Native CB1 receptor affinity, intrinsic activity and accumbens shell dopamine stimulant properties of third generation SPICE/K2 cannabinoids: BB-22, 5F-PB-22, 5F-AKB-48 and STS-135

Neuropharmacology

Volumn 105, Issue , 2016, Pages 630-638

  De Luca, Maria Antonietta ^a   Castelli, M Paola ^a   Loi, Barbara ^b   Porcu, Alessandra ^a   Martorelli, Mariella ^a   Miliano, Cristina ^a   Kellett, Kathryn ^b   Davidson, Colin ^c   Stair, Jacqueline L ^b   Schifano, Fabrizio ^b   Di Chiara, Gaetano ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

^b UNIVERSITY OF HERTFORDSHIRE   (United Kingdom)

^c ST GEORGE'S UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Cannabinoids; CB1 receptors; Dopamine; GTP S binding; K2; Microdialysis; Spice

Indexed keywords

CANNABINOID 1 RECEPTOR; CANNABINOID DERIVATIVE; DOPAMINE; GUANINE NUCLEOTIDE BINDING PROTEIN; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); 1 (2,4 DICHLOROPHENYL) 5 (4 IODOPHENYL) 4 METHYL N (1 PIPERIDYL) 1H PYRAZOLE 3 CARBOXAMIDE; 1-(CYCLOHEXYLMETHYL)-1H-INDOLE-3-CARBOXYLIC ACID 8-QUINOLINYL ESTER; 1-PENTYFLUORO-1H-INDOLE-3-CARBOXYLIC ACID 8-QUINOLINYL ESTER; 1-PENTYL-3-(1-NAPHTHOYL)INDOLE; ADAMANTANE; CANNABINOID RECEPTOR AGONIST; CANNABINOID RECEPTOR ANTAGONIST; CENTRAL STIMULANT AGENT; CNR1 PROTEIN, MOUSE; CNR1 PROTEIN, RAT; DOPAMINE RECEPTOR STIMULATING AGENT; INDAZOLE DERIVATIVE; INDOLE DERIVATIVE; N-(1-ADAMANTYL)-1-(5-FLUOROPENTYL)-1H-INDAZOLE-3-CARBOXAMIDE; N-(ADAMANTAN-1-YL)-1-(5-FLUOROPENTYL)-1H-INDOLE-3-CARBOXAMIDE; NAPHTHALENE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRAZOLE DERIVATIVE; QUINOLINE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN CORTEX; BRAIN HOMOGENATE; CONTROLLED STUDY; EC50; IN VITRO STUDY; LETHALITY; MALE; MEDIAL PREFRONTAL CORTEX; MOUSE; NONHUMAN; NUCLEUS ACCUMBENS SHELL; PRIORITY JOURNAL; RAT; RECEPTOR AFFINITY; RECEPTOR BINDING; AGONISTS; ANALOGS AND DERIVATIVES; ANIMAL; ANTAGONISTS AND INHIBITORS; C57BL MOUSE; CHEMICAL STRUCTURE; DOSE RESPONSE; DRUG EFFECTS; GENETICS; KNOCKOUT MOUSE; METABOLISM; NUCLEUS ACCUMBENS; PRECLINICAL STUDY; PREFRONTAL CORTEX; SPRAGUE DAWLEY RAT;

ADAMANTANE; ANIMALS; CANNABINOID RECEPTOR AGONISTS; CANNABINOID RECEPTOR ANTAGONISTS; CENTRAL NERVOUS SYSTEM STIMULANTS; DOPAMINE AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; INDAZOLES; INDOLES; MALE; MICE, INBRED C57BL; MICE, KNOCKOUT; MOLECULAR STRUCTURE; NAPHTHALENES; NUCLEUS ACCUMBENS; PIPERIDINES; PREFRONTAL CORTEX; PYRAZOLES; QUINOLINES; RATS, SPRAGUE-DAWLEY; RECEPTOR, CANNABINOID, CB1;

EID: 84962214785     PISSN: 00283908     EISSN: 18737064     Source Type: Journal    
DOI: 10.1016/j.neuropharm.2015.11.017     Document Type: Article

References (43)

