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Forensic Toxicology

, Volume 26, Issue 2, pp 45–51 | Cite as

Discrimination and identification of regioisomeric β-keto analogues of 3,4-methylenedioxyamphetamines by gas chromatography-mass spectrometry

  • Kei Zaitsu
  • Munehiro Katagi
  • Hiroe T. Kamata
  • Akihiro Miki
  • Hitoshi Tsuchihashi
Original Article

Abstract

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.

Keywords

Designer 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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References

  1. 1.
    Shulgin AT (1991) Pihkal: a chemical love story. Transform, BerkleyGoogle Scholar
  2. 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. 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
  4. 4.
    Rosner P, Quednow B, Girreser U, Junge T (2005) Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlledsubstance analogues (designer drugs). Forensic Sci Int 148:143–156PubMedCrossRefGoogle Scholar
  5. 5.
    Zaitsu K, Katagi M, Kamata T, Kamata H, Shima N, Tsuchihashi H, Hayashi T, Kuroki H, Matoba R (2008) Determination of a newly encountered designer drug “p-methoxyethylamphetamine” and its metabolites in human urine and blood. Forensic Sci Int 177:77–84PubMedCrossRefGoogle Scholar
  6. 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
  7. 7.
    Zaitsu K, Katagi M, Kamata H, Kamata T, Shima N, Miki A, Iwamura T, Tsuchihashi H (2008) Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J Mass Spectrom 43:528–534PubMedCrossRefGoogle Scholar
  8. 8.
    Kamata HT, Shima N, Zaitsu K, Kamata T, Miki A, Nishikawa M, Katagi M, Tsuchihashi H (2006) Metabolism of the recently encountered designer drug, methylone, in humans and rats. Xenobiotica 36:709–723PubMedCrossRefGoogle Scholar
  9. 9.
    McLafferty FW, Turecek F (1993) Interpretation of mass spectra, 4th edn. University Science Books, Mill ValleyGoogle Scholar
  10. 10.
    Smith RM, Busch KL (1999) Understanding mass spectra—a basic approach. Wiley, New YorkGoogle Scholar
  11. 11.
    Swantje B, Wolfram H, Peter R, Thomas J (2000) Synthesis of 2,3-and 3,4-methylenedioxyphenylalkylamines and their regioisomeric differentiation by mass spectral analysis using GC-MS-MS. Forensic Sci Int 114:139–153CrossRefGoogle Scholar
  12. 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. 13.
    Kovats ES (1965) Gas chromatographic characterization of organic substances in the retention index system. Adv Chromatogr 1:229–247Google Scholar

Copyright information

© Japanese Association of Forensic Toxicology 2008

Authors and Affiliations

  • Kei Zaitsu
    • 1
  • Munehiro Katagi
    • 1
  • Hiroe T. Kamata
    • 1
  • Akihiro Miki
    • 1
  • Hitoshi Tsuchihashi
    • 1
  1. 1.Forensic Science LaboratoryOsaka Prefectural Police HQChuo-ku, OsakaJapan

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