Synthetic Cannabinoids 5F-QUPIC and MDMB-CHMICA in Plant Material – Identification and Quantification by Gas Chromatography – Mass Spectrometry (GC-MS), Nuclear Magnetic Resonance (NMR), and High-Performance Liquid Chromatography with Diode Array Detection (HPLC-DAD)

References

• Angerer, V., S. Jacobi, F. Franz, V. Auwärter, and J. Pietsch. 2017. Three fatalities associated with the synthetic cannabinoids 5F-ADB, 5F-PB-22, and AB-CHMINACA. Forensic Science International 281: E9–E15. doi:10.1016/j.forsciint.2017.10.042.
   PubMed Web of Science ®Google Scholar
• Behonick, G., K. Shanks, D. Firchau, G. Mathur, C. Lynch, M. Nashelsky, D. Jaskierny, and C. Meroueh. 2014. Four postmortem case reports with quantitative detection of the synthetic cannabinoid, 5F-PB-22. Journal of Analytical Toxicology 38(8):559–62. doi:10.1093/jat/bku048.
   PubMed Web of Science ®Google Scholar
• Buchler, I., M. Hayes, S. Hegde, S. Hockerman, D. Jones, S. Kortum, J. Rico, R. Tenbrink, and K. Wu. 2009. Indazole derivatives as CB1 receptor modulators and their preparation and use in treatment of diseases. Patent WO/2009/106980.
   Google Scholar
• Buser, G., R. R. Gerona, B. Z. Horowitz, K. P. Vian, M. L. Troxell, R. G. Hendrickson, D. C. Houghton, D. Rozansky, S. W. Su, and R. F. Leman. 2014. Acute kidney injury associated with smoking synthetic cannabinoid. Clinical Toxicology (Philadelphia, PA) 52 (7):664–73. doi:10.3109/15563650.2014.932365.
   PubMed Web of Science ®Google Scholar
• Chemical, C., and C. Spectral Library. 2018. https://www.caymanchem.com/forensics/publications/csl.
   Google Scholar
• Clark, B., J. Georgekutty, and C. Berul. 2015. Myocardial ischemia secondary to synthetic cannabinoid (K2) use in pediatric patients. The Journal of Pediatrics 167 (3):757–61. doi:10.1016/j.jpeds.2015.06.001.
   PubMed Web of Science ®Google Scholar
• European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). 2009. Forensic identification, pharmacology and toxicology of synthetic cannabinoids. In: Understanding the ‘Spice’ phenomenon. https://www.emcdda.europa.eu/publications/thematic-papers/understanding-spice-phenomenon_en
   Google Scholar
• European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). 2016. EMCDDA-Europol Joint Report on a new psychoactive substance: Methyl 2-[[1-(cyclohexylmethyl)indole-3-carbonyl]amino]-3,3-dimethylbutanoate (MDMB-CHMICA). https://www.emcdda.europa.eu/system/files/publications/2873/2016.4528_WEB.pdf
   Google Scholar
• Expert Committee on Drug Dependence (ECDD). 2017. 5F-PB-22. Critical Review Report. Agenda Item 4.12. https://www.who.int/medicines/access/controlled-substances/CriticalReview_5FPB22.pdf?ua=1
   Google Scholar
• Freeman, M. J., D. Z. Rose, M. A. Myers, C. L. Gooch, A. C. Bozeman, and W. S. Burgin. 2013. Ischemic stroke after use of the synthetic marijuana “spice”. Neurology 81 (24):2090–3. doi:10.1212/01.wnl.0000437297.05570.a2.
   PubMed Web of Science ®Google Scholar
• Fujiwara, M., and N. Egashira. 2004. New perspectives in the studies on endocannabinoid and cannabis: Abnormal behaviors associate with CB1 cannabinoid receptor and development of therapeutic application. Journal of Pharmacological Sciences 96 (4):362–6. doi:10.1254/jphs.FMJ04003X2.
   PubMed Web of Science ®Google Scholar
• Fulmer, G., A. Miller, N. Sherden, H. Gottlieb, A. Nudelman, B. Stoltz, J. Bercaw, and K. Goldberg. 2010. NMR chemical shifts of trace impurities: Common laboratory solvents, organics, and gases in deuterated solvents relevant to the organometallic chemist. Organometallics 29 (9):2176–9. doi:10.1021/om100106e.
   Web of Science ®Google Scholar
• Giorgetti, A., L. Mogler, S. Halter, B. Haschimi, A. Alt, D. Rentsch, B. Schmidt, V. Thoma, S. Vogt, and V. Auwärter. 2020. Four cases of death involving the novel synthetic cannabinoid 5F‐Cumyl‐PEGACLONE. Forensic Toxicology 38 (2):314–26. doi:10.1007/s11419-019-00514-w.
   Web of Science ®Google Scholar
• Gottlieb, H. E., V. Kotlyar, and A. Nudelman. 1997. NMR chemical shifts of common laboratory solvents as trace impurities. The Journal of Organic Chemistry 62 (21):7512–5. doi:10.1021/jo971176v.
   PubMed Web of Science ®Google Scholar
• Harris, C., and A. Brown. 2013. Synthetic cannabinoid intoxication: A case series and review. The Journal of Emergency Medicine 44 (2):360–6. doi:10.1016/j.jemermed. 2012.07.061.
