135
Views
35
CrossRef citations to date
0
Altmetric
Review

Cannabinoid receptor agonists and antagonists

Pages 301-313 | Published online: 25 Feb 2005

Bibliography

  • GAONI Y, MECHOULAM R: Isolation,structure,andpar-tialsynthesisofanactiveconstituentofhashish.J. Am. Chem. Soc.(1964) 86: 1646-1647.
  • MECHOULAM R: Thepharmacohistoryofcannabissa-tiva.In: Cannabinoids as Therapeutic Agents.Mechoulam R (Ed.), CRC Press, Boca Raton (1986) 1–20.
  • RAZDAN RK, HOWES JF: Drugsrelatedtotetrahydro-cannabinol.Med. Res. Rev.(1983) 3:119–146.
  • CONSROE P, SANDYK R: Potentialroleofcannabinoidsfortherapyofneurologicaldisorders.In: Mari-juana/Cannabinoids: Neurobiology and Neurophysiology. Murphy L, Bartke A (Eds.), CRC Press, Boca Raton (1992) 459–524.
  • DEVANE WA, DYSARZ III F A, JOHNSON MR et al:Deter-mination and characterisation of a cannabinoid recep-torinratbrain.Mol. Pharmacol(1988) 34:605–613.
  • MATSUDA LA, STEPHEN SJ, BROWNSTEIN MJ et al:Struc-ture of a cannabinoid receptor and functional expres-sionoftheclonedcDNA.Nature (London)(1990) 346:561–564.
  • MUNRO S, THOMAS KL, ABU-SHAR M: Molecularcharac-terisation of a peripheral receptor for cannabinoids. Nature (London)(1993) 365:61–65.
  • DEVANE WA, HANUS L, BREUER A et al.:Isolationandstructure of a brain constituent that binds to the can-nabinoidreceptor.Science(1992) 258:1946–1949.
  • MATSUDA LA, BONNER TI: Molecularbiologyofthecan-nabinoidreceptors.In: Cannabinoid Receptors.Pertwee RG (Ed.), Academic Press, London (1995) 17–143.
  • ONAIVI ES, CHAKRABARTI A, CHAUDHURI G: Cannabi-noidreceptorgenes.Prog. Neurobiol.(1996) 48:275–305.
  • HOWLETT AC: Pharmacologyofcannabinoidrecep-tors.Ann. Rev. Pharmacol. Toxicol.(1995) 35:607–634.
  • PERTWEE RG: PharmacologyofcannabinoidCB1andCB2receptors.Pharmacol. Ther.(1997) 74:129–180.
  • ••Excellent and up-to-date revue on CBI and CB2 receptorpharmacology.
  • RAZDAN RK: Structure-activityrelationshipsincan-nabinoids.Pharmacol. Rev.(1986) 38:75–149.
  • WARD A, HOLMES B: Nabilone:apreliminaryreviewofits pharmacological properties and therapeutic use. Drugs(1985) 30:127–144.
  • MECHOULAM R, LANDER N, BREUER A et al.:Synthesisofthe individual, pharmacologically distinct enanti-omersofatetrahydrocannabinolderivative.Tetrahe-dron: Asymmetry(1990) 1:315–319.
  • DEVANE WA, BREUER A, SHESKIN T et al:Anovelprobeforthecannabinoidreceptor.J. Med. Chem.(1992) 32:2065–2069.
  • SHOWALTER VM, COMPTON DR, MARTIN BR et al.:Evaluation of binding in transfected cell line express-ing a peripheral cannabinoid receptor (CB2): identifi-cation of cannabinoid receptor subtype selective ligands.J. Pharmacol. Exp. Ther.(1996) 278:989–999.
  • ••First extensive study on the CB2 binding of known cannabi-noid ligands.
  • BIEGON A, JOSEPH AB: DevelopmentofHU-211asaneuroprotectantforischemicbraindamage.Neurol Res.(1995) 17:275–280.
