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Identification and quantification of synthetic cannabinoids in “spice-like” herbal mixtures: update of the German situation for the spring of 2015

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Abstract

In February 2015, 13 “spice-like” products, available on the German market, were analyzed. In total, eight different synthetic cannabinoids were identified by gas chromatography–mass spectrometry (GC–MS), namely 5-fluoro-AB-PINACA, AB-CHMINACA, AB-FUBINACA, 5-fluoro-PB-22, 5-fluoro-AMB, MDMB-CHMICA, EAM-2201 and STS-135. In most of the products (11/13), only one synthetic cannabinoid was identified, while two products contained two or three synthetic cannabinoids. For some of the compounds (5-fluoro-AB-PINACA, AB-CHMINACA, 5-fluoro-AMB) only insufficient physicochemical data are available in literature. To our knowledge MDMB-CHMICA (sometimes mistakenly referred to as MBMD-CHMINACA) was not described earlier in scientific literature, and, hence, an in-depth characterization of these compounds by nuclear magnetic resonance (NMR) spectroscopy, electron ionization–mass spectroscopy, electrospray ionization–tandem mass spectroscopy (ESI-MS/MS), infrared spectroscopy and ultraviolet spectroscopy was conducted for eight compounds. In addition, we developed an ESI-MS method for the direct quantification of synthetic cannabinoids in commercial smoking blends, without chromatographic separation. Quantification was achieved using methyl 3-(3-(1-naphthoyl)-1H-indol-1-yl)propionate as the internal standard with appropriate response factors. The total contents of synthetic cannabinoids in the investigated products ranged from 60 to 446 mg/g, while individual compounds ranged from 12 to 314 mg/g.

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References

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

    Article  PubMed  Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

  3. EMCDDA (2014) European drug report 2014: trends and developments, May 2014. http://www.emcdda.europa.eu/attachements.cfm/att_228272_EN_TDAT14001ENN.pdf. Accessed May 2015

  4. UNODC (2014) World drug report 2014, June 2014. http://www.unodc.org/documents/wdr2014/World_Drug_Report_2014_web.pdf. Accessed May 2015

  5. UNODC (2015) Decision 58/10 and 58/11. https://www.unodc.org/unodc/en/commissions/CND/Resolutions_Decisions/Resolutions-Decisions_2010-2019.html. Accessed Sept 2015

  6. 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 6:832–839

    Article  PubMed  CAS  Google Scholar 

  7. 28. BtMÄndV 2014, 13. December 2014. http://www.bgbl.de/banzxaver/bgbl/start.xav?start=%2F%2F*%5B%40attr_id%3D’bgbl104s0028.pdf’%5D#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl114s1999.pdf%27%5D__1427399651317. Accessed May 2015

  8. EU-Court (2014) Judgment of the court (Fourth Chamber), 10 July 2014. Medicinal products for human use. Joined cases C-358/13 and C-181/14. http://curia.europa.eu/juris/liste.jsf?language=de&num=C-358/13. Accessed May 2015

  9. Bundesgerichtshof (2015) StR 302/13. 14. January 2015. http://juris.bundesgerichtshof.de/cgi-bin/rechtsprechung/document.py?Gericht=bgh&Art=en&nr=70354&pos=0&anz=1. Accessed May 2015

  10. SWGDRUG (2014) SWGDRUG mass spectral library. http://www.swgdrug.org/ms.htm. Accessed Feb 2015

  11. Cayman Chemical (2014) Cayman spectral library. https://www.caymanchem.com/app/template/SpectralLibrary.vm. Accessed Feb 2015

  12. Lovett DP, Yanes EG, Herbelin TW, Knoerzer TA, Levisky JA (2013) Structure elucidation and identification of a common metabolite for naphthoylindole-based synthetic cannabinoids using LC–TOF and comparison to a synthetic reference standard. Forensic Sci Int 226:81–87

    Article  PubMed  CAS  Google Scholar 

  13. Langer N, Lindigkeit R, Schiebel HM, Ernst L, Beuerle T (2014) Identification and quantification of synthetic cannabinoids in ‘spice-like’ herbal mixtures: a snapshot of the German situation in the autumn of 2012. Drug Test Anal 6:59–71

    Article  PubMed  CAS  Google Scholar 

  14. Wurita A, Hasegawa K, Minakata K, Watanabe K, Suzuki O (2014) A large amount of new designer drug diphenidine coexisting with a synthetic cannabinoid 5-fluoro-AB-PINACA found in a dubious herbal product. Forensic Toxicol 32:331–337

    Article  CAS  Google Scholar 

  15. Wohlfarth A, Castaneto MS, Zhu M, Pang S, Scheidweiler KB, Kronstrand R, Huestis MA (2015) Pentylindole/pentylindazole synthetic cannabinoids and their 5-fluoro analogs produce different primary metabolites: metabolite profiling for AB-PINACA and 5F-AB-PINACA. AAPS J 17:660–677

    Article  PubMed  CAS  Google Scholar 

  16. Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (2015) Postmortem distribution of AB-CHMINACA, 5-fluoro-AMB, and diphenidine in body fluids and solid tissues in a fatal poisoning case: usefulness of adipose tissue for detection of the drugs in unchanged forms. Forensic Toxicol 33:45–53

