Spice drugs are more than harmless herbal blends: A review of the pharmacology and toxicology of synthetic cannabinoids
Tài liệu tham khảo
Akirav, 2011, The role of cannabinoids in modulating emotional and non-emotional memory processes in the hippocampus, Front Behav Neurosci, 5, 34, 10.3389/fnbeh.2011.00034
Ameri, 1999, The effects of cannabinoids on the brain, Prog Neurobiol, 58, 315, 10.1016/S0301-0082(98)00087-2
American Association of Poison Control Centre (AAPCC)
Arseneault, 2002, Cannabis use in adolescence and risk for adult psychosis: longitudinal prospective study, BMJ, 325, 1212, 10.1136/bmj.325.7374.1212
Ashton, 2011, Endocannabinoid system dysfunction in mood and related disorders, Acta Psychiatr Scand, 124, 250, 10.1111/j.1600-0447.2011.01687.x
Atwood, 2010, JWH018, a common constituent of ‘Spice’ herbal blends, is a potent and efficacious cannabinoid CB1 receptor agonist, Br J Pharmacol, 160, 133, 10.1111/j.1476-5381.2009.00582.x
Auwärter, 2009, ‘Spice’ and other herbal blends: harmless incense or cannabinoid designer drugs?, J Mass Spectrom, 2009, 832, 10.1002/jms.1558
Balster, 1992, Delta 9-tetrahydrocannabinol discrimination in rats as a model for cannabis intoxication, Neurosci Biobehav Rev, 16, 55, 10.1016/S0149-7634(05)80051-X
Barrett, 1995, Pharmacological specificity of delta 9-tetrahydrocannabinol discrimination in rats, Psychopharmacology, 118, 419, 10.1007/BF02245942
Brents, 2011, 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, 6, e21917, 10.1371/journal.pone.0021917
Brents, 2012, 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, 83, 952, 10.1016/j.bcp.2012.01.004
Brown, 2011, New Zealand bans synthetic cannabinoids, BMJ, 343, d5395, 10.1136/bmj.d5395
Bryner, J., 2010. Fake weed, real drug: K2 causing hallucinations in teens. Live Science. March 3, 2010. http://www.livescience.com/health/fake-marijuana-k2-hallucinations-100303.html (accessed Mar 16, 2010).
Carroll, 2012, Designer drugs: a medicinal chemistry perspective, Ann N Y Acad Sci, 1248, 18, 10.1111/j.1749-6632.2011.06199.x
Castellanos, 2011, Synthetic cannabinoid use: a case series of adolescents, J Adolesc Health, 49, 347, 10.1016/j.jadohealth.2011.08.002
Chang, 2012, Homology modelling of cannabinoid receptors: discovery of cannabinoid analogues for therapeutic use, Methods Mol Biol, 819, 595, 10.1007/978-1-61779-465-0_35
Chimalakonda, 2011, Conjugation of synthetic cannabinoids JWH-018 and JWH-073, metabolites by human UDP-glucuronosyltransferases, Drug Metab Dispos, 39, 1967, 10.1124/dmd.111.040709
Chimalakonda, 2011, Solid-phase extraction and quantitative measurement of omega and omega-1 metabolites of JWH-018 and JWH-073 in human urine, Anal Chem, 83, 6381, 10.1021/ac201377m
Coulter, 2011, Synthetic cannabinoids in oral fluid, J Anal Toxicol, 35, 424, 10.1093/anatox/35.7.424
D'Ambra, 1992, Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor, J Med Chem, 35, 124, 10.1021/jm00079a016
Desroches, 2010, Opioids and cannabinoids interactions: involvement in pain management, Curr Drug Targets, 11, 462, 10.2174/138945010790980303
Di Marzo, 2006, Plant, synthetic, and endogenous cannabinoids in medicine, Annu Rev Med, 57, 553, 10.1146/annurev.med.57.011205.135648
Di Marzo, 2002, Anandamide receptors. Prostaglandins Leukot. Essent, Fatty Acids, 66, 377, 10.1054/plef.2001.0349
Dresen, 2010, Monitoring of herbal mixtures potentially containing synthetic cannabinoids as psychoactive compounds, J Mass Spectrom, 45, 1095, 10.1002/jms.1811
