Discriminative stimulus functions in rats of AM1346, a high-affinity CB1R selective anandamide analog

Psychopharmacology

Volumn 203, Issue 2, 2009, Pages 229-239

  Järbe, Torbjörn U C ^a,c   Li, Chen ^b   Liu, Qian ^b   Makriyannis, Alexandros ^c  

^a TEMPLE UNIVERSITY   (United States)

^b UNIVERSITY OF CONNECTICUT   (United States)

^c NORTHEASTERN UNIVERSITY   (United States)

Author keywords

9 THC; Anandamide analogs AM 1346 and mAEA; Drug discrimination; I.e.; R (+) methanandamide ; Rats; Rimonabant

Indexed keywords

AM 1346; ANANDAMIDE; CANNABINOID 1 RECEPTOR; DEXAMPHETAMINE; DRONABINOL; METHANANDAMIDE; MORPHINE; RIMONABANT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DISCRIMINATIVE STIMULUS; DISSOCIATION; DRUG HALF LIFE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; IN VIVO STUDY; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR BINDING; RECEPTOR UPREGULATION;

ANIMALS; ARACHIDONIC ACIDS; DISCRIMINATION (PSYCHOLOGY); DOSE-RESPONSE RELATIONSHIP, DRUG; LIGANDS; MALE; PIPERIDINES; POLYUNSATURATED ALKAMIDES; PYRAZOLES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, CANNABINOID, CB1; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROCANNABINOL;

EID: 62449333570     PISSN: 00333158     EISSN: 14322072     Source Type: Journal    
DOI: 10.1007/s00213-008-1199-3     Document Type: Article

References (46)

