AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and potency of novel synthetic cannabinoids in producing Δ9-Tetrahydrocannabinol-like effects in mice

Journal of Pharmacology and Experimental Therapeutics

Volumn 354, Issue 3, 2015, Pages 328-339

  Wiley, Jenny L ^a   Marusich, Julie A ^a   Lefever, Timothy W ^a   Antonazzo, Kateland R ^a   Wallgren, Michael T ^a   Cortes, Ricardo A ^a   Patel, Purvi R ^a   Grabenauer, Megan ^a   Moore, Katherine N ^a   Thomas, Brian F ^a  

^a RTI INTERNATIONAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (5 FLUOROPENTYL) 3 (1 NAPHTHOYL)INDOLE; 2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 3 (1 NAPHTHOYL) 1 PENTYLINDOLE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; 5 (1,1 DIMETHYLHEPTYL) 2 (3 HYDROXYCYCLOHEXYL)PHENOL; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID RECEPTOR AGONIST; DRONABINOL; N (1 AMINO 3 METHYL 1 OXOBUTAN 2 YL) 1 PENTYL 1H INDAZOLE 3 CARBOXAMIDE; N (1 AMINO 3 METHYLOXOBUTAN 2 YL) 1 (CYCLOHEXYLMETHYL) 1H INDAZOLE 3 CARBOXAMIDE; PSYCHOTROPIC AGENT; RIMONABANT; UNCLASSIFIED DRUG; [1 (5 FLUOROPENTYL) 1H BENZO[D]IMADAZOL 2 YL] (NAPHTHALEN 1 YL)METHANONE; ANALGESIC AGENT; CANNABINOID; ENDOCANNABINOID; STREET DRUG;

ADULT; ANIMAL BEHAVIOR; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; BINDING AFFINITY; CATALEPSY; CHEMICAL STRUCTURE; CONTROLLED STUDY; CONVULSION; DRUG BINDING SITE; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; HYDROXYLATION; HYPOTHERMIA; IMMOBILITY; IN VITRO STUDY; IN VIVO STUDY; MALE; METABOLITE; MOUSE; MOUSE MODEL; NONHUMAN; PRIORITY JOURNAL; RECEPTOR UPREGULATION; RECTUM TEMPERATURE; TOXICITY TESTING; TOXICOKINETICS; ANIMAL; C57BL MOUSE; CHEMICALLY INDUCED; DRUG EFFECTS; INSTITUTE FOR CANCER RESEARCH MOUSE; METABOLISM; MOTOR ACTIVITY;

ANALGESICS; ANIMALS; CANNABINOIDS; CATALEPSY; DRONABINOL; ENDOCANNABINOIDS; HYDROXYLATION; HYPOTHERMIA; MALE; MICE; MICE, INBRED C57BL; MICE, INBRED ICR; MOTOR ACTIVITY; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; STREET DRUGS;

EID: 84941557174     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.115.225326     Document Type: Article

References (31)