Dresen, 2011, 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, 46, 163, 10.1002/jms.1877
Drug Enforcement Administration (DEA), 2011, Schedules of controlled substances: temporary placement of five synthetic cannabinoids into schedule I, Fed Regist, 76
D'Souza, 2009, Cannabis and psychosis/schizophrenia: human studies, Eur Arch Psychiatry Clin Neurosci, 259, 413, 10.1007/s00406-009-0024-2
Eissenstat, 1995, Aminoalkylindoles: structure–activity relationships of novel cannabinoid mimetics, J Med Chem, 38, 3094, 10.1021/jm00016a013
ElSohly, 2011, Liquid chromatography-tandem mass spectrometry analysis of urine specimens for K2 (JWH-018) metabolites, J Anal Toxicol, 35, 487, 10.1093/anatox/35.7.487
Engeli, 2012, Central and peripheral cannabinoid receptors as therapeutic targets in the control of food intake and body weight, Handb Exp Pharmacol, 209, 357, 10.1007/978-3-642-24716-3_17
European Monitoring Centre for Drugs, Drug Addiction (EMCDDA), 2009
Every-Palmer, 2010, Warning: legal synthetic cannabinoid-receptor agonists such as JWH018 may precipitate psychosis in vulnerable individuals, Addiction, 105, 1859, 10.1111/j.1360-0443.2010.03119.x
Every-Palmer, 2011, Synthetic cannabinoid JWH-018 and psychosis: an explorative study, Drug Alcohol Depend, 117, 152, 10.1016/j.drugalcdep.2011.01.012
Fattore, 2011, Beyond THC: the new generation of cannabinoid designer drugs, Front Behav Neurosci, 5, 60, 10.3389/fnbeh.2011.00060
Fernández-Ruiz, 2007, Cannabinoid CB2 receptor: a new target for controlling neural cell survival?, Trends Pharmacol Sci, 28, 39, 10.1016/j.tips.2006.11.001
Ferraro, 2001, Cannabinoid receptor agonist WIN 55,212-2 inhibits rat cortical dialysate gamma-aminobutyric acid levels, J Neurosci Res, 66, 298, 10.1002/jnr.1224
Ferraro, 2001, The cannabinoid receptor agonist WIN 55,212-2 regulates glutamate transmission in rat cerebral cortex: an in vivo and in vitro study, Cereb Cortex, 11, 728, 10.1093/cercor/11.8.728
Fišar, 2010, Inhibition of monoamine oxidase activity by cannabinoids. Naunyn Schmiedebergs, Arch Pharmacol, 381, 563, 10.1007/s00210-010-0517-6
Fišar, 2012, Cannabinoids and monoamine neurotransmission with focus on monoamine oxidase, Prog Neuropsychopharmacol Biol Psychiatry, 10.1016/j.pnpbp.2011.12.010
Forrester, 2011, Synthetic cannabinoid exposures reported to Texas poison centers, J Addict Dis, 30, 351, 10.1080/10550887.2011.609807
Gerra, 2010, Pharmacology and toxicology of Cannabis derivatives and endocannabinoid agonists, Recent Pat CNS Drug Discov, 5, 46, 10.2174/157488910789753521
Ghosh, 2006, Cannabinoid receptor CB2 modulates the CXCL12/CXCR4-mediated chemotaxis of T lymphocytes, Mol Immunol, 43, 2169, 10.1016/j.molimm.2006.01.005
Ginsburg, 2012, JWH-018 and JWH-073: Δ9-tetrahydrocannabinol-like discriminative stimulus effects in monkeys, J Pharmacol Exp Ther, 340, 37, 10.1124/jpet.111.187757
Gottardo, 2012, Direct screening of herbal blends for new synthetic cannabinoids by MALDI-TOF MS, J Mass Spectrom, 47, 141, 10.1002/jms.2036
Griffiths, 2010, How globalization and market innovation challenge how we think and respond to drug use: ‘Spice’ a case study, Addiction, 105, 951, 10.1111/j.1360-0443.2009.02874.x
Grigoryev, 2011, Gas and liquid chromatography-mass spectrometry studies on the metabolism of the synthetic phenylacetylindole cannabimimetic JWH-250, the psychoactive component of smoking mixtures, J Chromatogr B Analyt Technol Biomed Life Sci, 879, 2519, 10.1016/j.jchromb.2011.07.004
