Synthetic cannabinoids: crisis of the decade
___
- 1.Drummer O, Odell M. The Forensic Pharmacology Of Drugs Of Abuse. London: Arnold, 2001.
- 2.Gaoni Y, Mechoulam R. Isolation, structure and partial synthesis of an active constituent of hashish. J Am Chem Soc 1964; 86:1646-1647.
- 3.Howlett AC, Barth F, Bonner TI, Cabral G, Casellas P, Devane WA, Felder CC, Herkenham M, Mackie K, Martin BR, Mechoulam R, Pertwee RG. International union of pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol Rev 2002; 54: 161-202.
- 4.UNODC, World Drug Report 2011. United Nation Office on drugs and crime. United Nation Publications, 2011, 175-193.
- 5.Davidson C. New psychoactive substances. Prog neuropsychopharmacol biol psychiatry 2012; 39:219-220.
- 6.Huffman JW, Dai D, Martin BR, Compton DR. Design, synthesis and pharmacology of cannabimimetic indoles. Bioorg Med Chem Lett 1994; 4:563-566.
- 7.Hoyte CO, Jacob J, Monte AA, Al-Jumaan M, Bronstein AC, Heard KJ. A characterization of synthetic cannabinoid exposures reported to the National Poison Data System in 2010. Ann Emerg Med 2012; 60:435-438.
- 8.EMCDDAEuropol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA.http://www.emcdda.europa. eu/attachements.cfm/att_155113_EN_EMCDDA-Europol%20 Annual%20Report%202011_2012_final.pdf. Accessed Feburary 21, 2013.
- 9.Vardakou I, Pistos C, Spiliopoulou Ch. Spice drugs as a new trend: Mode of action, identification and legislation. Toxicol Lett 2010; 197:157-162.
- 10.Auwärter V, Dresen S, Weinmann W, Mueller M, Puetz M, Ferreiros N. Spice and other herbal blends: Harmless incense or cannabinoid designer drugs? J Mass Spectrom 2009; 44:832-837.
- 11.Merola G, Aturkib Z, DOraziob G, Gottardoc R, Macchiaa T, Tagliaroc F, Fanalib S. Analysis of synthetic cannabinoids in herbal blends by means of nano-liquid hromatography. J Pharm Biomed Anal 2012; 71:45-53.
- 12.de Jager AD, Warner JV, Henman M, Ferguson W, Hall. LC-MS/MS method for the quantitation of metabolites of eight commonly-used synthetic cannabinoids in human urine--an Australian perspective. J Chromatogr B Analyt Technol Biomed Life Sci 2012; 897:22-31.
- 13.Grigoryev A, Savchuk S, Melnik A, Moskaleva N, Dzhurko J, Ershov M, Nosyrev A, Vedenin A, Izotov B, Zabirova I, Rozhanets V. Chromatographymass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures. J Chromatogr B Analyt Technol Biomed Life Sci 2011; 879:1126- 1136.
- 14.Uchiyama N, Kikura-Hanajiri R, Ogata J, Goda Y. Chemical analysis of synthetic cannabinoids as designer drugs in herbal products. Forensic Sci Int 2010; 198:31-38.
- 15.EMCDDA-Europol 2008 Annual Report on the Implementation of Council Decision 2005/387/JHA. Annex 2: New psychoactive substances reported to the EMCDDA and Europol for the first time in 2008 under the terms of Council Decision, 005/387/JHA. http://www.emcdda.europa.eu/attachements.cfm/att_77263_ EN_EMCDDA-Europol_Annual_Report_Art10_2008.pdf. Accessed Feburary 21, 2013.
- 16.EMCDDA, 2009 Annual report on the state of the drugs problem in Europe. European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 2009. http://www.emcdda.europa.eu/ attachements.cfm/att_93236_EN_EMCDDA_AR2009_EN.pdf. Accessed February 19, 2013.
- 17.EMCDDA, 2010 Annual report on the state of the drugs problem in Europe. European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 2010. http://www.emcdda.europa.eu/ attachements.cfm/att_120104_EN_EMCDDA_AR2010_EN.pdf. Accessed February 19, 2013.
- 18.Moosmann B, Kneisel S, Girreser U, Brecht V, Westphal F, Auwärter V. 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 2012; 220:17-22.
