Table of Contents
International Journal of Spectroscopy
Volume 2011, Article ID 318148, 12 pages
http://dx.doi.org/10.1155/2011/318148
Research Article

Fragmentation Pathways of Trifluoroacetyl Derivatives of Methamphetamine, Amphetamine, and Methylenedioxyphenylalkylamine Designer Drugs by Gas Chromatography/Mass Spectrometry

1Department of Legal Medicine, Showa University School of Medicine, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan
2Department of Forensic Medicine, Fukuoka University School of Medicine, 7-45-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan
3Department of Legal Medicine, Toho University School of Medicine, 5-21-16 Omorinishi, Ota-ku, Tokyo 143-8540, Japan
4Department of Legal Medicine, Nihon University School of Medicine, 30-1 Ohyaguchi-kamicho, Itabashi-ku, Tokyo 173-8610, Japan
5Department of Legal Medicine, Aichi Medical University School of Medicine, Nagakute-cho, Aichi 480-1195, Japan
6Department of Legal Medicine, Hamamatsu University School of Medicine, 1-20-1 Handayama, Higashi-ku, Hamamatsu 431-3192, Japan

Received 24 February 2011; Accepted 26 June 2011

Academic Editor: Stefan Schmatz

Copyright © 2011 Takeshi Kumazawa et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. V. Fineschi, F. Centini, E. Mazzeo, and E. Turillazzi, “Adam (MDMA) and Eve (MDEA) misuse: an immunohistochemical study on three fatal cases,” Forensic Science International, vol. 104, no. 1, pp. 65–74, 1999. View at Publisher · View at Google Scholar · View at Scopus
  2. N. Carter, G. N. Rutty, C. M. Milroy, and A. R. W. Forrest, “Deaths associated with MBDB misuse,” International Journal of Legal Medicine, vol. 113, no. 3, pp. 168–170, 2000. View at Publisher · View at Google Scholar · View at Scopus
  3. R. García-Repetto, E. Moreno, T. Soriano, C. Jurado, M. P. Giménez, and M. Menéndez, “Tissue concentrations of MDMA and its metabolite MDA in three fatal cases of overdose,” Forensic Science International, vol. 135, no. 2, pp. 110–114, 2003. View at Publisher · View at Google Scholar · View at Scopus
  4. J. L. Pilgrim, D. Gerostamoulos, O. H. Drummer, and M. Bollmann, “Involvement of amphetamines in sudden and unexpected death,” Journal of Forensic Sciences, vol. 54, no. 2, pp. 478–485, 2009. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  5. P. R. Paetsch, G. B. Baker, L. E. Caffaro, A. J. Greenshaw, G. A. Rauw, and R. T. Coutts, “Electron-capture gas chromatographic procedure for simultaneous determination of amphetamine and N-methylamphetamine,” Journal of Chromatography, vol. 573, no. 2, pp. 313–317, 1992. View at Publisher · View at Google Scholar · View at Scopus
  6. P. Marquet, E. Lacassie, C. Battu, H. Faubert, and G. Lachâtre, “Simultaneous determination of amphetamine and its analogs in human whole blood by gas chromatography-mass spectrometry,” Journal of Chromatography B, vol. 700, no. 1-2, pp. 77–82, 1997. View at Publisher · View at Google Scholar · View at Scopus
  7. F. T. Peters, S. Schaefer, R. F. Staack, T. Kraemer, and H. H. Maurer, “Screening for and validated quantification of amphetamines and of amphetamine- and piperazine-derived designer drugs in human blood plasma by gas chromatography/mass spectrometry,” Journal of Mass Spectrometry, vol. 38, no. 6, pp. 659–676, 2003. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  8. F. Moriya, “Accumulation of intravenously administered methamphetamine in stomach contents,” Forensic Toxicology, vol. 28, no. 1, pp. 43–46, 2010. View at Publisher · View at Google Scholar · View at Scopus
  9. G. Frison, L. Tedeschi, D. Favretto, A. Reheman, and S. D. Ferrara, “Gas chromatography/mass spectrometry determination of amphetamine-related drugs and ephedrines in plasma, urine and hair samples after derivatization with 2,2,2-trichloroethyl chloroformate,” Rapid Communications in Mass Spectrometry, vol. 19, no. 7, pp. 919–927, 2005. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  10. D. R. Knapp, Handbook of Analytical Derivatization Reactions, Wiley & Sons, New York, NY, USA, 1979.
  11. J. T. Cody and R. L. Foltz, “GC/MS analysis of body fluids for drugs of abuse,” in Forensic Applications of Mass Spectrometry, J. Yinon, Ed., pp. 2–59, CRC Press, Boca Raton, Fla, USA, 1995. View at Google Scholar
