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Differentiation of regioisomeric fluoroamphetamine analogs by gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry

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Abstract

In recent years, a large number of clandestinely produced controlled-substance analogs (designer drugs) of amphetamine with high structural variety have been detected in forensic samples. Analytical differentiation of regioisomers is a significant issue in forensic drug analysis because, in most cases, legal controls are placed only on one or two of the three isomers. In this study, we used gas chromatography–mass spectrometry (GC–MS) and liquid chromatography–tandem mass spectrometry (LC–MS/MS) for the differentiation of regioisomers of fluoroamphetamine analogs (fluoroamphetamines and fluoromethamphetamines), which were synthesized in our laboratories. Free bases and their acylated and silylated derivatives were subjected to GC–MS analysis using DB-1ms, DB-5ms, and DB-17ms capillary columns. The separation of free bases was incomplete on all columns. Trifluoroacetyl derivatives of 3- and 4-positional isomers showed slight separation on DB-1ms and DB-5ms. On the other hand, trimethylsilyl derivatization enabled baseline separation of six fluoroamphetamine analogs on DB-1ms and DB-5ms columns, which was sufficient for unequivocal identification. For LC–MS/MS, a pentafluorophenyl column was able to separate six regioisomeric fluoroamphetamine analogs but a conventional C18 column could not achieve separation between 3- and 4-positional isomers. These results show that a suitable choice of derivatization and analytical columns allows the differentiation of regioisomeric fluoroamphetamine analogs.

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Acknowledgments

This work was supported in part by the R&D Program for Implementation of Anti-Crime and Anti-Terrorism Technologies for a Safe and Secure Society, Strategic Funds for the Promotion of Science and Technology of the Ministry of Education, Culture, Sports, Science, and Technology of Japan.

Conflict of interest

There are no financial or other relations that could lead to a conflict of interest.

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Authors and Affiliations

  1. National Research Institute of Police Science, 6-3-1 Kashiwanoha, Kashiwa, 277-0882, Japan

    Yukiko Nakazono, Kenji Tsujikawa, Kenji Kuwayama, Tatsuyuki Kanamori, Yuko T. Iwata & Hiroyuki Inoue

  2. Biochemical Toxicology Laboratory, Faculty of Pharmaceutical Sciences, Kobegakuin University, 1-1-3 Minatojima, Chuo-ku, Kobe, 650-8586, Japan

    Kazuna Miyamoto & Fumiyo Kasuya

  3. Hitec, Inc., 1-15-1 Benten, Chuo-ku, Chiba, 260-0045, Japan

    Yukiko Nakazono & Kazuna Miyamoto

Authors
  1. Yukiko Nakazono
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  2. Kenji Tsujikawa
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  3. Kenji Kuwayama
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  4. Tatsuyuki Kanamori
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  5. Yuko T. Iwata
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  6. Kazuna Miyamoto
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  7. Fumiyo Kasuya
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  8. Hiroyuki Inoue
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Correspondence to Hiroyuki Inoue.

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Nakazono, Y., Tsujikawa, K., Kuwayama, K. et al. Differentiation of regioisomeric fluoroamphetamine analogs by gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry. Forensic Toxicol 31, 241–250 (2013). https://doi.org/10.1007/s11419-013-0184-7

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  • DOI: https://doi.org/10.1007/s11419-013-0184-7

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