Discriminative stimulus functions of methanandamide and ∆9-THC in rats: tests with aminoalkylindoles (WIN55,212-2 and AM678) and ethanol (original) (raw)
Abadji V, Lin S, Taha G, Griffin G, Stevenson LA, Pertwee RG, Makriyannis A (1994) (R)-Methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability. J Med Chem 37:1889–1893 ArticleCASPubMed Google Scholar
Alici T, Appel JB (2004) Increasing the selectivity of the discriminative stimulus effects of Δ9-tetrahydrocannabinol: complete generalization with methanandamide. Pharmacol Biochem Behav 79:431–437 ArticleCASPubMed Google Scholar
Basavarajappa BS, Hungund BL (2005) Role of the endocannabinoid system in the development of tolerance to alcohol. Alcohol Alcohol 40:15–24 CASPubMed Google Scholar
Bergman J, France CP, Holtzman SG, Katz JL, Koek W, Stephens DN (2000) Agonist efficacy, drug dependence, and medications development: preclinical evaluation of opioid, dopaminergic, and GABAA-ergic ligands. Psychopharmacology (Berl) 153:67–84 ArticleCAS Google Scholar
Bueno OFA, Carlini EA, Finkelfarb E, Suzuki J (1976) Delta-9-tetrahydrocannabinol, ethanol and amphetamine as discriminative stimuli—generalization tests with other drugs. Psychopharmacologia 46:235–243 ArticleCASPubMed Google Scholar
Burkey RT, Nation JR (1997) (R)-Methanandamide, but not anandamide, generalizes to Δ9-THC in a drug-discrimination procedure. Exp Clin Psychopharm 5:195–202 ArticleCAS Google Scholar
Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (1992) Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from Δ9-tetrahydrocannabinol. J Pharmacol Exp Ther 263:118–1126 Google Scholar
De Vry J, Jentzsch KR (2002) Discriminative stimulus effects of BAY 38-7271, a novel cannabinoid receptor agonist. Eur J Pharmacol 457:147–152 ArticlePubMed Google Scholar
De Vry J, Jentzsch KR (2004) Discriminative stimulus effects of the structurally novel cannabinoid CB1/CB2 receptor partial agonist BAY 59-3074 in the rat. Eur J Pharmacol 505:127–133 ArticlePubMed Google Scholar
Di Marzo V, Bisogno T, De Petrocellis L, Brandi I, Jefferson RG, Winckler RL, Davis JB, Dasse O, Mahadevan A, Razdan RK, Martin BR (2001) Highly selective CB(1) cannabinoid receptor ligands and novel CB(1)/VR(1) vanilloid receptor “hybrid” ligands. Biochem Biophys Res Commun 281:444–451 ArticlePubMed Google Scholar
Extance K, Goudie AJ (1981) Inter-animal olfactory cues in operant drug discrimination procedures in rats. Psychopharmacology (Berl) 73:363–371 ArticleCAS Google Scholar
Georgieva T, Devanathan S, Stropova D, Park CK, Salamon Z, Tollin G, Hruby VJ, Roeske WR, Yamamura HI, Varga E (2008) Unique agonist-bound cannabinoid CB(1) receptor conformations indicate agonist specificity in signaling. Eur J Pharmacol 581:19–29 ArticleCASPubMed Google Scholar
Glass M, Northup JK (1999) Agonist selective regulation of G proteins by cannabinoid CB(1) and CB(2) receptors. Mol Pharmacol 56:1362–1369 CASPubMed Google Scholar
Howlett AC (2004) Efficacy in CB1 receptor-mediated signal transduction. Br J Pharmacol 142:1209–1218 ArticleCASPubMed Google Scholar
Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, Reggio PH, Wiley JL, Martin BR (2003) 3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor. Bioorg Med Chem 11:539–549 ArticleCASPubMed Google Scholar
Järbe TUC (1977) Alcohol discrimination in gerbils: Interactions with bemegride, DH-524, d-amphetamine, and delta-9-THC. Arch Int Pharmacodyn Ther 227:118–129 PubMed Google Scholar
Järbe TUC, Lamb RJ, Makriyannis A, Lin S, Goutopoulos A (1998) Δ9-THC training dose as a determinant for (R)-methanandamide generalization in rats. Psychopharmacology (Berl) 140:519–522 Article Google Scholar