Grigoryev, 2011, Chromatography-mass 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, 879, 1126, 10.1016/j.jchromb.2011.03.034
Gronewold, 2011, A preliminary investigation on the distribution of cannabinoids in man, Forensic Sci Int, 210, e7, 10.1016/j.forsciint.2011.04.010
Hájos, 2002, Distinct cannabinoid sensitive receptors regulate hippocampal excitation and inhibition, Chem Phys Lipids, 121, 73, 10.1016/S0009-3084(02)00149-4
Hill, 2006, Altered responsiveness of serotonin receptor subtypes following long-term cannabinoid treatment, Int J Neuropsychopharmacol, 9, 277, 10.1017/S1461145705005651
Hillebrand, 2010, Legal highs on the Internet, Subst Use Misuse, 45, 330, 10.3109/10826080903443628
Ho, 1996, Determination of the cannabinoid receptors in mouse×rat hybridoma NG108-15 cells and rat GH4C1 cells, Neurosci Lett, 212, 123, 10.1016/0304-3940(96)12792-0
Hojo, 2008, mu-Opioid receptor forms a functional heterodimer with cannabinoid CB1 receptor: electrophysiological and FRET assay analysis, J Pharmacol Sci, 108, 308, 10.1254/jphs.08244FP
Hu, 2011, College students and use of K2: an emerging drug of abuse in young persons, Subst Abuse Treat Prev Policy, 6, 16, 10.1186/1747-597X-6-16
Hudson, 2011, The emergence and analysis of synthetic cannabinoids, Drug Test Anal, 3, 466, 10.1002/dta.268
Hudson, 2010, Ligand- and heterodimer-directed signaling of the CB(1) cannabinoid receptor, Mol Pharmacol, 77, 1, 10.1124/mol.109.060251
Hudson, 2010, Use of high-resolution accurate mass spectrometry to detect reported and previously unreported cannabinomimetics in ‘herbal high’ products, J Anal Toxicol, 34, 252, 10.1093/jat/34.5.252
Huffman, 2005, CB2 receptor ligands, Mini Rev Med Chem, 5, 641, 10.2174/1389557054368844
Huffman, 2009, Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions, 1, 49
Huffman, 2005, Recent developments in the medicinal chemistry of cannabinomimetic indoles, pyrroles and indenes, Curr Med Chem, 12, 1395, 10.2174/0929867054020864
Huffman, 1994, Design, synthesis and pharmacology of cannabimimetic indoles, Bioorg Med Chem Lett, 4, 563, 10.1016/S0960-894X(01)80155-4
Hurst, 2011, Psychosis associated with synthetic cannabinoid agonists: a case series, Am J Psychiatry, 168, 1119, 10.1176/appi.ajp.2011.11010176
Jack
Jankovics, 2012, Detection and identification of the new potential synthetic cannabinoids 1-pentyl-3-(2-iodobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary, Forensic Sci Int, 214, 27, 10.1016/j.forsciint.2011.07.011
Järbe, 2011, Cannabinergic aminoalkylindoles, including AM678=JWH018 found in ‘Spice’, examined using drug (Δ(9)-tetrahydrocannabinol) discrimination for rats, Behav Pharmacol, 22, 498, 10.1097/FBP.0b013e328349fbd5
Lapoint, 2011, Severe toxicity following synthetic cannabinoid ingestion, Clin Toxicol, 49, 760, 10.3109/15563650.2011.609822
Lindigkeit, 2009, Spice: a never ending story?, Forensic Sci Int, 2009, 58, 10.1016/j.forsciint.2009.06.008
Lombard, 2007, CB2 cannabinoid receptor agonist, JWH-015, triggers apoptosis in immune cells: potential role for CB2-selective ligands as immunosuppressive agents, Clin Immunol, 122, 259, 10.1016/j.clim.2006.11.002
Mackie, 2006, Cannabinoid receptors as therapeutic targets, Annu Rev Pharmacol Toxicol, 46, 101, 10.1146/annurev.pharmtox.46.120604.141254
Makriyannis, A., Deng, H., 2001. WO Patent 200128557. Cannabimimetic indole derivatives, granted 2001-06-07.
