Summary
Native and derivatized β-cyclodextrins such as chiral stationary phases (CSP) were used for the simultaneous enantiomeric separation of four methylenedioxylated amphetamines (MDA, MDMA, MDEA and MBDB) by liquid chromatography. Fluorimetric detection was used in order to enhance sensitivity and selectivity. The mobile phase was, optimised by studying the influence of pH, triethylamine concentration, organic solvent type, column temperature and flow rate of the mobile phase. This method was validated by determining linearity, precision, accuracy, limits of detection and quantification, and was applied to the stereoselective analysis of illicit tablets (23 samples) and of human whole blood samples (spiked samples and two post-mortem cases). Whereas no significant deviation from a racemic ratio was observed in the tablets contents, the analysis of blood samples showed an enantioselective metabolism of MDMA.
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References
S. J. Peroutka, N. Engl. J. Med.317, 1542 (1987).
J. D. Wright, L. Pearl, BMJ300, 99 (1990).
C. Giroud, M. Augsburger, F. Sadeghipour, E. Varesio, J. L. Veuthey, L. Rivier, Praxis86, 510 (1997).
G. P. Dowling, E. T. McDonough III, R. O. Bost, JAMA257, 1615 (1987).
J. A. Henry, BMJ305, 5 (1992)
J. A. Henry, K. J. Jeffreys, S. Dawling, Lancet340, 384 (1992).
G. T. Tucker, M. S. Lennard, S. W. Ellis, H. F. Woods, A. K. Cho, Biomed. Pharmacol.47, 1151 (1994).
A. R. Green, A. J. Cross, G. M. Goodwin, Psychopharmacology119, 247 (1995).
F. Benazzi, M. Mazzoli, Lancet338, 1520 (1991).
F. Sadeghipour, C. Giroud., L. Rivier, J.-L. Veuthey, J. Chromatogr. A761, 71 (1997).
F. Sadeghipour, E. Varesio, C. Giround, L. Rivier, J.-L. Veuthey, Forensic Sci. Int.86, 1 (1997).
F. Sadeghipour, J.-L. Veuthey, J. Chromatogr. A787, 137 (1997).
R. C. Baselt, Disposition of toxic drugs and chemiscals in man, Mosbey Year Book, Chicago, 1989.
N. Weiner in A. G. Gilman, L. S. Goodman, Rall TW, Murad F (Editors), The pharmacological basis of therapeutics, Macmillan, New York: 1985, p. 177.
J. Gall, J. Pharm. Sci.66, 169 (1977).
K. M. Taylor, S. H. Snyder, Science168, 1487 (1970).
F. Schifano, Lancet338, 1335 (1991).
P. M. Whitacker-Azmitia, T. A. Aronson, Am. J. Psychiatry146, 119 (1989).
K. A. Moore, A. Mozayani, M. F. Fierro, A. Poklis, J. Forensic Sci.83, 111 (1996).
D. E. Nichols, J. Psychoactive Drugs18, 305 (1986).
M. W. F. Nielen, Selective on-line precolumn sample handling and trace enrichment in liquid chromatography, PhD Thesis, Free University of Amsterdam; 1987.
J. Osterloh, L. L. Belle, Amphetamines (Abused drugs monographs), 1990.
M. Lehrer, Clin. Lab. Med.10, 271 (1990).
H. J. P. Sieveret, Chirality6, 295 (1994).
H. L. Jin, T. E. Beesley, Chromatographia38, 595 (1994).
M. J. LeBelle, C. Savard, B. A. Dawson, D. B. Black, L. K. Katyal, F. Zrecek, A. W. By, Forensic Sci. Int.71, 215 (1995).
A. M. Rizzi, R. Hirz, S. Cladrowa-Runge, H. Jonsson, Chromatographia39, 131 (1994).
A. J. Bourque, I. S. Krull, J Chromatogr.537, 123 (1991).
F. T. Noggle, Jr., J. DeRuiter, C. R. Clark, J. Chromatogr. Sci.28, 529 (1990).
I. S. Lurie, R. F. X. Klein, T. A. Dal Cason, M. J. LeBelle, R. Brenneisen, R. Weinberger, Analytical Chemistry66(22), 4019 (1994).
D. M. Northrop, B. R. McCord, J. M. Butler, J. Cap. Elec.1(2). 158 (1994).
Z. Wang, Y.-L. Sun, Z.-P. Sun, J. Chromatogr. A735, 295 (1996).
E. Varesio, J.-L. Veuthey, J. Chromatogr. A717, 219 (1995).
H. K. Lim, Z. Su, R. L. Foltz, Biol. Mass Spectrom.22, 403 (1993).
H.-J. Gaus, Z. Z. Gögüs, K. Schmeer, B. Behnke, K.-A. Kovar, E. Bayer, J. Chromatogr. A735, 221 (1996).
S. Cladrowa-Runge, R. Hirz, E. Kenndler, A. Rizzi, J. Chromatogr. A710, 339 (1995).
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Sadeghipour, F., Veuthey, J.L. Enantiomeric separation of four methylenedioxylated amphetamines on β-cyclodextrin chiral stationary phases. Chromatographia 47, 285–290 (1998). https://doi.org/10.1007/BF02466533
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DOI: https://doi.org/10.1007/BF02466533