  • SHOHAMI E, GALLILY R, MECHOULAM R et al.:Cytokineproduction in the brain following closed head injury: dexanabinol (HU-211) is a novel TNF-alpha inhibitor andaneffectiveneuroprotectant.J. Neuroimmunol(1997) 72:169–177.
  • BURSTEIN SH, AUDETTE CA, BREUER A et al.:Syntheticnonpsychotropic cannabinoids with potent antiin-flammatory, analgesic, and leukocyte antiadhesion ac-tivities.J. Med. Chem.(1992) 35:3135–3141.
  • BURSTEIN SH, GOLDBERG J, HUNTER SA et al.:CT3:apo-tent antiinflammatory agent with a cannabinoid tem-platestructure.1997 Symposium on the Cannabinoids.International Cannabinoid Research Society, Burlington, Vermont (1997) 67.
  • HUFFMAN JW, YU S, SHOWALTER V et al.:Synthesisandpharmacology of a very potent cannabinoid lacking a phenolic hydroxyl with high affinity for the CB2 re-ceptor.J. Med. Chem.(1996) 39:3875–3877.
  • GAREAU Y, DUFRESNE C, GALLANT M et al.:Structureac-tivity relationships of tetrahydrocannabinol ana-loguesonhumancannabinoidreceptors.Bioorg. Med. Chem. Lett.(1996) 6:189–194.
  • JOHNSON MR, MELVIN LS: Thediscoveryofnonclassi-calcannabinoidanalgesics.In: Cannabinoids as Thera-peutic Agents.Mechoulam R (Ed.), CRC Press, Boca Raton (1986) 121–145.
  • MELVIN LS, MILNE GM, JOHNSON MR et al.:Structure-activity relationships for cannabinoid receptor bind-ing and analgesic activity: studies of bicyclic cannabi-noidanalogs.Mol. Pharmacol(1993) 44:1008–1015.
  • •Discussion on the structure-activity relationships of non-classical bicyclic cannabinoids.
  • THOMAS BF, COMPTON DR, MARTIN BR et al.:Modeling the cannabinoid receptor: a three-dimensional quanti-tativestructure-activityanalysis.Mol. Pharmacol(1991) 40:656–665.
  • SCHMETZER S, GREENIDGE P, KOVAR KA et al.:Structure-activity relationships of cannabinoids: a jointCoMFAandpseudoreceptormodellingstudy.J. Comput. Aided Mol. Des.(1997) 11:278–292.
  • LAGU SG, VARONA A, CHAMBERS JD et al.:Constructionof a steric map of the binding pocket for cannabinoids atthecannabinoidreceptor.Drug Des. Discov.(1995) 12:179–192.
  • JAIN AK, RYAN JR, MCMAHON FG et al.:Evaluationofin-tramuscular levonantradol and placebo in acute post-operativepain.J. Clin. Pharmacol(1981) 21:320S–326S.
  • LITTLE PJ, COMPTON DR, JOHNSON MR et al.:Pharma-cology and stereoselectivity of structurally novel can-nabinoidsinmice.J. Pharmacol. Exp. Ther.(1988) 247:1046–1051.
  • SMITH PB, COMPTON DR, WELCH SP et al:Thepharma-cological activity of anandamide, a putative endoge-nouscannabinoid,inmice.J. Pharmacol. Exp. Ther.(1994) 270:219–227.
  • FELDER CC, NIELSEN A, BRILEY EM et al:Isolationandmeasurement of the endogenous cannabinoid recep-tor agonist anandamide, in brain and peripheral tis-suesofhumanandrat.FEBS Lett.(1996) 393:231–235.
  • MECHOULAM R, BEN-SHABAT S, HANUS L et al.:Identifi-cation of an endogenous 2-monoglyceride, present in caninegut,thatbindstocannabinoidreceptors.Bio-chem. Pharmacol.(1995) 50:83–90.
  • STELLA N, SCHWEITZER P, PIOMELLI D: Aseconden-dogenous cannabinoid that modulates long-term po-tentiation.Nature (London)(1997) 388:773–778.