1. V Abadji S Lin G Taha G Griffin LA Stevenson RG Pertwee A Makriyannis 1994 (R)-Methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability J Med Chem 37 1889 1893
2. 9-tetrahydrocannabinol: complete generalization with methanandamide Pharmacol Biochem Behav 79 431 437
3. 9-Tetrahydrocannabinol discrimination in rats as a model for cannabis intoxication Neurosci Biobehav Rev 16 55 62
4. RL Barrett JL Wiley RL Balster BR Martin 1995 Pharmacological specificity of delta-9-tetrahydrocannabinol discrimination in rats Psychopharmacology (Berl) 118 419 424
5. 9-tetrahydrocannabinol and methanandamide in CB1 knockout and wild-type mice J Pharmacol Exp Ther 309 86 91
6. DW Bonhaus LK Chang J Kwan GR Martin 1998 Dual activation and inhibition of adenylyl cyclase by cannabinoid receptor agonists: evidence for agonist-specific trafficking of intracellular responses J Pharmacol Exp Ther 287 884 888
7. AJ Brown 2007 Novel cannabinoid receptors Br J Pharmacol 152 567 575
8. RG Browne A Weissman 1981 Discriminative stimulus properties of delta-9-tetrahydrocannabinol: mechanistic studies J Clin Pharmacol 21 Suppl 227S 234S
9. 9-THC in a drug-discrimination procedure Exp Clin Psychopharm 5 195 202
10. BF Cravatt DK Giang SP Mayfield DL Boger RA Lerner NB Gilula 1996 Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides Nature 384 83 87
11. K Extance AJ Goudie 1981 Inter-animal olfactory cues in operant drug discrimination procedures in rats Psychopharmacology (Berl) 73 363 371
12. T Georgieva S Devanathan D Stropova CK Park Z Salamon G Tollin VJ Hruby WR Roeske HI Yamamura E Varga 2008 Unique agonist-bound cannabinoid CB(1) receptor conformations indicate agonist specificity in signaling Eur J Pharmacol 581 19 29
13. LH Gold RL Balster RL Barrett DT Britt BR Martin 1992 A comparison of the discriminative stimulus properties of delta9-tetrahydrocannabinol and CP 55,940 in rats and rhesus monkeys J Pharmacol Exp Ther 262 479 486
14. DB Houston AC Howlett 1998 Differential receptor-G-protein coupling evoked by dissimilar cannabinoid receptor agonists Cell Signal 9 667 674
15. AC Howlett 2004 Efficacy in CB1 receptor-mediated signal transduction Br J Pharmacol 142 1209 1218
16. Järbe TUC, Mathis DA (1992) Dissociative and discriminative stimulus functions of cannabinoids and cannabinergics. In: Bartke A, Murphy L (eds) Marijuana/cannabinoids: neurobiology and neurophysiology. CRC, Boca Raton FL, pp 425-459
17. TUC Järbe MDB Swedberg R Mechoulam 1981 A repeated tests procedure to assess onset and duration of the cue properties of (-)-delta-9-THC, (-)-delta-8-THC-DMH and (+)-delta-8-THC Psychopharmacology (Berl) 75 152 157
18. TUC Järbe AJ Hiltunen N Lander R Mechoulam 1986 Cannabinergic activity (delta-1-THC cue) of cannabidiol monomethyl ether and two stereoisomeric hexahydrocannabinols in rats and pigeons Pharmacol Biochem Behav 25 393 399
19. 9-THC training dose as a determinant for (R)-methanandamide generalization in rats Psychopharmacology (Berl) 140 519 522
20. TUC Järbe R Sheppard RJ Lamb A Makriyannis S Lin A Goutopoulos 1998 Effects of delta-9-tetrahydrocannabinol and (R)-methanandamide on open-field behavior in rats Behav Pharmacol 9 169 174
21. 9-THC training dose as a determinant for (R)-methanandamide generalization in rats: a systematic replication Behav Pharmacol 11 81 86
22. 9-THC as discriminative stimuli in rats: tests with the cannabinoid antagonist SR-141716 and the endogenous ligand anandamide Psychopharmacology (Berl) 156 369 380
23. TUC Järbe NV DiPatrizio C Li A Makriyannis 2003 The cannabinoid receptor antagonist SR-141716 does not readily antagonize open-field effects induced by the cannabinoid receptor agonist (R)-methanandamide in rats Pharmacol Biochem Behav 75 809 821
24. 9-THC induced operant rate decreases in rats are not readily antagonized by SR-141716A Eur J Pharmacol 466 121 127
25. 9-THC or (R)-methanandamide (AM-356) Psychopharmacology (Berl) 188 315 323
26. TUC Järbe NV DiPatrizio C Li A Makriyannis 2007 Effects of AM1346, a high-affinity CB1 receptor selective anandamide analog, on open-field behavior in rats Behav Pharmacol 18 673 680
27. Järbe TUC, Li C, Vadivel SK, Makriyannis A (2008) Discriminative stimulus effects of the cannabinoid CB(1) receptor antagonist rimonabant in rats. Psychopharmacology (Berl) (in press). DOI 10.1007/s00213-008-1076-0
28. AD Khanolkar A Makriyannis 1999 Structure-activity relationships of anandamide, an endogenous cannabinoid ligand Life Sci 65 607 616
29. S Lin AD Khanolkar P Fan A Goutopoulos C Qin D Papahadjis A Makriyannis 1998 Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability J Med Chem 41 5353 5361
30. 9-tetrahydrocannabinol J Pharmacol Exp Ther 319 1211 1218
31. 9-tetrahydrocannabinol in C57BL/6J mice. Psychopharmacology (Berl) (in press). DOI 10.1007/s00213-007-0900-2
32. S Mukhopadhyay AC Howlett 2005 Chemically distinct ligands promote differential CB1 cannabinoid receptor-Gi protein interactions Mol Pharmacol 67 2016 2024
33. National Institutes of Health (1996) Principles of animal laboratory care. National Academy Press, Washington, DC
34. M Oz 2006 Receptor-independent actions of cannabinoids on cell membranes: focus on endocannabinoids Pharmacol Ther 111 114 144
35. P Pacher S Batkai G Kunos 2006 The endocannabinoid system as an emerging target of pharmacotherapy Pharmacol Rev 58 389 462
36. RP Picone AD Khanolkar W Xu LA Ayotte GA Thakur DP Hurst ME Abood PH Reggio DJ Fournier A Makriyannis 2005 (-)-7-Isothiocyanato-11-hydroxy-1,1- dimethylheptylhexahydro-cannabinol (AM841), a high-affinity electrophilic ligand, interacts covalently with a cysteine in helix six and activates the CB1 cannabinoid receptor Mol Pharmacol 68 1623 1635
37. 1 cannabinoid receptor and multiple pathways for conformational induction J Chem Inf Model 46 1286 1300
38. Sidman M (1960) Tactics of scientific research-evaluating experimental data in psychology. Basic Books, NY, New York
39. M Solinas G Tanda Z Justinova CE Wertheim S Yasar D Piomelli SK Vadivel A Makriyannis SR Goldberg 2007 The endogenous cannabinoid anandamide produces Δ9-tetrahydrocannabinol-like discriminative and neurochemical effects that are enhanced by inhibition of fatty acid amide hydrolase but not by inhibition of anandamide transport J Pharmacol Exp Ther 321 370 380
40. M Solinas S Yasar SR Goldberg 2007 Endocannabinoid system involvement in brain reward processes related to drug abuse Pharmacol Res 56 393 405
41. J Vinklerová J Nováková A Sulcová 2002 Inhibition of methamphetamine self-administration in rats by cannabinoid receptor antagonist AM 251 J Psychopharmacol 16 139 143
42. Weissman A (1978) Generalization of the discriminative stimulus properties of delta-9-tetrahydrocannabinol to cannabinoids with therapeutic potential. In: Colpaert FC, Rosecrans JA (eds) Stimulus properties of drugs: ten years of progress. Elsevier/North Holland Biomed, Amsterdam, pp 99-122
43. JL Wiley 1999 Cannabis: discrimination of "internal bliss"? Pharmacol Biochem Behav 64 257 260
44. JL Wiley WJ Ryan RK Razdan BR Martin 1998 Evaluation of cannabimimetic effects of structural analogs of anandamide in rats Eur J Pharmacol 355 113 118
45. 9-tetrahydrocannabinol and O-1812, a potent and metabolically stable anandamide analog, in rats Exp Clin Psychopharmacol 12 173 179
46. 9-tetrahydrocannabinol and anandamide analogs in mice Eur J Pharmacol 510 59 68