1. Advisory Council on the Misuse of Drugs (ACMD) Consideration of the Major Cannabinoid Agonists 2009 Home Office London
2. Advisory Council on the Misuse of Drugs (ACMD) Further Consideration of Synthetic Cannabinoids 2012 Home Office London
3. Advisory Council on the Misuse of Drugs (ACMD) Third Generation'' Synthetic Cannabinoids 2014 Home Office London
4. B.K. Atwood, J. Huffman, A. Straiker, and K. Mackie JWH018, a common constituent of 'Spice' herbal blends, is a potent and efficacious cannabinoid CB(1) receptor agonist Br. J. Pharmacol. 160 2010 585 593
5. B.K. Atwood, D. Lee, A. Straiker, T.S. Widlanski, and K. Mackie CP 47,497-C8 and JWH073, commonly found in 'Spice' herbal blends, are potent and efficacious CB(1)cannabinoid receptor agonists Eur. J. Pharmacol. 659 2011 139 145
6. V. Auwarter, P.I. Dargan, and D.M. Wood Paul I. Dargan, David M. Wood, Synthetic Cannabinoid Receptor Agonists. Chapter in: Novel Psychoactive Substances 2013 Elsevier
7. L.K. Brents, and P.L. Prather The K2/Spice phenomenon: emergence, identification, legislation and metabolic characterization of synthetic cannabinoids in herbal incense products Drug Metab. Rev. Feb. 46 1 2014 72 85
8. L.K. Brents, E.E. Reichard, S.M. Zimmerman, J.H. Moran, W.E. Fantegrossi, and P.L. Prather 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 2011 e21917
9. M.S. Castaneto, A. Wohlfarth, N.A. Desrosiers, R.L. Hartman, D.A. Gorelick, and M.A. Huestis Synthetic cannabinoids pharmacokinetics and detection methods in biological matrices Drug Metab. Rev. 47 2 2015 May 124 174
10. Y.C. Cheng, and W.H. Prusoff Relationship between the inhibition constant (Ki) and the concentration of inhibition which causes 50% inhibition (IC50) of an enzyme reaction Biochem. Pharmacol. 22 1973 3099 3108
11. M.A. De Luca, M. Solinas, Z. Bimpisidis, S.R. Goldberg, and G. Di Chiara Cannabinoid facilitation of behavioral and biochemical hedonic taste responses Neuropharmacology 63 1 2012 Jul 161 168 10.1016/j.neuropharm.2011.10.018 Epub 2011 Nov 2. PubMed PMID: 22063718; PubMed Central PMCID: PMC3705914
12. M.A. De Luca, V. Valentini, Z. Bimpisidis, F. Cacciapaglia, P. Caboni, and G. Di Chiara Endocannabinoid 2-Arachidonoylglycerol self-administration by Sprague-Dawley rats and stimulation of in vivo dopamine transmission in the nucleus accumbens shell Front. Psychiatry 5 2014 Oct 17 140 10.3389/fpsyt.2014.00140 eCollection 2014. PubMed PMID: 25368584; PubMed Central PMCID: PMC4201088
13. M.A. De Luca, Z. Bimpisidis, M. Melis, M. Marti, P. Caboni, V. Valentini, G. Margiani, N. Pintori, I. Polis, G. Marsicano, L.H. Parsons, and G. Di Chiara Stimulation of in vivo dopamine transmission and intravenous self-administration in rats and mice by JWH-018, a spice cannabinoid Neuropharmacology 99 2015 Oct 6 705 714 10.1016/j.neuropharm.2015.08.041 [Epub ahead of print] PubMed PMID: 26327678
14. W.A. Devane, F.A. Dysarz 3rd, M.R. Johnson, L.S. Melvin, and A.C. Howlett Determination and characterization of a cannabinoid receptor in rat brain Mol. Pharmacol. 34 1988 605 613
15. G. Di Chiara, V. Bassareo, S. Fenu, M.A. De Luca, L. Spina, C. Cadoni, E. Acquas, E. Carboni, V. Valentini, and D. Lecca Dopamine and drug addiction: the nucleus accumbens shell connection Neuropharmacology 47 Suppl. 1 2004 227 241 Review. PubMed PMID: 15464140
16. EMCDDA, European Monitoring Centre for Drugs and Drug Addiction Understanding the 'Spice' Phenomenon 2009 EMCDDA Thematic Paper, Publications Office of the European Union Luxembourg
17. J.W. Huffman, G. Zengin, M.J. Wu, J. Lu, G. Hynd, K. Bushell, A.L. Thompson, S. Bushell, C. Tartal, D.P. Hurst, P.H. Reggio, D.E. Selley, M.P. Cassidy, J.L. Wiley, and B.R. Martin Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists Bioorg Med. Chem. 13 2005 89 112
18. L.D. Johnston, P.M. O'Malley, J.G. Bachman, and J.E. Schulenberg Monitoring the Future National Survey Results on Drug Use, 1975-2012. Volume I: Secondary School Students 2013 Institute for Social Research, The University of Michigan Ann Arbor 604
19. D. Lecca, F. Cacciapaglia, V. Valentini, and G. Di Chiara Monitoring extracellular dopamine in the rat nucleus accumbens shell and core during acquisition and maintenance of intravenous WIN 55,212-2 self-administration Psychopharmacol. Berl. 188 1 2006 Sep 63 74 Epub 2006 Jul 19. PubMed PMID: 16850116
20. C. Manera, V. Benetti, M.P. Castelli, T. Cavallini, S. Lazzarotti, F. Pibiri, G. Saccomanni, T. Tuccinardi, A. Vannacci, A. Martinelli, and P.L. Ferrarini Design, synthesis, and biological evaluation of new 1,8-naphthyridin-4(1H)-on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives as CB2 selective agonists J. Med. Chem. 49 2006 5947 5957
