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Forensic Toxicology

, Volume 34, Issue 1, pp 76–93 | Cite as

Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products

  • Takahiro Doi
  • Akiko Asada
  • Akihiro Takeda
  • Takaomi Tagami
  • Munehiro Katagi
  • Shuntaro Matsuta
  • Hiroe Kamata
  • Masami Kawaguchi
  • Yuka Satsuki
  • Yoshiyuki Sawabe
  • Hirotaka Obana
Original Article

Abstract

Recently, thienyl derivatives of cathinones have appeared on the market as new psychoactive substances (NPS). In this study, identification and characterization of 2-(pyrrolidin-1-yl)-1-(thiophen-2-yl)pentan-1-one (α-PVT), 2-(pyrrolidin-1-yl)-1-(thiophen-2-yl)butan-1-one (α-PBT), and their bromothienyl analogs disclosed in illicit products are described. In our analysis, some analogous compounds of α-PVT, which had a bromine substitution on the thiophene ring, were identified in the samples containing α-PVT; 1-(4-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one, 1-(5-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one, and 1-(4,5-dibromothiophen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one by comparing the analytical data with synthetic reference standards. We also observed 1-(4-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)butan-1-one and 1-(5-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)butan-1-one from a powder product, in which α-PBT was detected. The brominated α-PVTs were also found when overbrominated 1-(thiophen-2-yl)pentan-1-one reacted with pyrrolidine, and they are suspected to be the by-products of α-PVT synthesis. In Japan, cathinone derivatives with a phenyl group as the aromatic ring have been widely controlled by generic scheduling. To escape from such a regulation, analogs with different aromatic groups such as α-PVT and α-PBT appeared on the illicit market of psychoactive compounds. To our knowledge, this is the first report describing identification of α-PBT, and bromothienyl analogs of both α-PVT and α-PBT in illicit drug products. The synthetic method and analytical data shown in this study will be useful for identification of the thienyl derivatives of cathinone analogs.

Keywords

New cathinone derivatives α-PVT α-PBT Bromothienyl analogs New psychoactive substances (NPS) 

Notes

Acknowledgments

This study was partly supported by JSPS KAKENHI Grant No. 25860475 and 15K08834.

Compliance with ethical standards

Conflict of interest

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

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

References

  1. 1.
    Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2013) Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012. Forensic Toxicol 31:44–53CrossRefGoogle Scholar
  2. 2.
    Uemura N, Fukaya H, Kanai C, Yoshida M, Nakajima J, Takahashi M, Suzuki J, Moriyasu T, Nakae D (2014) Identification of a synthetic cannabinoid A-836339 as a novel compound found in a product. Forensic Toxicol 32:45–50CrossRefGoogle Scholar
  3. 3.
    Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products. Forensic Toxicol 31:223–240CrossRefGoogle Scholar
  4. 4.
    Zuba D, Geppert B, Sekuła K, Żaba C (2013) [1-(Tetrahydropyran-4-ylmethyl)-1H-indol-3-yl]-(2, 2, 3, 3-tetramethylcyclopropyl) methanone: a new synthetic cannabinoid identified on the drug market. Forensic Toxicol 31:281–291CrossRefGoogle Scholar
  5. 5.
    Leffler AM, Smith PB, de Armas A, Dorman FL (2014) The analytical investigation of synthetic street drugs containing cathinone analogs. Forensic Sci Int 234:50–56PubMedCrossRefGoogle Scholar
  6. 6.
    Fornal E, Stachniuk A, Wojtyla A (2013) LC-Q/TOF mass spectrometry data driven identification and spectroscopic characterisation of a new 3,4-methylenedioxy-N-benzyl cathinone (BMDP). J Pharm Biomed Anal 72:139–144PubMedCrossRefGoogle Scholar
  7. 7.
    Zaitsu K, Katagi M, Tsuchihashi H, Ishii A (2014) Recently abused synthetic cathinones, α-pyrrolidinophenone derivatives: a review of their pharmacology, acute toxicity, and metabolism. Forensic Toxicol 32:1–8CrossRefGoogle Scholar
  8. 8.
    Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2014) Changes in the prevalence of new psychoactive substances before and after the introduction of the generic scheduling of synthetic cannabinoids in Japan. Drug Test Anal 6:832–839PubMedCrossRefGoogle Scholar
  9. 9.
    Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products. Forensic Sci Int 227:21–32PubMedCrossRefGoogle Scholar
  10. 10.
    Asada A, Doi T, Takeda A, Tagami T, Kawaguchi M, Satsuki Y, Sawabe Y (2015) Identification of analogs of LY2183240 and the LY2183240 2′-isomer in herbal products. Forensic Toxicol 33:311–320CrossRefGoogle Scholar
  11. 11.
    Meltzer PC, Butler D, Deschamps JR, Madras BK (2006) 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: a promising class of monoamine uptake inhibitors. J Med Chem 49:1420–1432PubMedPubMedCentralCrossRefGoogle Scholar
  12. 12.
    Archer RP (2009) Fluoromethcathinone, a new substance of abuse. Forensic Sci Int 185:10–20PubMedCrossRefGoogle Scholar
  13. 13.
    Stojanovska N, Fu S, Tahtouh M, Kelly T, Beavis A, Kirkbride KP (2013) A review of impurity profiling and synthetic route of manufacture of methylamphetamine, 3,4-methylenedioxymethylamphetamine, amphetamine, dimethylamphetamine and p-methoxyamphetamine. Forensic Sci Int 224:8–26PubMedCrossRefGoogle Scholar
  14. 14.
    Zuba D (2012) Identification of cathinones and other active components of ‘legal highs’ by mass spectrometric methods. Trends Anal Chem 32:15–30CrossRefGoogle Scholar
  15. 15.
    Westphal F, Junge T, Girreser U, Greibl W, Doering C (2012) Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci Int 217:157–167PubMedCrossRefGoogle Scholar

Copyright information

© Japanese Association of Forensic Toxicology and Springer Japan 2015

Authors and Affiliations

  • Takahiro Doi
    • 1
  • Akiko Asada
    • 1
  • Akihiro Takeda
    • 1
  • Takaomi Tagami
    • 1
  • Munehiro Katagi
    • 2
  • Shuntaro Matsuta
    • 2
  • Hiroe Kamata
    • 2
  • Masami Kawaguchi
    • 1
  • Yuka Satsuki
    • 1
  • Yoshiyuki Sawabe
    • 1
  • Hirotaka Obana
    • 1
  1. 1.Department of Food, Drugs and EnvironmentOsaka Prefectural Institute of Public HealthOsakaJapan
  2. 2.Forensic Science LaboratoryOsaka Prefectural Police HeadquartersOsakaJapan

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