1,792
Views
55
CrossRef citations to date
0
Altmetric
Review

Synthetic cannabinoid receptor agonists: classification and nomenclature

, , &
Pages 82-98 | Received 24 Feb 2019, Accepted 23 Aug 2019, Published online: 16 Sep 2019

References

  • Waugh J, Najafi J, Hawkins L, et al. Epidemiology and clinical features of toxicity following recreational use of synthetic cannabinoid receptor agonists: a report from the United Kingdom National Poisons Information Service. Clin Toxicol. 2016;54(6):512–518.
  • Weinstein AM, Rosca P, Fattore L, et al. Synthetic cathinone and cannabinoid designer drugs pose a major risk for public health. Front Psychiatry. 2017;8:1–11.
  • Iversen L, Gibbons S. ‘Third generation’ synthetic cannabinoids [Internet]. 2014. [cited 2019 Apr 26]. Available from: https://www.gov.uk/government/publications/third-generation-synthetic-cannabinoids.
  • Fantegrossi WE, Moran JH, Radominska-Pandya A, et al. Distinct pharmacology and metabolism of K2 synthetic cannabinoids compared to Δ(9)-THC: mechanism underlying greater toxicity? Life Sci. 2014;97(1):45–54.
  • Tai S, Fantegrossi WE. Pharmacological and toxicological effects of synthetic cannabinoids and their metabolites. In: Baumann MH, Glennon RA, Wiley JL, editors. Neuropharmacology of new psychoactive substances. The science behind the headlines. Cham (Switzerland): Springer International Publishing; 2017. p. 249–262.
  • Ligresti A, De Petrocellis L, Di Marzo V. From phytocannabinoids to cannabinoid receptors and endocannabinoids: pleiotropic physiological and pathological roles through complex pharmacology. Physiol Rev. 2016;96(4):1593–1659.
  • Atwood BK, Lee D, Straiker A, et al. CP47,497-C8 and JWH073, commonly found in “‘Spice’ herbal blends, are potent and efficacious CB(1) cannabinoid receptor agonists”. Eur J Pharmacol. 2011;659(2–3):139–145.
  • Wiley JL, Lefever TW, Marusich JA, et al. Evaluation of first generation synthetic cannabinoids on binding at non-cannabinoid receptors and in a battery of in vivo assays in mice. Neuropharmacology. 2016;110:143–153.
  • Wiley J, Marusich J, Huffman J, et al. Hijacking of basic research: the case of synthetic cannabinoids. Methods Rep RTI Press. 2013;17971. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3567606/
  • Shevyrin V, Melkozerov V, Endres G, et al. On a new cannabinoid classification system: a sight on the illegal market of novel psychoactive substances. Cannabis Cannabinoid Res. 2016;1(1):186–194.
  • Paulke A, Proschak E, Sommer K, et al. Synthetic cannabinoids: in silico prediction of the cannabinoid receptor 1 affinity by a quantitative structure-activity relationship model. Toxicol Lett. 2016;245:1–6.
  • EMCDDA. European Database on New Drugs (EDND) [Internet]. [cited 2019 Apr 26]. Available from: https://ednd2.emcdda.europa.eu/ednd/login.
  • Tait RJ, Caldicott D, Mountain D, et al. A systematic review of adverse events arising from the use of synthetic cannabinoids and their associated treatment. Clin Toxicol. 2016;54(1):1–13.
  • Hill SL, Najafi J, Dunn M, et al. 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. Clin Toxicol. 2016;54(8):638–643.
  • Hermanns-Clausen M, Müller D, Kithinji J, et al. Acute side effects after consumption of the new synthetic cannabinoids AB-CHMINACA and MDMB-CHMICA. Clin Toxicol. 2018;56(6):404–411.
  • Hill SL, Dargan PI. Patterns of acute toxicity associated with new psychoactive substances. Handb Exp Pharmacol. 2018;252:475–494.
  • EMCDDA. EMCDDA–Europol 2010 Annual report on the implementation of Council Decision 2005/387/JHA [Internet]. 2010. [cited 2019 Apr 26]. Available from: http://www.emcdda.europa.eu/publications-seriestype/implementation-reports_en.
  • EMCDDA. EMCDDA–Europol 2011 Annual report on the implementation of Council Decision 2005/387/JHA [Internet]. 2011. [cited 2019 Apr 26]. Available from: http://www.emcdda.europa.eu/publications-seriestype/implementation-reports_en.