- 19.Moosmann B, Kneisel S, Girreser U, Brecht V, Westphal F, Auwärter V. Withdrawal phenomena and dependence syndrome after the consumption of spice gold. Dtsch Arztebl Int 2009; 106:464-467.
- 20.Fattore L, Fratta W. Beyond THC: The new generation of cannabinoid designer drugs. Front Behav Neurosci 2011; 5:60-66.
- 21.AAPCC Issues Statement on the Synthetic Drug Abuse Prevention Act. American Association of Poison Control Centre, 2012. http:// www.aapcc.org/press/2/. Accessed February 21, 2013.
- 22.Johnston, LD, OMalley PM, Bachman JG, Schulenberg JE. The rise in teen marijuana use stalls, synthetic marijuana use levels, and use of bath salts is very low. University of Michigan News Service: Ann Arbor, MI, 2012. htttp://www.monitoringthefuture. org/pressreleases/12drugpr.pdf. Accessed Feburary 21, 2013.
- 23.Hu X, Primack BA, Barnett TE, Cook RL. College students and the use of K2: An emerging drug of abuse in young persons. Subst Abuse Treat Prev Policy 2011; 6:16.
- 24.Castellanos D, Singh S, Thornton G, Avila M, Moreno A. Synthetic cannabinoid use: A case series of adolescents. J Adolesc Health 2011; 49:347-349.
- 25.Pertwee RG. Pharmacology of cannabinoid receptor ligands. Curr Med Chem 1999; 6:635-664.
- 26.Ameri A. The effects of cannabinoids on the brain. Prog Neurobiol 1999; 58:315-348.
- 27.Hájos N, Freund TF. Distinct cannabinoid sensitive receptors regulate hippocampal excitation and inhibition. Chem Phys Lipids 2002; 121:73-82.
- 28.McCarberg BH, Barkin RL. The future of cannabinoids as analgesic agents: A pharmacologic, pharmacokinetic, and pharmacodynamic overview. Am J Ther 2007; 14:475-483.
- 29.Ashton JC, Wright JL, McPartland JM, Tyndall JDA. Cannabinoid CB1 and CB2 receptor ligand specificity and the development of CB2-selective agonists. Curr Med Chem 2008; 15:1428-1443.
- 30.Wintermeyer A, Möller I, Thevis M, et al. In vitro phase I metabolism of the synthetic cannabimimetic JWH-018. Anal Bioanal Chem 2010; 398:2141-2153.
- 31.Rieder SA, Chauhan A, Singh U, Nagarkatti M, Nagarkatti P. Cannabinoid-induced apoptosis in immune cells as a pathway to immunosuppression. Immunobiology 2010; 215:598-605.
- 32.Qamri Z, Preet A, Nasser MW, Bass CE, Leone G, Barsky SH, Ganju RK. Synthetic cannabinoid receptor agonists inhibit tumor growth and metastasis of breast cancer. Mol Cancer Ther 2009; 8:3117-3129.
- 33.Olea-Herrero N, Vara D, Malagarie-Cazenave S, Díaz-Laviada I. Inhibition of human tumour prostate PC-3 cell growth by cannabinoids R(+)-methanandamide and JWH-015: Involvement of CB2. Br J Cancer 2009; 101:940-950.
- 34.Van Sickle MD, Duncan M, Kingsley PJ, et al. Identification and functional characterization of brainstem cannabinoid CB2 receptors. Science 2005; 310:329-332.
- 35.Hojo M, Sudo Y, Ando Y, Minami K, Takada M, Matsubara T, Kanaide M, Taniyama K, Sumikawa K, Uezono Y. mu-Opioid receptor forms a functional heterodimer with cannabinoid CB1 receptor: Electrophysiological and FRET assay analysis. J Pharmacol Sci 2008; 108:308-319.
- 36.Desroches J, Beaulieu P. Opioids and cannabinoids interactions: Involvement in pain management. Curr Drug Targets 2010; 11:462-473.
- 37.Aung MM, Griffin G, Huffman JW, Wu M-J, Keel C, Yang B, Showalter VM, Abood ME, Martin BR. Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug Alcohol Depend 2000; 60:133-140.