  • PINTO JC, POTIE F, RICE KC et al.:Cannabinoidreceptorbinding and agonist activity of amides and esters of arachidonicacid.Mol. Pharmacol(1994) 46:516–522.
  • ADAMS IB, RYAN W, SINGER M et al.:Evaluationofcan-nabinoidreceptorbindingandin vivoactivitiesofan-andamideanalogs.J. Pharmacol. Exp. Ther.(1995) 273:1172–1181.
  • SHESKIN T, HANUS L, SLAGER J et al:Structuralrequire-ments for binding of anandamide-type compounds to thebraincannabinoidreceptor.J. Merl. Chem.(1997) 40:656–667.
  • ABADJI V, LIN S, TAHA G et al.:(R)-methanandamide:achiral novel anandamide possessing higher potency andmetabolicstability.J. Merl. Chem.(1994) 37: 1889-1893.
  • KHANOLKAR AD, ABADJI V, LIN S et al.:Headgroupana-logs of arachidonylethanolamide, the endogenous cannabinoidligand.J. Merl. Chem.(1996) 39:4515–4519.
  • RYAN WJ, BANNER WK, WILEY JL et al:Potentanan-damide analogs: the effect of changing the length and branchingoftheendpentylchain.J. Merl. Chem.(1997) 40:3617–3625.
  • SELTZMAN HH, FLEMING DN, THOMAS BF et al.:Synthe-sis and pharmacological comparison of dimethylhep-tylandpentylanalogsofanandamide.J. Merl. Chem.(1997) 40:3626–3634.
  • THOMAS BF, ADAMS IB, MASCARELLA SW et al.:Structure-activity analysis of anandamide analogs: re-lationshiptoacannabinoidpharmacophore.J. Merl. Chem.(1996) 39:471–479.
  • •Proposes an interesting alignment model between anan-damide and classical cannabinoids
  • FACCI L, DAL TOSO R, ROMANELLO S et al.:Mastcellsex-press a peripheral cannabinoid receptor with differ-ential sensitivity to anandamide and palmitoylethanolamide.Proc. Natl. Acad. Sci. USA(1995) 92:3376–3380.
  • JACK DB: Aliamides:anewapproachtothetreatmentofinflammation.Drug News Perspect.(1996) 9:93–98.
  • •Comment on the discovery and clinical use of palmitoylethanolamide.
  • BELL MR, D'AMBRA TE, KUMAR V et al.:Antinociceptive(aminoalkyfiindoles.jMed. Chem.(1991) 34:1099–1110.
  • D'AMBRA TE, ESTEP KG, BELL MR et al:Conformation-ally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists ofthecannabinoidreceptor.J. Merl. Chem.(1992) 35:124–2–135.
  • EISSENSTADT MA, BELL MR, D'AMBRA TE et al.:Aminoal-kylindoles: structure-activity relationships of novel cannabinoidmimetics.J. Merl. Chem.(1995) 38:3094–3105.
  • •The most comprehensive set of structure-activity data on aminoalkylindoles.
  • COMPTON DR, GOLD LH, WARD SJ et al.:Aminoalkylin-dole analogs: cannabimimetic activity of a class of compoundsstructurallydistinctfromA9-tetrahydr-ocannabinol.J. Pharmacol. Exp. Ther.(1992) 263:1118–1129.
  • HUFFMAN JW, DAI D, MARTIN BR et al.:Design,synthe-sis and pharmacology of cannabimimetic indoles. Bioorg. Merl. Chem. Lett.(1994) 4:563–566.
  • LAINTON JAH, HUFFMAN JW, MARTIN BR et al:1-Alkyl-3-(1-naphtoyfi pyrroles: a new class of cannabinoid. Tetrahedron Lett.(1995) 9:1401–1404.
