Forensic Toxicology

, Volume 34, Issue 1, pp 108–114 | Cite as

Three 25-NBOMe-type drugs, three other phenethylamine-type drugs (25I-NBMD, RH34, and escaline), eight cathinone derivatives, and a phencyclidine analog MMXE, newly identified in ingredients of drug products before they were sold on the drug market

  • Asuka Kaizaki-Mitsumoto
  • Naoki Noguchi
  • Saki Yamaguchi
  • Yuki Odanaka
  • Satoko Matsubayashi
  • Hiroki Kumamoto
  • Kiyoshi Fukuhara
  • Masahiko Funada
  • Kiyoshi Wada
  • Satoshi Numazawa
Original Article

Abstract

Twenty-two samples of ingredients of recreational drugs before being sold on the drug market obtained from a dubious drug dealer were analyzed by gas chromatography/mass spectrometry, high-resolution mass spectrometry, and nuclear magnetic resonance (NMR) spectroscopy. The present study showed 15 novel designer drugs, which have not been described in scientific literature. They included three NBOMe drugs 25H-NBOMe, 25D-NBOMe, and 25E-NBOMe, three other phenethylamine-type drugs 25I-NBMD, RH34, and escaline, eight cathinone derivatives 5-DBFPV, 3,4-MDPHP, 3,4-dimethyl-NEB, 3,4-dimethyl-α-ethylaminopentiophenone, 3,4-dimethyl-α-PVP, 4F-α-ethylaminopentiophenone, bk-IVP, and bk-IBP, and a phencyclidine derivative MMXE. In addition to the above novel compounds, known compounds such as 25I-NBOMe, ADB-CHIMINACA, 5F-ADB, and butane-1,4-diol were also identified from some samples. The electron ionization mass spectra, high-resolution data of molecular formulae, and NMR spectra presented in this article seem very useful for forensic toxicologists, who are obliged to identify new psychotropic drugs in any dubious products and/or human specimens.

Keywords

New 25-NBOMe-type designer drugs 5-DBFPV 3,4-MDPHP bk-IVP MMXE Identification of newly emerged psychotropic drugs 

Notes

Acknowledgments

This work was supported by JSPS KAKENHI Grant Number 15K18908. The authors are grateful to Mr. Atsushi Hosoya (a research collaborator) for his assistance obtaining drug samples.

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.
    Numazawa S (2013) The forefront of drug abuse—recent trends in illegal drug markets in Japan, 2012. The Showa University Journal of Pharmaceutical Sciences 4:13–25 (in Japanese with English abstract) Google Scholar
  2. 2.
    Scientific Working Group for the Analysis of Seized Drugs (2014) SWGDRUG MS library version 2.2. http://www.swgdrug.org/ms.htm. Accessed November 2014
  3. 3.
    Cayman Chemical (2014) Cayman spectral library. https://www.caymanchem.com/app/template/SpectralLibrary.vm. Accessed November 2014
  4. 4.
    Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products. Forensic Toxicol 32:105–115CrossRefGoogle Scholar
  5. 5.
    Poklis JL, Devers KG, Arbefeville EF, Pearson JM, Houston E, Poklis A (2014) Postmortem detection of 25I-NBOMe [2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine] in fluids and tissues determined by high performance liquid chromatography with tandem mass spectrometry from a traumatic death. Forensic Sci Int 234:e14–e20PubMedPubMedCentralCrossRefGoogle Scholar
  6. 6.
    Kueppers VB, Cooke CT (2015) 25I-NBOMe related death in Australia: a case report. Forensic Sci Int 249:e15–e18PubMedCrossRefGoogle Scholar
  7. 7.
    Suzuki J, Dekker MA, Valenti ES, Arbelo Cruz FA, Correa AM, Poklis JL, Poklis A (2015) Toxicities associated with NBOMe ingestion-a novel class of potent hallucinogens: a review of the literature. Psychosomatics 56:129–139PubMedCrossRefGoogle Scholar
  8. 8.
    Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (2015) Identification and quantitation of 5-fluoro-ADB-PINACA and MAB-CHMINACA in dubious herbal products. Forensic Toxicol 33:213–220CrossRefGoogle Scholar
  9. 9.
    Hasegawa K, Wurita A, Minakata K, Gonmori K, Yamagishi I, Nozawa H, Watanabe K, Suzuki O (2015) Identification and quantitation of 5-fluoro-ADB, one of the most dangerous synthetic cannabinoids, in the stomach contents and solid tissues of a human cadaver and in some herbal products. Forensic Toxicol 33:112–121CrossRefGoogle Scholar
  10. 10.
    Dahl SR, Olsen KM, Strand DH (2012) Determination of gamma-hydroxybutyrate (GHB), beta-hydroxybutyrate (BHB), pregabalin, 1,4-butane-diol (1,4BD) and gamma-butyrolactone (GBL) in whole blood and urine samples by UPLC-MSMS. J Chromatogr B 885/886:37–42CrossRefGoogle Scholar
  11. 11.
    Corazza O, Schifano F, Simonato P, Fergus S, Assi S, Stair J, Corkery J, Trincas G, Deluca P, Davey Z, Blaszko U, Demetrovics Z, Moskalewicz J, Farre M, Flesland L, Pasinetti M, Pezzolesi C, Pisarska A, Shapiro H, Siemann H, Skutle A, Enea A, di Melchiorre G, Sferrazza E, Torrens M, van der Kreeft P, Zummo D, Scherbaum N (2012) Phenomenon of new drugs on the Internet: the case of ketamine derivative methoxetamine. Hum Psychopharmacol Clin Exp 27:145–149CrossRefGoogle Scholar

Copyright information

© Japanese Association of Forensic Toxicology and Springer Japan 2015

Authors and Affiliations

  • Asuka Kaizaki-Mitsumoto
    • 1
  • Naoki Noguchi
    • 1
  • Saki Yamaguchi
    • 1
  • Yuki Odanaka
    • 2
  • Satoko Matsubayashi
    • 2
  • Hiroki Kumamoto
    • 3
  • Kiyoshi Fukuhara
    • 3
  • Masahiko Funada
    • 4
  • Kiyoshi Wada
    • 5
  • Satoshi Numazawa
    • 1
  1. 1.Division of Toxicology, Department of Pharmacology, Toxicology and TherapeuticsShowa University School of PharmacyShinagawa-kuJapan
  2. 2.Center for Instrumental AnalysisShowa University School of PharmacyTokyoJapan
  3. 3.Department of Medicinal and Industrial ChemistryShowa University School of PharmacyTokyoJapan
  4. 4.National Institute of Mental HealthNational Center of Neurology and PsychiatryKodairaJapan
  5. 5.Saitama Prefectural Psychiatric HospitalKitaadachi-gunJapan

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