- 38.Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR. 1-Pentyl-3- phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg Med Chem Lett 2005; 15:4110-4113.
- 39.Huffman JW, Padgett LW. Recent developments in the medicinal chemistry of cannabinomimetic indoles, pyrroles and indenes. Curr Med Chem 2005; 12:1395-1411.
- 40.Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, Reggio PH, Wiley JL, Martin BR. 3-Indolyl-1-naphthylmethanes: New cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor. Bioorg Med Chem 2003; 11:539-549.
- 41.Hudson S, Ramsey J, King L, Timbers S, Maynard S, Dargan PI, Wood DM. Use of high resolution accurate mass spectrometry to detect reported and previously unreported cannabinomimetics in herbal high products. J Anal Toxicol 2010; 34:252-260.
- 42.Vandrey R, Dunn KE, Fry JA, Girling ER. A survey study to characterize use of Spice products (synthetic cannabinoids). Drug Alcohol Depend 2012; 120:238-241.
- 43.UNODC, Synthetic cannabinoids in herbal products. United Nations Office on Drugs and Crime, 2011. http://www.unodc. org/documents/scientific/Synthetic_Cannabinoids.pdf. Last accessed February 19, 2013.
- 44.Gronewold A, Skopp G. A preliminary investigation on the distribution of cannabinoids in man. Forensic Sci Int 2011; 210:7- 11.
- 45.Chimalakonda KC, Bratton SM, Le VH, Yiew KH, Dineva A, Moran CL, James LP, Moran JH, Radominska-Pandya A. Conjugation of synthetic cannabinoids JWH-018 and JWH-073, metabolites by human UDP-glucuronosyltransferases. Drug Metab Dispos 2011; 39:1967-1976.
- 46.EMCDDA, Understanding the Spice phenomenon. European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 2009. http://www.emcdda.europa.eu/attachements.cfm/att_80086_ EN_Spice%20Thematic%20paper%20%E2%80%94%20 final%20version.pdf. Last accessed February 19, 2013.
- 47.Seely KA, Brents LK, Radominska-Pandya A, Endres GW, Keyes GS, Moran JH, Prather PL. A major glucuronidated metabolite of JWH-018 is a neutral antagonist at CB1 receptors. Curr Res Toxicol 2012; 4:825-827.
- 48.Brents LK, Gallus-Zawada A, Radominska-Pandya A, Vasiljevik T, Prisinzano TE, Fantegrossi WE, Moran JH, Prather PL. Monohydroxylated metabolites of the K2 synthetic cannabinoid JWH-073 retain intermediate to high cannabinoid 1 receptor (CB1R) affinity and exhibit neutral antagonist to partial agonist activity. Biochem Pharmacol 2012; 83:952-961.
- 49.Seely KA, Lapoint J, Moran JH, Fattore L. Spice drugs are more than harmless herbal blends: A review of the pharmacology and toxicology of synthetic cannabinoids. Prog Neuropsychopharmacol Biol Psychiatry 2012; 39:234-243.
- 50.Uchiyama N, Kikura-Hanajiri R, Goda Y. Identification of a novel cannabimimetic phenylacetylindole, cannabipiperidiethanone, as a designer drug in a herbal product and its affinity for cannabinoid CB1 and CB2 receptors. Chem Pharm Bull 2011; 59:1203-1205.
- 51.Ghosh S, Preet A, Groopman JE, Ganju RK. Cannabinoid receptor CB2 modulates the CXCL12/CXCR4-mediated chemotaxis of T lymphocytes. Mol Immunol 2006; 43:2169-2179.
- 52.Lombard C, Nagarkatti M, Nagarkatti P. CB2 cannabinoid receptor agonist, JWH-015, triggers apoptosis in immune cells: Potential role for CB2-selective ligands as immunosuppressive agents. Clin Immunol 2007; 122:259-270.
- 53.Onaivi ES, Ishiguro H, Gong JP, Patel S, Perchuk A, Meozzi PA, et al. Discovery of the presence and functional expression of cannabinoid CB2 receptors in brain. Ann N Y Acad Sci 2006; 1074:514-536.