1. Bateman RH, Carruthers R, Hoyes JB, Jones C, Langridge JI, Millar A, Vissers JPC (2002) A novel precursor ion discovery methodon a hybrid quadrupole orthogonal acceleration time-of-flight (Q-TOF) mass spectrometer for studying protein phosphorylation. J Am Soc Mass Spectrom 13:792-803.
2. Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (1992a) Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol. J Pharmacol Exp Ther 263:1118-1126.
3. Compton DR, Johnson MR, Melvin LS, Martin BR (1992b) Pharmacological profile of a series of bicyclic cannabinoid analogs: classification as cannabimimetic agents. J Pharmacol Exp Ther 260:201-209.
4. Compton DR, Rice KC, De Costa BR, Razdan RK, Melvin LS, Johnson MR, Martin BR (1993) Cannabinoid structure-activity relationships: correlation of receptor binding and in vivo activities. J Pharmacol Exp Ther 265:218-226.
5. Devane WA, Dysarz FA 3rd, Johnson MR, Melvin LS, Howlett AC (1988) Determination and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol 34:605-613.
6. Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A, Mechoulam R (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258:1946-1949.
7. Drug Enforcement Administration, Department of Justice (2015) Schedules of controlled substances: Temporary placement of three synthetic cannabinoids into schedule I. Final order. Fed Regist 80:5042-5047.
8. Gaoni Y Mechoulam R (1964) Isolation, structure, and partial synthesis of an active constituent of hashish. J Am Chem Soc 86:1646-1647.
9. Gatch MB Forster MJ (2014) D9-Tetrahydrocannabinol-like discriminative stimulus effects of compounds commonly found in K2/Spice. Behav Pharmacol 25:750-757.
10. Gold LH, Balster RL, Barrett RL, Britt DT, Martin BR (1992) A comparison of the discriminative stimulus properties of delta 9-tetrahydrocannabinol and CP 55, 940 in rats and rhesus monkeys. J Pharmacol Exp Ther 262:479-486.
11. Grabenauer M, Krol WL, Wiley JL, Thomas BF (2012) Analysis of synthetic cannabinoids using high-resolution mass spectrometry and mass defect filtering: implications for nontargeted screening of designer drugs. Anal Chem 84:5574-5581.
12. Griffin G, Atkinson PJ, Showalter VM, Martin BR, Abood ME (1998) Evaluation of cannabinoid receptor agonists and antagonists using the guanosine-59-O-(3-[35S] thio)-triphosphate binding assay in rat cerebellar membranes. J Pharmacol Exp Ther 285:553-560.
13. Hanus L, Abu-Lafi S, Fride E, Breuer A, Vogel Z, Shalev DE, Kustanovich I, Mechoulam R (2001) 2-arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc Natl Acad Sci USA 98:3662-3665.
14. Huffman JW, Padgett LW (2005) Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes. Curr Med Chem 12:1395-1411.
15. Manera C, Tuccinardi T, Martinelli A (2008) Indoles and related compounds as cannabinoid ligands. Mini Rev Med Chem 8:370-387.
16. Martin BR, Compton DR, Thomas BF, PrescottWR, Little PJ, Razdan RK, Johnson MR, Melvin LS, Mechoulam R, Ward SJ (1991) Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs. Pharmacol Biochem Behav 40:471-478.
17. National Research Council (2011) Guide for the Care and Use of Laboratory Animals, National Academies Press, Washington, D.C.
18. Rinaldi-Carmona M, Barth F, Héaulme M, Shire D, Calandra B, Congy C, Martinez S, Maruani J, Néliat G, Caput D, et al. (1994) SR141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett 350: 240-244.
19. Showalter VM, Compton DR, Martin BR, Abood ME (1996) Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. J Pharmacol Exp Ther 278:989-999.
20. Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3, 4, 5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products. Forensic Toxicol 32: 105-115.
21. Vann RE, Warner JA, Bushell K, Huffman JW, Martin BR, Wiley JL (2009) Discriminative stimulus properties of delta9-tetrahydrocannabinol (THC) in C57Bl/6J mice. Eur J Pharmacol 615:102-107.
22. Vardakou I, Pistos C, Spiliopoulou Ch (2010) Spice drugs as a new trend: Mode of action, identification and legislation. Toxicol Lett 197:157-162.
23. Wiley JL, Barrett RL, Lowe J, Balster RL, Martin BR (1995a) Discriminative stimulus effects of CP 55, 940 and structurally dissimilar cannabinoids in rats. Neuropharmacology 34:669-676.
24. Wiley JL, Compton DR, Dai D, Lainton JA, Phillips M, Huffman JW, Martin BR (1998) Structure-activity relationships of indole- And pyrrole-derived cannabinoids. J Pharmacol Exp Ther 285:995-1004.
25. Wiley JL, Lefever TW, Cortes RA, Marusich JA (2014b) Cross-substitution of D9-tetrahydrocannabinol and JWH-018 in drug discrimination in rats. Pharmacol Biochem Behav 124:123-128.
26. Wiley JL, Lowe JA, Balster RL, Martin BR (1995b) Antagonism of the discriminative stimulus effects of delta 9-tetrahydrocannabinol in rats and rhesus monkeys. J Pharmacol Exp Ther 275:1-6.
27. Wiley JL, Martin BR (2009) Preclinical pharmacological and brain bioassay systems for CB1 cannabinoid receptors, in The Cannabinoid Receptors (Reggio PH ed) pp 329-360, Humana Press, New York.
28. Wiley JL, Marusich JA, Huffman JW (2014a) Moving around the molecule: Relationship between chemical structure and in vivo activity of synthetic cannabinoids. Life Sci 97:55-63.
29. Wiley JL, Marusich JA, Lefever TW, Grabenauer M, Moore KN, Thomas BF (2013) Cannabinoids in disguise: D9-tetrahydrocannabinol-like effects of tetramethylcyclopropyl ketone indoles. Neuropharmacology 75:145-154.
30. Wohlfarth A, Castaneto MS, Zhu M, Pang S, Scheidweiler KB, Kronstrand R, Huestis MA (2015) Pentylindole/pentylindazole synthetic cannabinoids and their 5-fluoro analogs produce different primary metabolites: Metabolite profiling for AB-PINACA and 5F-AB-PINACA. AAPS J 17:660-677.
31. Zhang Y, Gilliam A, Maitra R, Damaj MI, Tajuba JM, Seltzman HH, Thomas BF (2010) Synthesis and biological evaluation of bivalent ligands for the cannabinoid 1 receptor. J Med Chem 53:7048-7060.