Skip to main content

Advertisement

Log in

Simultaneous analysis of synthetic cannabinoids in the materials seized during drug trafficking using GC-MS

  • Original Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

A rapid and simple gas chromatography–mass spectrometry (GC-MS) method was developed and validated to identify and quantify synthetic cannabinoids in the materials seized during drug trafficking. Accuracy and reproducibility of the method were improved by using deuterated JWH-018 and JWH-073 as internal standards. Validation results of the GC-MS method showed that it was suitable for simultaneous qualitative and quantitative analyses of synthetic cannabinoids, and we analyzed synthetic cannabinoids in seized materials using the validated GC-MS method. As a result of the analysis, ten species of synthetic cannabinoids were identified in dried leaves (n = 40), bulk powders (n = 6), and tablets (n = 14) seized in Korea during 2009–2012, as a single ingredient or as a mixture with other active co-ingredients. JWH-018 and JWH-073 were the most frequently identified compounds in the seized materials. Synthetic cannabinoids in the dried leaves showed broad concentration ranges, which may cause unexpected toxicity to abusers. The bulk powders were considered as raw materials used to prepare legal highs, and they contained single ingredient of JWH-073, JWH-019, or JWH-250 with the purity over 70 %. In contrast, JWH-018 and JWH-073 contents in the tablets were 7.1–13.8 and 3.0–10.2 mg/g, respectively. Relatively low contents in the tablets suggest that the synthetic cannabinoids may have been added to the tablets as supplements to other active co-ingredients.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. UNODC (2011) World drug report 2011. United Nations Office of Drugs and Crime (UNODC), Vienna

  2. Aung MM, Griffin G, Huffman JW, Wu MJ, Keel C, Yang B, Showalter VM, Abood ME (2000) Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug Alcohol Depend 60:133–140

    Article  CAS  Google Scholar 

  3. Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR (2005) 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg Med Chem Lett 15:4110–4113

    Article  CAS  Google Scholar 

  4. Auwärter V, Dresen S, Weinmann W, Müller M, Pütz M, Fereirós N (2009) “Spice” and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832–837

    Article  Google Scholar 

  5. Nakajima J, Takahashi M, Seto T, Kanai C, Suzuki J, Yoshida M, Hamano T (2011) Identification and quantitation of two benzylindoles AM-694 and (4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone, and three cannabimimetic naphthoylindoles JWH-210, JWH-122, and JWH-019 as adulterants in illegal products obtained via the internet. Forensic Toxicol 29:95–110

    Article  CAS  Google Scholar 

  6. Nakajima J, Takahashi M, Seto T, Suzuki J (2011) Identification and quantitation of cannabimimetic compound JWH-250 as an adulterant in products obtained via the internet. Forensic Toxicol 29:51–55

    Article  CAS  Google Scholar 

  7. Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2011) Identification and quantitation of two canabimimetic phenylacetylindoles JWH-251 and JWH-250, and four cannabimimetic naphthoylindoles JWH-081, JWH-015, JWH-200, and JWH-073 as designer drugs in illegal products. Forensic Toxicol 29:25–37

    Article  CAS  Google Scholar 

  8. Nakajima J, Takahashi M, Nonaka R, Seto T, Suzuki J, Yoshida M, Kanai C, Hamano T (2011) Identification and quantitation of a benzoylindole(2-methoxyphenyl)(1-pentyl-1H-indole-3-yl)-(naphthalene-1-yl)methanone (AM-2201) found in illegal products obtained via the internet and their cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays. Forensic Toxicol 29:132–141

    Article  CAS  Google Scholar 

  9. Ernst L, Schiebel HM, Theuring C, Lindigkeit R, Beuerle T (2011) Identification and characterization of JWH-122 used as new ingredient in “Spice-like” herbal incenses. Forensic Sci Int 208:e31–e35

    Article  CAS  Google Scholar 

  10. Moosmann B, Kneisel S, Girreser U, Brecht V, Westphal F, Auwärter V (2012) Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1H-indol-3yl]-(4-methylnaphthalen-1-yl)methanone using GC-MS, NMR analysis and a flash chromatography system. Forensic Sci Int 220:e17–e22

    Google Scholar 

  11. Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Paloás J, Balla J (2012) Detection and identification of the new potential synthetic cannabinoids 1-pentyl-3-(2-indobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary. Forensic Sci Int 214:27–32

    Article  CAS  Google Scholar 

  12. Hillebrand J, Olszewski D, Sedefov R (2010) Legal highs on the internet. Subst Use Misuse 45:330–340

    Article  Google Scholar 

  13. Ashton JC (2012) Synthetic cannabinoids as drugs of abuse. Curr Drug Abuse Rev 5:158–168

    Article  CAS  Google Scholar 

  14. EMCDDA (2009) Thematic papers: understanding the “Spice” phenomenon. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA), Lisbon

  15. Zimmermann US, Winkelmann PR, Pilhatsch M, Nees JA, Spanagel R, Schulz K (2009) Withdrawal phenomena and dependence syndrome after the consumption of “spice gold”. Dtsch Arztebl Int 106:464–467

    Google Scholar 

  16. Schneir AB, Baumbacher T (2012) Convulsions associated with the use of a synthetic cannabinoid product. J Med Toxicol 8:62–64

    Article  Google Scholar 

  17. Lapoint J, James LP, Moran CL, Nelson LS, Hoffman RS, Moran JH (2011) Severe toxicity following synthetic cannabinoid ingestion. Clin Toxicol (Phila) 49:760–764

    Article  CAS  Google Scholar 

  18. Wissenbach DK, Meyer MR, Remane D, Philipp AA, Weber AA, Maurer HH (2011) Drugs of abuse screening in urine as part of a metabolite-based LC-MS screening concept. Anal Bioanal Chem 400:3481–3489

    Article  CAS  Google Scholar 

  19. Lindigkeit R, Boehme A, Eiserloh I, Luebbecke M, Wiggermann M (2009) Spice: a never ending story? Forensic Sci Int 191:58–63

    Article  CAS  Google Scholar 

  20. Zuba D, Byrska B, Maciow M (2011) Comparison of “herbal highs” composition. Anal Bioanal Chem 400:119–126

    Article  CAS  Google Scholar 

  21. Wiskerke J, Stoop N, Schetters D, Schoffelmeer A, Pattij T (2011) Cannabinoid CB1 receptor activation mediates the opposing effects of amphetamine on impulsive action and impulsive choice. PLoS One. doi:10.1371/journal.pone.0025856

  22. Fernández-Ruiz J, Hernández M, Ramos JA (2010) Cannabinoid–dopamine interaction in the pathophysiology and treatment of CNS disorders. CNS Neurosci Ther 16:e72–e91

    Article  Google Scholar 

Download references

Acknowledgments

This study was supported by funding from the National R&D program of the Ministry of Education, Science and Technology (2012-0009836) and the National Forensic Service of Korea.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jaesin Lee.

Additional information

Published in the special paper collection Forensic Toxicology with guest editors Kazuhito Watanabe and Satoshi Chinaka.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Choi, H., Heo, S., Choe, S. et al. Simultaneous analysis of synthetic cannabinoids in the materials seized during drug trafficking using GC-MS. Anal Bioanal Chem 405, 3937–3944 (2013). https://doi.org/10.1007/s00216-012-6560-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-012-6560-z

Keywords

Navigation