Järbe TUC, Lamb RJ, Lin S, Makriyannis A (2000) Δ9-THC training dose as a determinant for (R)-methanandamide generalization in rats: a systematic replication. Behav Pharmacol 11:81–86 PubMed Google Scholar
Järbe TUC, Lamb RJ, Lin S, Makriyannis A (2001) (R)-Methanandamide and Δ9-THC as discriminative stimuli in rats: tests with the cannabinoid antagonist SR-141716 and the endogenous ligand anandamide. Psychopharmacology (Berl) 156:369–380 Article Google Scholar
Järbe TUC, DiPatrizio NV, Li C, Makriyannis A (2003a) 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 ArticlePubMed Google Scholar
Järbe TUC, Lamb RJ, Liu Q, Makriyannis A (2003b) (R)-Methanandamide and Δ9-THC induced operant rate decreases in rats are not readily antagonized by SR-141716A. Eur J Pharmacol 466:121–127 ArticlePubMed Google Scholar
Järbe TUC, Harris MY, Li C, Liu Q, Makriyannis A (2004) Discriminative stimulus effects in rats of SR-141716 (rimonabant), a cannabinoid CB1 receptor antagonist. Psychopharmacology (Berl) 177:35–45 Article Google Scholar
Järbe TUC, Lamb RJ, Liu Q, Makriyannis A (2006a) Discriminative stimulus functions of AM-1346, a CB1R selective anandamide analog in rats trained with Δ9-THC or (R)-methanandamide (AM-356). Psychopharmacology (Berl) 188:315–323 Article Google Scholar
Järbe TUC, Liu Q, Makriyannis A (2006b) Antagonism of the discriminative stimulus effects of Δ9-THC and (R)-methanandamide in rats. Psychopharmacology (Berl) 184:36–45 Article Google Scholar
Järbe TUC, Li C, Vadivel SK, Makriyannis A (2008) Discriminative stimulus effects of the cannabinoid CB1 receptor antagonist rimonabant in rats. Psychopharmacology (Berl) 198:467–478 Article Google Scholar
Järbe TUC, Li C, Liu Q, Makriyannis A (2009) Discriminative stimulus functions in rats of AM1346, a high-affinity CB1R selective anandamide analog. Psychopharmacology (Berl) 203:229–239 Article Google Scholar
Khanolkar AD, Abadji V, Lin S, Hill WAG, Taha G, Abouzid K, Meng Z, Fan P, Makriyannis A (1996) Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem 39:4515–4519 ArticleCASPubMed Google Scholar
Kubena RK, Barry H III (1972) Stimulus characteristics of marihuana components. Nature 235:397–398 ArticleCASPubMed Google Scholar
Lamb RJ, Järbe TUC (2001) Effects of fluvoxamine on ethanol-reinforced behavior in the rat. J Pharmacol Exp Ther 297:1001–1009 CASPubMed Google Scholar
Mauler F, Mittendorf J, Horváth E, de Vry J (2002) Characterization of the diarylether sulfonylester ()-(R)-3-(2-hydroxymethylindanyl-4-oxy)phenyl-4, 4, 4-trifluoro-1-sulfonate (BAY 38-7271) as a potent cannabinoid receptor agonist with neuroprotective properties. J Pharmacol Exp Ther 302:359–368 ArticleCASPubMed Google Scholar
McMahon LR (2006a) Characterization of cannabinoid agonists and apparent pA2 analysis of cannabinoid antagonists in rhesus monkeys discriminating Δ9-tetrahydrocannabinol. J Pharmacol Exp Ther 319:1211–1218 ArticleCASPubMed Google Scholar
McMahon LR (2006b) Discriminative stimulus effects of the cannabinoid CB1 antagonist SR 141716A in rhesus monkeys pretreated with Δ9-tetrahydrocannabinol. Psychopharmacology (Berl) 188:306–314 ArticleCAS Google Scholar
McMahon LR (2009) Apparent affinity estimates of rimonabant in combination with anandamide and chemical analogs of anandamide in rhesus monkeys discriminating Δ9-tetrahydrocannabinol. Psychopharmacology (Berl) 203:219–228 ArticleCAS Google Scholar
McMahon LR, Ginsburg BC, Lamb RJ (2008) Cannabinoid agonists differentially substitute for the discriminative stimulus effects of Δ9-tetrahydrocannabinol in C57BL/6J mice. Psychopharmacology (Berl) 198:487–495 ArticleCAS Google Scholar