  12. W. Weinmann, M. Renz, S. Vogt, and S. Pollak, “Automated solid-phase extraction and two-step derivatisation for simultaneous analysis of basic illicit drugs in serum by GC/MS,” International Journal of Legal Medicine, vol. 113, no. 4, pp. 229–235, 2000. View at Google Scholar · View at Scopus
  13. M. Pujadas, S. Pichini, S. Poudevida et al., “Development and validation of a gas chromatography-mass spectrometry assay for hair analysis of amphetamine, methamphetamine and methylenedioxy derivatives,” Journal of Chromatography B, vol. 798, no. 2, pp. 249–255, 2003. View at Publisher · View at Google Scholar · View at Scopus
  14. J. L. Villamor, A. M. Bermejo, P. Fernández, and M. J. Tabernero, “A new GC-MS method for the determination of five amphetamines in human hair,” Journal of Analytical Toxicology, vol. 29, no. 2, pp. 135–139, 2005. View at Google Scholar · View at Scopus
  15. C. Hasegawa, T. Kumazawa, X. P. Lee et al., “Pipette tip solid-phase extraction and gas chromatography-mass spectrometry for the determination of methamphetamine and amphetamine in human whole blood,” Analytical and Bioanalytical Chemistry, vol. 389, no. 2, pp. 563–570, 2007. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  16. S. Lee, Y. Park, W. Yang et al., “Development of a reference material using methamphetamine abusers' hair samples for the determination of methamphetamine and amphetamine in hair,” Journal of Chromatography B, vol. 865, no. 1-2, pp. 33–39, 2008. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  17. K. Kudo, T. Ishida, W. Hikiji et al., “Construction of calibration-locking databases for rapid and reliable drug screening by gas chromatography-mass spectrometry,” Forensic Toxicology, vol. 27, no. 1, pp. 21–31, 2009. View at Publisher · View at Google Scholar · View at Scopus
  18. C. R. Clark, J. DeRuiter, A. K. Valaer, and F. T. Noggle, “GC-MS analysis of acylated derivatives of methamphetamine and regioisomeric phenethylamines,” Journal of Chromatographic Science, vol. 33, no. 9, pp. 485–492, 1995. View at Google Scholar
  19. C. R. Clark, J. DeRuiter, and F. T. Noggle, “Chromatographic and mass spectrometric methods for the differentiation of N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine from regioisomeric derivatives,” Journal of Chromatographic Science, vol. 34, no. 5, pp. 230–237, 1996. View at Google Scholar · View at Scopus
  20. B. Lindeke and A. K. Cho, “Specifically deuterated 1-phenyl-1-isopropylamines. Synthesis of deuterium (±)-amphetamine, (±)-α-methyltyramine,” Acta Pharmaceutica Suecica, vol. 9, no. 4, pp. 363–372, 1972. View at Google Scholar · View at Scopus
  21. D. B. Repke, D. K. Bates, and W. J. Ferguson, “Synthesis of dextroamphetamine sulfate and methamphetamine hydrochloride from D-phenylalanine,” Journal of Pharmaceutical Sciences, vol. 67, no. 8, pp. 1167–1168, 1978. View at Google Scholar · View at Scopus
  22. A. T. Shulgin and A. Shulgin, PiHKAL: A Chemical Love Story, Transform Press, Berkeley, Calif, USA, 1991.
  23. J. Y. Kim, K. S. Jung, M. K. Kim, J. I. Lee, and M. K. In, “Simultaneous determination of psychotropic phenylalkylamine derivatives in human hair by gas chromatography/mass spectrometry,” Rapid Communications in Mass Spectrometry, vol. 21, no. 11, pp. 1705–1720, 2007. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  24. C. Brede, I. Skjevrak, and H. Herikstad, “Determination of primary aromatic amines in water food simulant using solid-phase analytical derivatization followed by gas chromatography coupled with mass spectrometry,” Journal of Chromatography A, vol. 983, no. 1-2, pp. 35–42, 2003. View at Publisher · View at Google Scholar · View at Scopus
  25. H. Kataoka, “Derivatization reactions for the determination of amines by gas chromatography and their applications in environmental analysis,” Journal of Chromatography A, vol. 733, no. 1-2, pp. 19–34, 1996. View at Publisher · View at Google Scholar · View at Scopus
  26. D. G. I. Kingston, J. T. Bursey, and M. M. Bursey, “Intramolecular hydrogen transfer in mass spectra. II. The McLafferty rearrangement and related reactions,” Chemical Reviews, vol. 74, no. 2, pp. 215–242, 1974. View at Google Scholar · View at Scopus
  27. K. Zaitsu, M. Katagi, H. T. Kamata, A. Miki, and H. Tsuchihashi, “Discrimination and identification of regioisomeric β-keto analogues of 3,4-methylenedioxyamphetamines by gas chromatography-mass spectrometry,” Forensic Toxicology, vol. 26, no. 2, pp. 45–51, 2008. View at Publisher · View at Google Scholar · View at Scopus