Discrimination and identification of regioisomeric β-keto analogues of 3,4-methylenedioxyamphetamines by gas chromatography-mass spectrometry
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Very recently, β-keto derivatives of 3,4-methylenedioxyamphetamines (MDAs) have appeared on the illicit drug market. In the present study, we synthesized three isomers of β-keto derivatives of MDAs, 2-methylamino-1-(3,4-methylenedioxyphenyl)butan-1-one (bk-MBDB), 2-ethylamino-1-(3,4-methylenedioxyphenyl) propan-1-one (bk-MDEA), and 2-dimethylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (bk-MDDMA), and measured their electron ionization mass spectra without and with trifluoroacetyl (TFA) derivatization using gas chromatography-mass spectrometry (GC-MS). Although the spectral profiles of the three isomers were very similar to each other in both the free and TFA-derivatized forms, there were characteristic peaks at m/z 44 and 140, for bk-MDEA without and with TFA derivatization, respectively; a peak at m/z 110 for bk-MBDB-TFA was also characteristic. These peaks are useful for discrimination of an isomer from others. All isomers could be well separated in both free and TFA-derivatized forms using a slightly polar fused-silica capillary GC column DB-5MS. The present data are likely to be very useful for actual identification and quantitation of β-keto analogues of MDAs by GC-MS, because abuse of these materials is expected to spread worldwide in the near future.
KeywordsDesigner drug β-Ketone analogue 2-Methylamino-1-(3,4-methylenedioxyphenyl)butan-1-one 2-Ethylamino-1-(3,4-methylenedioxyphenyl)propan-1-one 2-Dimethylamino-1-(3,4-methylenedioxyphenyl)propan-1-one GC-MS
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- 1.Shulgin AT (1991) Pihkal: a chemical love story. Transform, BerkleyGoogle Scholar
- 2.Ellenhorn MJ (1997) Amphetamines and designer drugs. In: Ellenhorn MJ (ed) Ellenhorn’s medical toxicology, 2nd edn. Williams and Wilkins, Baltimore, pp 340–355Google Scholar
- 3.Koper C, Ali-Tolppa E, Bozenko JS Jr, Dufey V, Puetz M, Weyermann C, Zrcek F (2005) Identification of a new amphetamine type stimulant: 3,4-methylenedioxy-N-(2-hydroxyethyl)amphetamine (MDHOET). Microgram J 3:166–174Google Scholar
- 6.Kamata HT, Shima N, Zaitsu K, Kamata T, Nishikawa M, Katagi M, Miki A, Tsuchihashi H (2007) Simultaneous analysis of new designer drug, methylone, and its metabolites in urine by gas chromatography-mass spectrometry and liquid chromatography-electrospray ionization mass spectrometry. Jpn J Forensic Sci Technol 12:97–106CrossRefGoogle Scholar
- 9.McLafferty FW, Turecek F (1993) Interpretation of mass spectra, 4th edn. University Science Books, Mill ValleyGoogle Scholar
- 10.Smith RM, Busch KL (1999) Understanding mass spectra—a basic approach. Wiley, New YorkGoogle Scholar
- 12.Clark CR, DeRuiter J, Noggle FT (1996) Chromatographic and mass spectrometric methods for the differentiation of N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine from regioisomeric derivatives. J Chromatogr Sci 34:230–237Google Scholar
- 13.Kovats ES (1965) Gas chromatographic characterization of organic substances in the retention index system. Adv Chromatogr 1:229–247Google Scholar