  • EMCDDA. EMCDDA–Europol 2012 Annual report on the implementation of Council Decision 2005/387/JHA [Internet]. 2012. [cited 2019 Apr 26]. Available from: http://www.emcdda.europa.eu/publications-seriestype/implementation-reports_en.
  • EMCDDA. EMCDDA–Europol 2013 Annual report on the implementation of Council Decision 2005/387/JHA [Internet]. 2013. [cited 2019 Apr 26]. Available from: http://www.emcdda.europa.eu/publications-seriestype/implementation-reports_en.
  • EMCDDA. EMCDDA–Europol 2014 Annual report on the implementation of Council Decision 2005/387/JHA [Internet]. 2014. [cited 2019 Apr 26]. Available from: http://www.emcdda.europa.eu/publications-seriestype/implementation-reports_en.
  • EMCDDA. EMCDDA–Europol 2015 Annual report on the implementation of Council Decision 2005/387/JHA [Internet]. 2015. [cited 2019 Apr 26]. Available from: http://www.emcdda.europa.eu/publications-seriestype/implementation-reports_en.
  • EMCDDA. EMCDDA–Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA [Internet]. 2016. [cited 2019 Apr 26]. Available from: http://www.emcdda.europa.eu/publications-seriestype/implementation-reports_en.
  • EMCDDA. EMCDDA–Europol 2017 Annual report on the implementation of Council Decision 2005/387/JHA [Internet]. 2017. [cited 2019 Apr 26]. Available from: http://www.emcdda.europa.eu/publications-seriestype/implementation-reports_en.
  • EMCDDA. Perspectives on drugs: Synthetic cannabinoids in Europe [Internet]. 2017. [cited 2019 Apr 26]. Available from: http://www.emcdda.europa.eu/topics/pods/synthetic-cannabinoids_en.
  • Daniela A, Ar D. 36th International Congress of the European Association of Poisons Centres and Clinical Toxicologists (EAPCCT) 24-27 May, 2016, Madrid, Spain. Clin. Toxicol. 2016;54:344–519.
  • Helander A, Beck O, Hägerkvist R, et al. Identification of novel psychoactive drug use in Sweden based on laboratory analysis-initial experiences from the STRIDA project. Scand. J. Clin. Lab. Invest. 2013;73(5):400–406.
  • WHO. Critical review report: ADB-FUBINACA [Internet]. 2018. [cited 2019 Apr 26]. Available from: https://www.who.int/medicines/access/controlled-substances/ADB_Fubinaca.pdf.
  • UNODC. Recommended methods for the identification and analysis of synthetic cannabinoid receptor agonists in seized materials [Internet]. 2013. [cited 2019 Apr 26]. Available from: https://www.unodc.org/documents/scientific/ST-NAR-40-Ebook_1.pdf.
  • Debruyne D, Le Boisselier R. Emerging drugs of abuse: current perspectives on synthetic cannabinoids. Subst Abuse Rehabil. 2015;113:113–129.
  • Hess C, Schoeder CT, Pillaiyar T, et al. Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice. Forensic Toxicol. 2016;34(2):329–343.
  • Schoeder CT, Hess C, Madea B, et al. Pharmacological evaluation of new constituents of “Spice”: synthetic cannabinoids based on indole, indazole, benzimidazole and carbazole scaffolds. Forensic Toxicol. 2018;36(2):385–403.
  • Angerer V, Bisel P, Moosmann B, et al. Separation and structural characterization of the new synthetic cannabinoid JWH-018 cyclohexyl methyl derivative “NE-CHMIMO” using flash chromatography, GC-MS, IR and NMR spectroscopy. Forensic Sci Int. 2016;266:e93–e98.
  • Hill SL, Dunn M, Cano C, et al. Human toxicity caused by indole and indazole carboxylate synthetic cannabinoid receptor agonists: from horizon scanning to notification. Clin Chem. 2018;64(2):346–354.
  • Uchiyama N, Kawamura M, Kikura-Hanajiri R, et al. Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1- pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole- 3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB. Forensic Toxicol. 2012;30:114–125.
  • Shevyrin V, Melkozerov V, Nevero A, et al. Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group. Anal Bioanal Chem. 2015;407(21):6301–6315.
  • Aung MM, Griffin G, Huffman JW, et al. Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug Alcohol Depend. 2000;60(2):133–140.
  • Wiley J, Compton D, Dai D, et al. Structure-activity relationships of indole- and pyrrole-derived cannabinoids. J Pharmacol Exp Ther. 1998;285(3):995–1004.