Marzouk
Matsuda, 1990, Structure of a cannabinoid receptor and functional expression of the cloned cDNA, Nature, 346, 561, 10.1038/346561a0
McGrath, 2010, Association between cannabis use and psychosis-related outcomes using sibling pair analysis in a cohort of young adults, Arch Gen Psychiatry, 67, 440, 10.1001/archgenpsychiatry.2010.6
Milligan, 2007, Allosteric modulation of heterodimeric G-protein-coupled receptors, Trends Pharmacol Sci, 28, 615, 10.1016/j.tips.2007.11.001
Mir, 2011, Myocardial infarction associated with use of the synthetic cannabinoid K2, Pediatrics, 128, 1622, 10.1542/peds.2010-3823
Möller, 2011, Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls, Drug Test Anal, 3, 609, 10.1002/dta.158
Moran, 2011, Smart resource allocation needed to study ‘legal highs’, Nat Med, 17, 1339, 10.1038/nm1111-1339
Moran, 2011, Quantitative measurement of JWH-018 and JWH-073 metabolites excreted in human urine, Anal Chem, 83, 4228, 10.1021/ac2005636
Müller, 2010, The synthetic cannabinoid Spice as a trigger for an acute exacerbation of cannabis induced recurrent psychotic episodes, Schizophr Res, 118, 309, 10.1016/j.schres.2009.12.001
Mustata, 2009, Spice drugs: cannabinoids as a new designer drugs, Adicciones, 21, 181, 10.20882/adicciones.227
Nakajima, 2011, Identification and quantitation of cannabimimetic compound JWH-250 as an adulterant in products obtained via the internet, Forensic Toxicol, 29, 51, 10.1007/s11419-010-0101-2
Nasser, 2011, Crosstalk between chemokine receptor CXCR4 and cannabinoid receptor CB2 in modulating breast cancer growth and invasion, PLoS One, 6, e23901, 10.1371/journal.pone.0023901
Olea-Herrero, 2009, Inhibition of human tumour prostate PC-3 cell growth by cannabinoids R(+)-methanandamide and JWH-015: involvement of CB2, Br J Cancer, 101, 940, 10.1038/sj.bjc.6605248
Onaivi, 2006, Discovery of the presence and functional expression of cannabinoid CB2 receptors in brain, Ann N Y Acad Sci, 1074, 514, 10.1196/annals.1369.052
Onaivi, 2008, Brain neuronal CB2 cannabinoid receptors in drug abuse and depression: from mice to human subjects, PLoS One, 3, e1640, 10.1371/journal.pone.0001640
Onaivi, 2008, 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, 1139, 434, 10.1196/annals.1432.036
Penn, 2011, Detection of synthetic cannabinoids in herbal incense products, Clin Biochem, 44, 1163, 10.1016/j.clinbiochem.2011.06.078
Pertwee, 2010, International Union of Basic and Clinical Pharmacology. LXXIX. Cannabinoid receptors and their ligands: beyond CB1 and CB2, Pharmacol Rev, 62, 588, 10.1124/pr.110.003004
Phelps, 2005, Contributions of the amygdala to emotion processing: from animal models to human behavior, Neuron, 48, 175, 10.1016/j.neuron.2005.09.025
Pistis, 2002, Delta(9)-tetrahydrocannabinol decreases extracellular GABA and increases extracellular glutamate and dopamine levels in the rat prefrontal cortex: an in vivo microdialysis study, Brain Res, 948, 155, 10.1016/S0006-8993(02)03055-X
Psychonaut Web Mapping Research Group, 2010
Qamri, 2009, Synthetic cannabinoid receptor agonists inhibit tumor growth and metastasis of breast cancer, Mol Cancer Ther, 8, 3117, 10.1158/1535-7163.MCT-09-0448
Rieder, 2010, Cannabinoid-induced apoptosis in immune cells as a pathway to immunosuppression, Immunobiology, 215, 598, 10.1016/j.imbio.2009.04.001
Schifano, 2006, Drugs on the web; the Psychonaut 2002 EU project, Prog Neuropsychopharmacol Biol Psychiatry, 30, 640, 10.1016/j.pnpbp.2005.11.035
Schneir, 2012, Convulsions associated with the use of a synthetic cannabinoid product, J Med Toxicol, 8, 62, 10.1007/s13181-011-0182-2
Schneir, 2011, “Spice” girls: synthetic cannabinoid intoxication, J Emerg Med, 40, 296, 10.1016/j.jemermed.2010.10.014