  • SONG ZH, BONNER TI: Alysineresidueofthecannabi-noid receptor is critical for receptor recognition by severalagonistsbutnotWIN55212-2.Mol Pharmacol(1996) 49:891–896.
  • KUMAR V, ALEXANDER MD, BELL MR et al:Morpholi-noalkylindenes as antinociceptive agents: novel can-nabinoidreceptoragonists.Bioorg. Med. Chem. Lett.(1995) 5:381–386.
  • GALLANT M, DUFRESNE C, GAREAU Y et al.:Newclassofpotent ligands for the human peripheral cannabinoid receptor.Bioorg. Merl. Chem. Lett.(1996) 6:2263–2268.
  • PACHECO MA, WARD SJ, ARNOLD R et al:Aminoalkylin-doles: actions on specific G-protein-linked receptors. J. Pharmacol. Exp. Ther.(1991) 257:170–183.
  • CASIANO FM, ARNOLD R, HAYCOCK D et al.:Putativeaminoalkylindoles(AADantagonists.NIDA Res. Monogr.(1990) 105:295–296.
  • PERTWEE R, GRIFFIN G, FERNANDO S et al.:AM630,acompetitivecannabinoidreceptorantagonist.Life Sci.(1995) 56:1949–1956.
  • HOSOHATA K, QUOCK RM, HOSATA Y et al.:AM630isacompetitive cannabinoid receptor antagonist in the guineapigbrain.Life Sci.(1997) 61:115–118.
  • HOWLETT AC, BERGLUND B, MELVIN LS: Cannabinoidreceptoragonistsandantagonists.Curr. Pharm. Des.(1995) 1:343-354 © Ashley Publications Ltd. All rights reserved.Exp. Opin. Ther. Patents(1998) 8(3)
  • RINALDI-CARMONA M, BARTH F, HEAULME M et al:SR 141716A, a potent and selective antagonist of the brain cannabinoidreceptor.FEBS Lett.(1994) 350:240–244.
  • ••Disclosure and pharmacology of SR 141716, the first CBIantagonist.
  • BARTH F, RINALDI-CARMONA M: SR141716-thefirstse-lective CB1 cannabinoid receptor antagonist: an over-view.Med. Sci. Monit.(1996) 2:830–835.
  • GUEUDET C, SANTUCCI V, RINALDI-CARMONA M et al.:The CB1 cannabinoid receptor antagonist SR 141716A affectsA9dopamineneuronalactivityintherat.Neu-roReport(1995) 6:1421–1425.
  • SANTUCCI V, STORME JJ, SOUBRIE P et al.:Arousal-enhancing properties of the CB1 cannabinoid recep-tor antagonist SR 141716A in rats as assessed by elec-troencephalographic spectral and sleep-waking cycle analysis.Life Sci.(1996) 58:103–110.
  • TERRANOVA JP, STORME JJ, LAFON N et al.:Improve-ment of memory in rodents by the selective CB1 can-nabinoid receptor antagonist, SR 141716. Psychopharmacology(1996) 126:165–172.
  • ARNONE M, MARUANI J, CHAPERON F et al.:Selectivein-hibition of sucrose and ethanol intake by SR 141716, an antagonist of central cannabinoid (CB1) receptors. Psychopharmacology(1997) 132:104–106.
  • BOUABOULA M, PERRACHON S, MILLIGAN L et al:Ase-lective inverse agonist for central cannabinoid recep-tor inhibits mitogen-activated protein kinase activation stimulated by insulin or insulin-like growth factor1.J. Biol. Chem.(1997) 272:22330–22339.
  • RINALDI-CARMONA M, PIALOT F, CONGY C et al.:Char-acterisation and distribution of binding sites for [311]-SR 141716A,aselectivebrain(CB1)cannabinoidreceptorantagonistinrodentbrain.Life Sci.(1996) 58:1239–1247.
  • GATLEY SJ, LAN R, VOLKOW ND et al.:Imagingthebrainmarijuana receptor: development of a radioligand that bindstocannabinoidCB1receptorsinvivo.J. Neuro-chem.(1998) 70:417–423.