   PubMed Web of Science ®Google Scholar
• Hermanns-Clausen, M., S. Kneisel, M. Hutter, B. Szabo, and V. Auwärter. 2013. Acute intoxication by synthetic cannabinoids-four case reports. Drug Testing and Analysis 5 (9–10):790–4. doi:10.1002/dta.1483.
   PubMed Web of Science ®Google Scholar
• Hess, C., C. Schoeder, T. Pillaiyar, B. Madea, and C. Müller. 2016. Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice. Forensic Toxicology 34:329–43. doi:10.1007/s11419-016-0320-2.
   PubMed Web of Science ®Google Scholar
• Hill, S., J. Najafi, M. Dunn, P. Acheampong, A. Kamour, J. Grundlingh, P. G. Blain, and S. H. L. Thomas. 2016. Clinical toxicity following analytically confirmed use of the synthetic cannabinoid receptor agonist MDMB-CHMICA. A report from the identification of novel psychoactive substances (IONA) study. Clinical Toxicology (Philadelphia, PA) 54 (8):638–43. doi:10.1080/15563650.2016.1190980.
   PubMed Web of Science ®Google Scholar
• Kovács, K., É. Kereszty, R. Berkecz, L. Tiszlavicz, É. Sija, T. Körmöczi, N. Jenei, H. Révész-Schmehl, and L. Institóris. 2019. Fatal intoxication of a regular drug user following N-ethyl-hexedrone and ADB-FUBINACA consumption. Journal of Forensic and Legal Medicine 65:92–100. doi:10.1016/j.jflm.2019.04.012.
   PubMed Web of Science ®Google Scholar
• Langer, N., R. Lindigkeit, H. Schiebel, U. Papke, L. Ernst, and T. Beuerle. 2016. Identification and quantification of synthetic cannabinoids in “spice-like” herbal mixtures: Update of the German situation for the spring of 2015. Forensic Toxicology 34 (1):94–107. doi:10.1007/s11419-015-0292-7.
   Web of Science ®Google Scholar
• Locatelli, C., D. Lonati, and V. Petrolini. 2020. New drugs of abuse and cardiovascular function. In Brain and heart dynamics, ed. S. Govoni, P. Politi, and E. Vanoli, 843–68. Cham: Springer. doi:10.1007/978-3-030-28008-6_55.
   Google Scholar
• Manera, C., T. Tuccinardi, and A. Martinelli. 2008. Indoles and related compounds as cannabinoid ligands. Mini Reviews in Medicinal Chemistry 8 (4):370–87. doi:10.2174/138955708783955935.
   PubMed Web of Science ®Google Scholar
• Mir, A., A. Obafemi, A. Young, and C. Kane. 2011. Myocardial infarction associated with use of the synthetic cannabinoid K2. Pediatrics 128 (6):e1622–7. doi:10.1542/peds.2010-3823.
   PubMed Web of Science ®Google Scholar
• Morrow, P. L., S. Stables, K. Kesha, R. Tse, D. Kappatos, R. Pandey, S. Russell, O. Linsell, M. J. McCarthy, A. Spark, et al. 2020. An outbreak of deaths associated with AMB-FUBINACA in Auckland NZ. EClinical Medicine 25:100460. doi:10.1016/j.eclinm.2020.100460.
   PubMedGoogle Scholar
• Penn, H. J., L. Langman, D. Unold, J. Shields, and J. Nichols. 2011. Detection of synthetic cannabinoids in herbal incense products. Clinical Biochemistry 44 (13):1163–5. doi:10.1016/j.clinbiochem.2011.06.078.
   PubMed Web of Science ®Google Scholar
• Seely, K., J. Lapoint, J. Moran, and L. Fattore. 2012. Spice drugs are more than harmless herbal blends: A review of the pharmacology and toxicology of synthetic cannabinoids. Progress in Neuro-Psychopharmacology & Biological Psychiatry 39 (2):234–43. doi:10.1016/j.pnpbp.2012.04.017.
   PubMed Web of Science ®Google Scholar
• Thomas, B. F., T. W. Lefever, R. A. Cortes, M. Grabenauer, A. L. Kovach, A. O. Cox, P. R. Patel, G. T. Pollard, J. A. Marusich, R. C. Kevin, et al. 2017. Thermolytic degradation of synthetic cannabinoids: Chemical exposures and pharmacological consequences. The Journal of Pharmacology and Experimental Therapeutics 361 (1):162–71. doi:10.1124/jpet.116.238717.
   PubMed Web of Science ®Google Scholar
• Tsujikawa, K., T. Yamamuro, K. Kuwayama, T. Kanamori, T. Iwata, and H. Inoue. 2014. Thermal degradation of a new synthetic cannabinoid QUPIC during analysis by gas chromatography-mass spectrometry. Forensic Toxicology 32 (2):201–7. doi:10.1007/s11419-013-0221-6.
   Web of Science ®Google Scholar
• Uchiyama, N., S. Matsuda, M. Kawamura, R. Kikura-Hanajiri, and Y. Goda. 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 a-PVT and an opioid receptor agonist AH-7921 identified in illegal products. Forensic Toxicology 31 (2):223–40. doi:10.1007/s11419-013-0182-9.
   Web of Science ®Google Scholar
• Vardakou, I., C. Pistos, and C. Spiliopoulou. 2010. Spice drugs as a new trend: Mode of action, identification and legislation. Toxicology Letters 197 (3):157–62. doi:10.1016/j.toxlet.2010.06.002.
   PubMed Web of Science ®Google Scholar