21. R. Marshell, T. Kearney-Ramos, L.K. Brents, W.S. Hyatt, S. Tai, P.L. Prather, and W.E. Fantegrossi In vivo effects of synthetic cannabinoids JWH-018 and JWH-073 and phytocannabinoid Δ9-THC in mice: inhalation versus intraperitoneal injection Pharmacol. Biochem. Behav. 124 2014 40 47
22. D. Papanti, F. Schifano, T. Bonavigo, G. Botteon, F. Bertossi, J. Mannix, M. Impagnatiello, and E. Pascolo-Fabrici 'Spiceophrenia': a systematic overview of 'Spice'-related psychopathological issues and a case report Hum. Psychopharmacol. Clin. Exp. 28 2013 379 389
23. G.D. Papanti, L. Orsolini, G. Francesconi, and F. Schifano "Noids" in a nutshell: everything you (don't) want to know about synthetic cannabimimetics Adv. Dual Diagn. 7 2014 1 13
24. G. Paxinos, and C. Watson The Rat Brain in Stereotaxic Coordinates fourth ed. 1998 Academic Press San Diego, CA
25. R.G. Pertwee Pharmacological actions of cannabinoids Handb. Exp. Pharmacol. 168 2005 1 51 Review. PubMed PMID: 16596770
26. Plymouth Herald, 2015. Available from: http://www.plymouthherald.co.uk.
27. F.E. Pontieri, G. Tanda, and G. Di Chiara Intravenous cocaine, morphine, and amphetamine preferentially increase extracellular dopamine in the "shell" as compared with the "core" of the rat nucleus accumbens Proc. Natl. Acad. Sci. U. S. A. 92 26 1995 Dec 19 12304 12308
28. F.E. Pontieri, G. Tanda, F. Orzi, and G. Di Chiara Effects of nicotine on the nucleus accumbens and similarity to those of addictive drugs Nature 382 6588 1996 Jul 18 255 257 PubMed PMID: 8717040
29. R. Santacroce, O. Corazza, G. Martinotti, F.S. Bersani, G. Valeriani, and M. Di Giannantonio Psyclones: a roller coaster of life? Hidden synthetic cannabinoids and stimulants in apparently harmless products Hum. Psychopharmacol. 30 2015 265 271
30. F. Schifano, L. Orsolini, D. Papanti, and J. Corkery Novel psychoactive substances of interest for psychiatry World Psychiatry 14 2015 15 26
31. J. Schlatter Atta-ur- Rahman, Chapter in Studies in Natural Products Chemistry 2014 Elsevier
32. P.L. Simonato, O. Corazza, P. Santonastaso, J. Corkery, P. Deluca, Z. Davey, U. Blaszko, and F. Schifano Novel psychoactive substances as a novel challenge for health professionals; results from an Italian survey Hum. Psychopharmacol. Clin. Exp. 28 2013 324 331
33. M. Spaderna, P.H. Addy, and D.C. D'Souza Spicing things up: synthetic cannabinoids Psychopharmacol. Berl. 228 2013 525 540
34. G. Tanda, F.E. Pontieri, and G. Di Chiara Cannabinoid and heroin activation of mesolimbic dopamine transmission by a common mu1 opioid receptor mechanism Science 276 5321 1997 Jun 27 2048 2050 PubMed PMID: 9197269
35. B.F. Thomas, A.F. Gilliam, D.F. Burch, M.J. Roche, and H.H. Seltzman Comparative receptor binding analyses of cannabinoid agonists and antagonists J. Pharmacol. Exp. Ther. 285 1998 285 292
36. N. Uchiyama, M. Kawamura, R. Kikura-Hanajiri, and Y. Goda Identification of Two New-type Synthetic Cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1Hindazole-3-carboxamide (APINACA), and Detection of Five Synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as Designer Drugs in Illegal Products Forensic Toxicol. 30 2012 114 125
37. N. Uchiyama, M. Kawamura, R. Kikura-Hanajiri, and Y. Goda URB-754:a new class of designer drug and 12 synthetic cannabinoids detected in illegal products Forensic Sci. Int. 227 2013 21 32
38. N. Uchiyama, S. Matsuda, M. Kawamura, R. Kikura-Hanajiri, and Y. Goda Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADBFUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products Forensic Toxicol. 31 2013 223 240
39. J. van Amsterdam, T. Brunt, and W. van den Brink The adverse health effects of synthetic cannabinoids with emphasis on psychosis-like effects J. Psychopharmacol. 29 3 2015 254 263
40. A. Vigolo, A. Ossato, C. Trapella, F. Vincenzi, C. Rimondo, C. Seri, K. Varani, G. Serpelloni, and M. Marti Novel halogenated derivates of JWH-018: behavioral and binding studies in mice Neuropharmacology 95 2015 68 82
41. Wedinos Philtre Issue No. 3 2014 Available from: http://www.wedinos.org/resources/downloads/Philtre-Issue-3.pdf (accessed on 3rd August 2015)
42. J.L. Wiley, J.A. Marusich, B.R. Martin, and J.W. Huffman 1-Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles in mice Drug Alcohol Depend. 123 2012 148 153
43. J.B. Zawilska, and J. Wojcieszak Spice/K2 drugs-more than innocent substitutes for marijuana Int. J. Neuropsychopharmacol. 17 3 2014 Mar 509 525 10.1017/S1461145713001247 Epub 2013 Oct 29. Review. PubMed PMID: 24169044