  • RINALDI-CARMONA M, BARTH F, MILLAN J et al.:SR144528, the first potent and selective antagonist of the CB2cannabinoidreceptor.J. Pharmacol Exp. Ther.(1998) 284:644–650.
  • •Disclosure and pharmacology of SR 144528, the first CB2 antagonist.
  • FELDER CC, JOYCE KE, BRILEY EM et al.:LY320135,a novel cannabinoid CB1 receptor antagonist, unmasks coupling of the CB1 receptor to stimulation of cAMP accumulation.J. Pharmacol. Exp. Ther.(1998) 284:291–297.
  • PERTWEE RG: Cannabinoidreceptorligands:clinicaland neuropharmacological considerations relevant to futuredrugdiscoveryanddevelopment.Exp. Opin. In-vest. Drugs(1996) 5:1245–1253.
  • HOLLISTER LE: Marijuanaandimmunity.J. Psychoact. Drugs(1992) 24:159–164.
  • SPECTERS, CABRAL G: Cannabinoids,immunityandre-sistancetoinfections.J. Neuroimmunol.(1996) 69:15–23.
  • DEROCQ JM, SEGUI M, MARCHAND J et al.:Cannabinoidsenhance human B-cell growth at low nanomolar con-centrations.FEBS Lett.(1995) 369:177–182.
  • SANCHEZ C, VELASCO G, GUZMAN M: Metabolicstimu-lation of mouse spleen lymphocytes by low doses of delta9-tetrahydrocannabinol.Life Sci.(1997) 19:1709–1717.
  • LAKE KD, MARTIN BR, KUNOS G et al.:Cardiovascularef-fects of anandamide in anesthetized and conscious normotensiveandhypertensiverats.Hypertension(1997) 29:1204–1210.
  • DEUTSCH DG, CHIN SA: Enzymaticsynthesisanddeg-radation of anandamide, a cannabinoid receptor ago-nist.Biochem. Pharmacol(1993) 46:791–796.
  • DI MARZO V, FONTANA A, CADAS H et al.:Formationand inactivation of endogenous cannabinoid anan-damideincentralneurons.Nature (London)(1994) 372:686–691.
  • CRAVATT BF, GIANG DK, MAYFIELD SP et al.:Molecularcharacterisation of an enzyme that degrades neuro-modulatoryfatty-acidamides.Nature (London)(1996) 384:83–87.
  • BELTRAMO M, STELLA N, CALIGNANO A etal.:Functionalrole of high-affinity anandamide transport, as re-vealedbyselectiveinhibition.Science(1997) 277:1094–1097.
  • KOUTEK B, PRESTWICH GD, HOWLETT AC et al.:Inhibi-torsofarachidonoylethanolamidehydrolysis.J. Biol. Chem.(1994) 269:22937–22940.
  • BELTRAMO M, DI TOMASO E, PIOMELLI D.: Inhibitionofanandamide hydrolysis in rat brain tissue by (E)-6-(bromomethylene)tetrahydro-3-(1-naphtaleny0-211-pyran-2-one.FEBS Lett.(1997) 403:263–267.
  • DEUTSCH DG, OMEIR R, ARREAZA F et al.:Methylarachi-donyl fluorophosphonate: a potent irreversible in-hibitorofanandamideamidase.Biochem. Pharmacol(1997) 53:255–260.
  • BRAMBLETT RD, REGGIO PH: Anexplorationofpossi-ble binding sites for cannabinoid ligands at the CB1 re-ceptor.1995 Symposium on Cannabis and the Cannabinoids.Scottsdale, International Cannabinoid Re-search Society, Burlington, Vermont (1995) 16–17.
  • SHIRE D, CALANDRA B, DELPECH et al.:Structuralfea-tures of the central cannabinoid CB1 receptor in-volved in the binding of the specific CB1 antagonist SR 141716A.J. Biol. Chem.(1996) 271:6941–6946.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.