    Article  CAS  Google Scholar 

  17. Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T (2014) Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol 32:266–281

    Article  CAS  Google Scholar 

  18. Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T (2015) A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N-OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products. Forensic Toxicol 33:244–259

    Article  PubMed  CAS  PubMed Central  Google Scholar 

  19. Takayama T, Suzuki M, Todoroki K, Inoue K, Min JZ, Kikura-Hanajiri R, Goda Y, Toyo'oka T (2014) UPLC/ESI–MS/MS-based determination of metabolism of several new illicit drugs, ADB-FUBINACA, AB-FUBINACA, AB-PINACA, QUPIC, 5F-QUPIC and α-PVT, by human liver microsome. Biomed Chromatogr 28:831–838

    Article  PubMed  CAS  Google Scholar 

  20. Uchiyama N, Matsuda S, Wakana D, Kikura-Hanajiri R, Goda Y (2013) New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as designer drugs in illegal products. Forensic Toxicol 31:93–100

    Article  CAS  Google Scholar 

  21. Chung H, Choi H, Heo S, Kim E, Lee J (2014) Synthetic cannabinoids abused in South Korea: drug identifications by the National Forensic Service from 2009 to June 2013. Forensic Toxicol 32:82–88

    Article  CAS  Google Scholar 

  22. Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y (2013) Analytical characterization of some synthetic cannabinoids, derivatives of indole-3-carboxylic acid. Forensic Sci Int 232:1–10

    Article  PubMed  CAS  Google Scholar 

  23. Behonick G, Shanks KG, Firchau DJ, Mathur G, Lynch CF, Nashelsky M, Jaskierny DJ, Meroueh C (2014) Four postmortem case reports with quantitative detection of the synthetic cannabinoid, 5F-PB-22. J Anal Toxicol 38:559–562

    Article  PubMed  PubMed Central  Google Scholar 

  24. Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RE, Wu KK (2009) Indazole derivatives as CB1 receptor modulators and their preparation and use in treatment of diseases. Patent WO/2009/106980, Sept 2009

  25. Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M (2015) Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135. Chem Neurosci 6:1445–1458

    Article  CAS  Google Scholar 

  26. Uchiyama N, Matsuda S, Wakana D, 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 227:21–32

    Article  PubMed  CAS  Google Scholar 

  27. Musah RA, Domin MA, Walling MA, Shepard JRE (2012) Rapid identification of synthetic cannabinoids in herbal samples via direct analysis in real time mass spectrometry. Rapid Commun Mass Spectrom 26:1109–1114

    Article  PubMed  CAS  Google Scholar 

  28. Grange AH, Sovocool G (2011) Detection of illicit drugs on surfaces using direct analysis in real time (DART) time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 25:1271–1281

    Article  PubMed  CAS  Google Scholar 

  29. Lesiak AD, Musah RA, Domin MA, Shepard JRE (2014) DART-MS as a preliminary screening method for “herbal incense”: chemical analysis of synthetic cannabinoids. J Forensic Sci 59:337–343

    Article  PubMed  CAS  Google Scholar 

  30. Moosmann B, Angerer V, Auwärter V (2015) Inhomogeneities in herbal mixtures: a serious risk for consumers. Forensic Toxicol 33:54–60

    Article  Google Scholar 

  31. Seely KA, Prather PL, James LP, Moran JH (2011) Marijuana-based drugs: innovative therapeutics or designer drugs of abuse? Mol Interv 11:36–51

    Article  PubMed  CAS  PubMed Central  Google Scholar 

  32. Ogata J, Uchiyama N, Kikura-Hanajiri R, Goda Y (2013) DNA sequence analyses of blended herbal products including synthetic cannabinoids as designer drugs. Forensic Sci Int 227:33–41

    Article  PubMed  CAS  Google Scholar 

  33. Simolka K, Lindigkeit R, Schiebel H-M, Papke U, Ernst L, Beuerle T (2012) Analysis of synthetic cannabinoids in “spice-like” herbal highs: snapshot of the German market in summer 2011. Anal Bioanal Chem 404:157–171

    Article  PubMed  CAS  Google Scholar 

  34. Ernst L, Krüger K, Lindigkeit R, Schiebel H-M, Beuerle T (2012) Synthetic cannabinoids in “spice-like” herbal blends: first appearance of JWH-307 and recurrence of JWH-018 on the German market. Forensic Sci Int 222:216–222

    Article  PubMed  CAS  Google Scholar 

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Acknowledgments

This work was supported by Zentrales Innovationsprogramm Mittelstand (ZIM) des Bundesministeriums für Wirtschaft und Energie (BMWI) FKZ: KF31565015K3. The authors express their gratitude to Lisa Sieverling, Judith Carla Schürmann and Kerstin Ollenborger for their helpful assistance.

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Correspondence to Till Beuerle.

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Langer, N., Lindigkeit, R., Schiebel, HM. et al. Identification and quantification of synthetic cannabinoids in “spice-like” herbal mixtures: update of the German situation for the spring of 2015. Forensic Toxicol 34, 94–107 (2016). https://doi.org/10.1007/s11419-015-0292-7

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