- 54.Fernández-Ruiz J, Romero J, Velasco G, Tolón RM, Ramos JA, Guzmán M. Cannabinoid CB2 receptor: A new target for controlling neural cell survival? Trends Pharmacol Sci 2007; 28:39-45.
- 55.Onaivi ES, Ishiguro H, Gong JP, Patel S, Meozzi PA, Myers L, Perchuk A, Mora Z, Tagliaferro PA, Gardner E, Brusco A, Akinshola BE, Hope B, Lujilde J, Inada T, Iwasaki S, Macharia D, Teasenfitz L, Arinami T, Uhl GR. Brain neuronal CB2 cannabinoid receptors in drug abuse and depression: From mice to human subjects. PLoS One 2008; 3:1640.
- 56.Onaivi ES, Ishiguro H, Gong JP, Patel S, Meozzi PA, Myers L, Perchuk A, Mora Z, Tagliaferro PA, Gardner E, Brusco A, Akinshola BE, Liu QR, Chirwa SS, Hope B, Lujilde J, Inada T, Iwasaki S, Macharia D, Teasenfitz L, Arinami T, Uhl GR. Functional expression of brain neuronal CB2 cannabinoid receptors are involved in the effects of drugs of abuse and in depression. Ann N Y Acad Sci 2008; 1139:434-449.
- 57.Xi ZX, Peng XQ, Li X, Song R, Zhang HY, Liu QR, Yang HJ, Bi GH, Li J, Gardner EL. Brain cannabinoid CB2 receptors modulate cocaines actions in mice. Nat Neurosci 2011; 14:1160-1166.
- 58.Di Marzo V, De Petrocellis L, Fezza F, Ligresti A, Bisogno T. Anandamide receptors. Prostaglandins Leukot Essent Fatty Acids 2002; 66:377-391.
- 59.Hudson BD, Hébert TE, Kelly ME. Ligand- and heterodimer- directed signaling of the CB(1) cannabinoid receptor. Mol Pharmacol 2010; 77:1-9.
- 60.Milligan G, Smith NJ. Allosteric modulation of heterodimeric G-protein-coupled receptors. Trends Pharmacol Sci 2007; 28:615-620.
- 61.Wood DM, Dargan PI. Novel psychoactive substances: How to understand the acute toxicity associated with the use of these substances. Ther Drug Monit 2012; 34:363-367.
- 62.Zuba D, Byrska B, Maciow M. Comparison of herbal highs composition. Anal Bioanal Chem 2011; 400:119-126.
- 63.Dresen S, Ferreirós N, Pütz M, Westphal F, Zimmermann R, Auwärter V. Monitoring of herbal mixtures potentially containing synthetic cannabinoids as psychoactive compounds. J Mass Spectrom 2010; 45:1186-1194.
- 64.Simmons J, Cookman L, Kang C, Skinner C. Three cases of Spice exposure. Clin Toxicol 2011; 49:431-433.
- 65.Simmons JR, Skinner CG, Williams J, Kang CS, Schwartz MD, Wills BK. Intoxication from smoking Spice. Ann Emerg Med 2011; 57:187-188.
- 66.Müller H, Sperling W, Köhrmann M, Huttner HB, Kornhuber J, Maler JM. The synthetic cannabinoid Spice as a trigger for an acute exacerbation of cannabis induced recurrent psychotic episodes. Schizophr Res 2010; 118:309-310.
- 67.Every-Palmer S. Warning: Legal synthetic cannabinoid-receptor agonists such as JWH018 may precipitate psychosis in vulnerable individuals. Addiction 2010; 105:1859-1860.
- 68.Schneir AB, Cullen J, Ly BT. Spice girls: Synthetic cannabinoid intoxication. J Emerg Med 2011; 40:296-299.
- 69.Teske J, Weller JP, Fieguth A, Rothämel T, Schulz Y, Tröger HD. Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl) methanone (JWH- 018) in human serum by liquid chromatographytandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 2010; 878:2659-2663.
- 70.Harris CR, Brown A. Synthetic cannabinoid intoxication: A case series and review. J Emerg Med 2013; 44:360-366.
- 71.Reece AS. Chronic toxicology of cannabis. Clin Toxicol 2009; 47:517-524.
- 72.Jerry J, Collins G, Streem D. Synthetic legal intoxicating drugs: The emerging incense and bath salt phenomenon. Cleve Clin J Med 2012; 79:258-264.