  • Wiley JL, Marusich JA, Huffman JW. Moving around the molecule: relationship between chemical structure and in vivo activity of synthetic cannabinoids. Life Sci. 2014;97(1):55–63.
  • Uchiyama N, Kawamura M, Kikura-Hanajiri R, et al. Identification and quantitation of two cannabimimetic 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. 2011;29(1):25–37.
  • Poklis J, Amira D, Wise L, et al. Detection and disposition of JWH-018 and JWH-073 in mice after exposure to “Magic Gold” smoke. Forensic Sci Int. 2012;220(1–3):91–96.
  • Logan BK, Reinhold LE, Xu A, et al. Identification of synthetic cannabinoids in herbal incense blends in the United States. J Forensic Sci. 2012;57(5):1168–1180.
  • Banister SD, Stuart J, Kevin RC, et al. 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. ACS Chem. Neurosci. 2015;6(8):1445–1458.
  • Banister SD, Moir M, Stuart J, et al. Pharmacology of indole and indazole synthetic cannabinoid designer drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA. ACS Chem Neurosci. 2015;6(9):1546–1559.
  • Banister SD, Longworth M, Kevin R, et al. Pharmacology of valinate and tert-leucinate synthetic cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and their analogues. ACS Chem Neurosci. 2016;7(9):1241–1254.
  • Yeter O. Identification of the synthetic cannabinoid 1-(4-cyanobutyl)-N-(2-phenylpropan-2-yl)-1H- indazole-3-carboxamide (CUMYL-4CN-BINACA) in plant material and quantification in post-mortem blood samples. J Anal Toxicol. 2017;41(9):720–728.
  • Liu C, Jia W, Hua Z, et al. Identification and analytical characterization of six synthetic cannabinoids NNL‐3, 5F–NPB‐22‐7N, 5F–AKB‐48‐7N, 5F–EDMB‐PINACA, EMB‐FUBINACA, and EG‐018. Drug Test Anal. 2017;9(8):1251–1261.
  • Adamowicz P. Fatal intoxication with synthetic cannabinoid MDMB-CHMICA. Forensic Sci Int. 2016;261:e5–e10.
  • Angerer V, Franz F, Schwarze B, et al. Reply to “sudden cardiac death following use of the synthetic cannabinoid MDMB-CHMICA”. J Anal Toxicol.. 2016;40(3):240–242.
  • Bäckberg M, Tworek L, Beck O, et al. Analytically confirmed intoxications involving MDMB-CHMICA from the STRIDA project. J Med Toxicol. 2017;13(1):52–60.
  • WEDINOS. Hospitalisation from synthetic cannabinoid MMB- CHMINACA [Internet]. 2015. [cited 2019 Apr 26]. Available from: http://asfa.cymru/wp-content/uploads/2015/07/MMB-CHMINACA-MDMB-CHMICA-alert.pdf.
  • Uchiyama N, Matsuda S, Kawamura M, et al. 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-79. Forensic Toxicol. 2013;31:223–240.
  • Tang ASY, Loh SWX, Koh HB, et al. Differentiation and identification of 5F-PB-22 and its isomers. Forensic Sci Int. 2017;279:53–59.
  • Huffman JW, Szklennik PV, Almond A, et al. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg Med Chem Lett. 2005;15(18):4110–4113.
  • Weber C, Pusch S, Schollmeyer D, et al. Characterization of the synthetic cannabinoid MDMB-CHMCZCA. Beilstein J Org Chem. 2016;12:2808–2815.
  • Mogler L, Franz F, Wilde M, et al. Phase I metabolism of the carbazole‐derived synthetic cannabinoids EG‐018, EG‐2201, and MDMB‐CHMCZCA and detection in human urine samples. Drug Test Anal. 2018;10(9):1417–1429.
  • Angerer V, Mogler L, Steitz J, et al. Structural characterization and pharmacological evaluation of the new synthetic cannabinoid CUMYL‐PEGACLONE. Drug Test Anal. 2018;10(3):597–603.
  • Mogler L, Halter S, Wilde M, et al. Human phase I metabolism of the novel synthetic cannabinoid 5F - CUMYL - PEGACLONE. Forensic Toxicol. 2019;37(1):154–163.
  • Mogler L, Wilde M, Huppertz LM, et al. Phase I metabolism of the recently emerged synthetic cannabinoid CUMYL‐PEGACLONE and detection in human urine samples. Drug Test Anal. 2018;10(5):886–891.
  • EMCDDA. EMCDDA–Europol 2017 Annual Report on the implementation of Council Decision 2005/387/JHA. 2017.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.