Mukhopadhyay S, Howlett AC (2005) Chemically distinct ligands promote differential CB1 cannabinoid receptor–Gi protein interactions. Mol Pharmacol 67:2016–2024 ArticleCASPubMed Google Scholar
National Institutes of Health (1996) Principles of animal laboratory care. National Academy, Washington, D.C Google Scholar
Oz M (2006) Receptor-independent actions of cannabinoids on cell membranes: focus on endocannabinoids. Pharmacol Ther 111:114–144 ArticleCASPubMed Google Scholar
Pacher P, Batkai S, Kunos G (2006) The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol Rev 58:389–462 ArticleCASPubMed Google Scholar
Pério A, Rinaldi-Carmona M, Maruani J, Barth F, Le Fur G, Soubrié P (1996) Central mediation of the cannabinoid cue: activity of a selective CB1 antagonist, SR 141716A. Behav Pharmacol 7:65–71 ArticlePubMed Google Scholar
Pertwee RG (2008) Ligands that target cannabinoids receptors in the brain: from THC to anandamide and beyond. Addict Biol 13:147–159 ArticleCASPubMed Google Scholar
Saidak Z, Blake-Palmer K, Hay DL, Northup JK, Glass M (2006) Differential activation of G-proteins by mu-opioid receptor agonists. Br J Pharmacol 147:671–680 ArticleCASPubMed Google Scholar
Solinas M, Panlilio LV, Justinova Z, Yasar S, Goldberg SR (2006) Using drug-discrimination techniques to study the abuse-related effects of psychoactive drugs in rats. Nat Protoc 1:1194–1206 ArticleCASPubMed Google Scholar
Solinas M, Scherma M, Fattore L, Stroik J, Wertheim C, Tanda G, Fratta W, Goldberg SR (2007a) Nicotinic alpha 7 receptors as a new target for treatment of cannabis abuse. J Neurosci 27:5615–5620 ArticleCASPubMed Google Scholar
Solinas M, Tanda G, Justinova Z, Wertheim CE, Yasar S, Piomelli D, Vadivel SK, Makriyannis A, Goldberg SR (2007b) 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 ArticleCASPubMed Google Scholar
Tai S, Järbe TUC, Li C, Vadivel SK, Makriyannis A (2009) Discriminative stimulus functions of methanandamide and ∆9-THC in rats: tests with aminoalkylindoles (WIN55, 212-2 and AM678) and ethanol. International Cannabinoid Research Society (ICRS), Burlington Google Scholar
Thakur GA, Nikas SP, Li C, Makriyannis A (2005) Structural requirements for cannabinoid receptor probes. Handb Exp Pharmacol 168:209–246 ArticleCASPubMed Google Scholar
Vann RE, Cook CD, Martin BR, Wiley JL (2007) Cannabimimetic properties of ajulemic acid. J Pharmacol Exp Ther 320:678–686 ArticleCASPubMed Google Scholar
Vann RE, Warner JA, Bushell K, Huffman JW, Martin BR, Wiley JL (2009) Discriminative stimulus properties of Δ9-tetrahydrocannabinol (THC) in C57BL/6J mice. Eur J Pharmacol 615:102–107 ArticleCASPubMed Google Scholar
Wallace MJ, Newton PM, McMahon T, Connolly J, Huibers A, Whistler J, Messing RO (2009) PKCepsilon regulates behavioral sensitivity, binding and tolerance to the CB1 receptor agonist WIN55, 212-2. Neuropsychopharmacology 34:1733–1742 ArticleCASPubMed Google Scholar
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 ArticleCASPubMed Google Scholar
Wiley JL, Lowe JA, Balster RL, Martin BR (1995b) Antagonism of the discriminative stimulus effects of Δ9-tetrahydrocannabinol in rats and rhesus monkeys. J Pharmacol Exp Ther 275:1–6 CASPubMed Google Scholar
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 CASPubMed Google Scholar
Wiley JL, LaVecchia KL, Karp NE, Kulasegram S, Mahadevan A, Razdan RK, Martin BR (2004) A comparison of the discriminative stimulus effects of Δ9-tetrahydrocannabinol and O-1812, a potent and metabolically stable anandamide analog, in rats. Exp Clin Psychopharmacol 12:173–179 ArticleCASPubMed Google Scholar