- 73.Mir A, Obafemi A, Young A, Kane C. Myocardial infarction associated with use of the synthetic cannabinoid K2. Pediatrics 2011; 128:1622-1627.
- 74.Rosenbaum CD, Carreiro SP, Babu KM. Here today, gone tomorrow and back again? A review of herbal marijuana alternatives (K2, Spice), synthetic cathinones bath salts), Kratom, Salvia divinorum, methoxetamine, and piperazines. J Med Toxicol 2012; 8:15-32.
- 75.McGrath J, Welham J, Scott J, Varghese D, Degenhardt L, Hayatbakhsh MR, Alati R, Williams GM, Bor W, Najman JM. Association between cannabis use and psychosis-related outcomes using sibling pair analysis in a cohort of young adults. Arch Gen Psychiatry 2010; 67:440-447.
- 76.Arseneault L, Cannon M, Poulton R, Murray R, Caspi A, Moffitt TE. Cannabis use in adolescence and risk for adult psychosis: Longitudinal prospective study. BMJ 2002; 325:1212-1213.
- 77.DSouza DC, Sewell RA, Ranganathan M. Cannabis and psychosis/schizophrenia: Human studies. Eur Arch Psychiatry Clin Neurosci 2009; 259:413-431.
- 78.Every-Palmer S. Synthetic cannabinoid JWH-018 and psychosis: An explorative study. Drug Alcohol Depend 2011; 117:152-157.
- 79.Hurst D, Loeffler G, McLay R. Psychosis associated with synthetic cannabinoid agonists: A case series. Am J Psychiatry 2011; 168:1119.
- 80.Lin CY, Wheelock AM, Morin D, Baldwin RM, Lee MG, Taff A, Plopper C, Buckpitt A, Rohde A. Toxicity and metabolism of methylnaphthalenes: Comparison with naphthalene and 1-nitronaphthalene. Toxicology 2009; 260:16-27.
- 81.Gregori A, Damiano F, Bonavia M, Mileo V, Varani F, Monfreda M. Identification of two cannabimimetic compounds WIN48098 and AM679 in illegal products. Science and Justice 2012 (inpress).
- 82.Dresen S, Kneisel S, Weinmann W, Zimmermann R, Auwärter V. Development and validation of a liquid chromatography-tandem mass spectrometry method for the quantitation of synthetic cannabinoids of the aminoalkylindole type and methanandamide in serum and its application to forensic samples. J Mass Spectrom 2011; 46:163-171.
- 83.Coulter C, Garnier M, Moore C. Synthetic cannabinoids in oral fluid. J Anal Toxicol 2011; 35:424-430.
- 84.Hutter M, Broecker S, Kneise Sl, Auwärter V. Identification of the major urinary metabolites in man of seven synthetic cannabinoids of the aminoalkylindole type present as adulterants in herbal mixtures using LC-MS/MS techniques. J Mass Spectrom 2012; 47:54-65.
- 85.Hutter M, Kneisel S, Auwärter V, Neukamm MA. Determination of 22 synthetic cannabinoids in human hair by liquid chromatographytandem mass spectrometry. Journal of Chromatography B Analyt Technol Biomed Life Sci 2012; 903:95-101.
- 86.Möller I, Wintermeyer A, Bender K, et al. Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls. Drug Test Anal 2011; 3:609-620.
- 87.2011 National report (2010 data) to the EMCDDA. TURKEY New Development, Trends and in-depth information on selected issues. Reitox National Focal Point, 2012. http://www.emcdda. europa.eu/attachements.cfm/att_191577_EN_Turkey_2011.pdf. Last accessed Feburary 18, 2013.
- 88.Griffiths P, Sedefov R, Gallegos A, Lopez D. How globalization and market innovation challenge how we think about and respond to drug use: Spice a case study. Addiction 2010; 105:951-953.
- 89.Brents LK, Reichard EE, Zimmerman SM, Moran JH, Fantegrossi WE, Prather PL. Phase I hydroxylated metabolites of the K2 synthetic cannabinoid JWH-018 retain in vitro and in vivo cannabinoid 1 receptor affinity and activity. PLoS One 2011; 6:e21917.