,5-dimethoxyamphetamine (DOC) in rat urine using gas chromatographic-mass spectrometric techniques. The metabolites identified indicated that DOC was metabolized by O-demethylation at position 2 or 5 of the phenyl ring partly followed by glucuronidation and/or sulfation. The authors’ systematic toxicological analysis procedure using full-scan gas chromatography-mass spectrometry after acid hydrolysis, liquid-liquid extraction and microwave-assisted acetylation allowed the detection of an intake of a dose of DOC in rat urine that corresponds to a common drug user’s dose. Assuming similar metabolism, the STA procedure described should be suitable as proof of an intake of DOC in human urine.
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References
Shulgin A (1991) Pihkal, a chemical love story. Transform, Berkley
Monte AP, Marona-Lewicka D, Parker MA, Wainscott DB, Nelson DL, Nichols DE (1996) J Med Chem 39:2953–2961
Neuvonen K, Neuvonen H, Fulop F (2006) Bioorg Med Chem Lett 16:3495–3498
Nelson DL, Lucaites VL, Wainscott DB, Glennon RA (1999) Naunyn Schmiedebergs Arch Pharmacol 359:1–6
Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA (1990) J Med Chem 33:1032–1036
Drug Enforcement Administration-Office of Forensic Sciences (2006) Microgram 39:137
Drug Enforcement Administration-Office of Forensic Sciences (2006) Microgram 39:72
Drug Enforcement Administration-Office of Forensic Sciences (2007) Microgram 40:42
Drug Enforcement Administration-Office of Forensic Sciences (2007) Microgram 40:93
Ewald AH, Fritschi G, Maurer HH (2006) J Mass Spectrom 41:1140–1148
Ewald AH, Fritschi G, Bork WR, Maurer HH (2006) J Mass Spectrom 41:487–498
Ewald AH, Fritschi G, Maurer HH (2007) J Chromatogr B 857:170–174
McKay AF, Ott WL, Taylor GW, Buchanan MN, Crooker JF (1950) Can J Res 28:683–688
Ewald AH, Peters FT, Weise M, Maurer HH (2005) J Chromatogr B 824:123–131
Maurer HH, Pfleger K, Weber AA (2007) Mass spectral library of drugs, poisons, pesticides, pollutants and their metabolites, 4th edn. Wiley-VCH, Weinheim
Maurer HH (2004) Clin Chem Lab Med 42:1310–1324
Theobald DS, Fehn S, Maurer HH (2005) J Mass Spectrom 40:105–116
Theobald DS, Staack RF, Puetz M, Maurer HH (2005) J Mass Spectrom 40:1157–1172
McLafferty FW, Turecek F (1993) Interpretation of mass spectra. University Science Books, Mill Valley
Smith RM, Busch KL (1999) Understanding mass spectra-a basic approach. Wiley, New York
Scorza MC, Carrau C, Silveira R, Zapata-Torres G, Cassels BK, Reyes-Parada M (1997) Biochem Pharmacol 54:1361–1369
Maurer HH, Pfleger K, Weber AA (2007) Mass spectral and GC data of drugs, poisons, pesticides, pollutants and their metabolites, 3rd edn. Wiley-VCH, Weinheim
Kovats E (1958) Helv Chim Acta 41:1915–1932
de-Zeeuw RA, Franke JP, Maurer HH, Pfleger K (1992) 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, Weinheim
Balikova M (2005) Forensic Sci Int 153:85–91
Beyer J, Ehlers D, Maurer HH (2006) Ther Drug Monit 28:568–575
Staack RF, Fritschi G, Maurer HH (2002) J Chromatogr B 773:35–46
Bickeboeller-Friedrich J, Maurer HH (2001) Ther Drug Monit 23:61–70
Acknowledgements
The authors would like to thank Johanna Schäning, Frank T. Peters, Christoph Sauer, Gabi Ulrich and Armin A. Weber for their suggestions and help.
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Ewald, A.H., Ehlers, D. & Maurer, H.H. Metabolism and toxicological detection of the designer drug 4-chloro-2,5-dimethoxyamphetamine in rat urine using gas chromatography-mass spectrometry. Anal Bioanal Chem 390, 1837–1842 (2008). https://doi.org/10.1007/s00216-008-1917-z
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DOI: https://doi.org/10.1007/s00216-008-1917-z