Seely, 2011, Marijuana-based drugs: innovative therapeutics or designer drugs of abuse?, Mol Interv, 11, 36, 10.1124/mi.11.1.6
Seely, 2012, A major glucuronidated metabolite of JWH-018 is a neutral antagonist at CB1 receptors, Curr Res Toxicol, 4, 825, 10.1021/tx3000472
Simmons, 2011, Three cases of “spice” exposure, Clin Toxicol, 49, 431, 10.3109/15563650.2011.584316
Simmons, 2011, Intoxication from smoking “Spice”, Ann Emerg Med, 57, 187, 10.1016/j.annemergmed.2010.08.039
Sobolevsky, 2010, Detection of JWH-018 metabolites in smoking mixture post-administration urine, Forensic Sci Int, 200, 141, 10.1016/j.forsciint.2010.04.003
Solinas, 2006, Using drug-discrimination techniques to study the abuse-related effects of psychoactive drugs in rats, Nat Protoc, 1, 1194, 10.1038/nprot.2006.167
Tamminga, 2010, The hippocampal formation in schizophrenia, Am J Psychiatry, 167, 1178, 10.1176/appi.ajp.2010.09081187
Teske, 2010, Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography–tandem mass spectrometry, J Chromatogr B Analyt Technol Biomed Life Sci, 878, 2659, 10.1016/j.jchromb.2010.03.016
Tomiyama, 2011, Cytotoxicity of synthetic cannabinoids found in “Spice” products: the role of cannabinoid receptors and the caspase cascade in the NG 108‐15 cell line, Toxicol Lett, 207, 12, 10.1016/j.toxlet.2011.08.021
Uchiyama, 2010, Chemical analysis of synthetic cannabinoids as designer drugs in herbal products, Forensic Sci Int, 198, 31, 10.1016/j.forsciint.2010.01.004
Uchiyama, 2011, Identification and quantitative analyses 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, 29, 25, 10.1007/s11419-010-0100-3
Uchiyama, 2011, 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, 59, 1203, 10.1248/cpb.59.1203
UK Statutory Instrument, 2009, No. 3209. Dangerous drugs
United Nation Office on Drugs and Crime (UNODC), 2011, 175
Vandrey, 2012, A survey study to characterize use of Spice products (synthetic cannabinoids), Drug Alcohol Depend, 120, 238, 10.1016/j.drugalcdep.2011.07.011
Vann, 2009, Discriminative stimulus properties of delta9-tetrahydrocannabinol (THC) in C57Bl/6J mice, Eur J Pharmacol, 615, 102, 10.1016/j.ejphar.2009.05.010
Vardakou, 2010, Spice drugs as a new trend: mode of action, identification and legislation, Toxicol Lett, 197, 157, 10.1016/j.toxlet.2010.06.002
Verster, 2010, The popularity of “legal highs”, Curr Drug Abuse Rev, 3, 196, 10.2174/1874473711003040196
Wells, 2011, The “new” marijuana, Ann Pharmacother, 45, 414, 10.1345/aph.1P580
Westphal, 2012, Identification of 1-butyl-3-(1-(4-methyl)naphthoyl)indole in a herbal mixture, Forensic Sci Int, 215, 8, 10.1016/j.forsciint.2011.03.031
Wiley, 1995, Discriminative stimulus effects of CP 55,940 and structurally dissimilar cannabinoids in rats, Neuropharmacology, 34, 669, 10.1016/0028-3908(95)00027-4
Wiley, 1998, Structure–activity relationships of indole- and pyrrole-derived cannabinoids, J Pharmacol Exp Ther, 285, 995
Wiley, 2011, 1-Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles in mice, Drug Alcohol Depend
Xi, 2011, Brain cannabinoid CB2 receptors modulate cocaine's actions in mice, Nat Neurosci, 14, 1160, 10.1038/nn.2874
Young, 2011, Cardiotoxicity associated with the synthetic cannabinoid, K9, with laboratory confirmation, Am J Emerg Med
Yücel, 2008, Regional brain abnormalities associated with long-term heavy cannabis use, Arch Gen Psychiatry, 65, 694, 10.1001/archpsyc.65.6.694
Zawilska, 2011, “Legal Highs” — new players in the old drama, Curr Drug Abuse Rev, 4, 122, 10.2174/1874473711104020122
Zimmermann, 2009, Withdrawal phenomena and dependence syndrome after the consumption of “Spice Gold”, Dtsch Artzebl Int, 106, 464
Zuba, 2011, Comparison of “herbal highs” composition, Anal Bioanal Chem, 400, 119, 10.1007/s00216-011-4743-7