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07-SEPTEMBER-2008 03:17:44 - Ajulemic acid Ajulemic acid Systematic IUPAC name 6aR,10aR 3-1,1-dimethylheptyl-6a,7,10,10a- tetrahydro-1-hydroxy-6,6-dimethyl- 6H-Dibenzob,dpyran-9-carboxylic acid Identifiers CAS number 137945-48-3 ATC code ? PubChem 3083542 Chemical data Formula C25H36O4 Mol. mass 400.551 g/mol Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Routes ? Ajulemic acid AB-III-56, HU-239, IP-751 is a synthetic cannabinoid derivative of the non-psychoactive THC metabolite 11-nor-9-carboxy-THC which shows useful analgesic and anti-inflammatory effects without causing a subjective high.1 It is being developed for the treatment of neuropathic pain and inflammatory conditions such as arthritis.2 It does not however share the anti-emetic effects of other cannabinoids but may be useful for treating pain and chronic inflammatory conditions where nausea is not present.3 Side effects include dry mouth, tiredness and dizziness. The mechanism of action has not yet been established, but ajulemic acid may activate the CB1 receptor in a different way to psychoactive cannabinoids. The psychoactivity of ajulemic acid, comparable to that produced by tetrahydrocannabinol, the active constituent of marijuana, is indicated in several publications. 456 References ^ Burstein SH, Karst M, Schneider U, Zurier RB 2004. Ajulemic acid: A novel cannabinoid produces analgesia without a high. Life Sci. 75 12: 1513-22. doi:10.1016/j.lfs.2004.04.010. PMID 15240185. ^ Mitchell VA, Aslan S, Safaei R, Vaughan CW 2005. Effect of the cannabinoid ajulemic acid on rat models of neuropathic and inflammatory pain. Neurosci. Lett. 382 3: 231-5. doi:10.1016/j.neulet.2005.03.019. PMID 15925096. ^ Burstein S 2005. Ajulemic acid IP-751: synthesis, proof of principle, toxicity studies, and clinical trials. AAPS J 7 1: E143-8. doi:10.1208/aapsj070115. PMID 16146336. ^ Vann RE, Cook CD, Martin BR, Wiley JL 2007. Cannabimimetic properties of ajulemic acid. J. Pharmacol. Exp. Ther. 320 2: 678-86. doi:10.1124/jpet.106.111625. PMID 17105826. ^ Sumariwalla PF, Gallily R, Tchilibon S, Fride E, Mechoulam R, Feldmann M 2004. A novel synthetic, nonpsychoactive cannabinoid acid HU-320 with anti-inflammatory properties in murine collagen-induced arthritis. Arthritis Rheumatism 50 3: 985-998. doi:10.1002/art.20050. PMID 15022343. ^ Sumariwalla PF, Feldmann M, Gallily R, Mechoulam R 2004. Reply to the or. Arthritis Rheumatism 50 12: 4079-4080. doi:10.1002/art.20806. v d e Cannabinoids Plant cannabinoids CBD CBDV CBN CBG CBV CBL THC THC-C4 THCV Cannabinoid metabolites 11-Hydroxy-THC 11-nor-9-Carboxy-THC Endogenous cannabinoids Arachidonoyl ethanolamide Anandamide or AEA 2-Arachidonoylglycerol 2-AG 2-Arachidonyl glyceryl ether noladin ether Virodhamine N-arachidonoyl-dopamine NADA; Oleamide Synthetic cannabinoid agonists Classical cannabinoids Dibenzopyrans A-41988 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-938 AM-4030 AMG-1 AMG-3 AMG-36 AMG-41 Dexanabinol HU-211 DMHP Dronabinol HU-210 JWH-051 JWH-133 JWH-139 L-759,633 L-759,656 Levonantradol Nabilone Nabitan O-806 O-823 O-1057 O-1125 O-1238 O-2545 O-2694 Parahexyl THC-O-acetate THC-O-phosphate Nonclassical cannabinoids CP 47,497 CP 55,244 CP 55,940 HU-308 2-Isopropyl-5-methyl-1-2,6-dihydroxy-4-nonylphenylcyclohex-1-ene Aminoalkylindoles AM-630 AM-1241 JWH-015 JWH-018 JWH-073 JWH-081 JWH-200 L-768,242 Pravadoline WIN 55,212-2 Aminoalkylpyrroles JWH-030 JWH-147 JWH-307 Eicosanoids AM-883 Arachidonyl-2'-chloroethylamide Arachidonylcyclopropylamide Methanandamide O-585 O-689 O-1812 O-1860 O-1861 Others BAY 38-7271 BAY 59-3074 GW 842,166X JWH-171 O-2220 Endocannabinoid activity enhancers AM-404 CAY-10401 CAY-10402 N-arachidonoyl-serotonin O-1624 PF-622 PF-750 URB-597 URB-602 URB-754 Cannabinoid antagonists and inverse agonists AM-251 AM-281 AM-630 AVE-1625 BML-190 CAY-10508 CB-25 CB-52 JTE-907 LY-320,135 MK-9470 NESS-0327 O-1184 O-2050 O-2654 Rimonabant SLV-319 SR-144,528 Surinabant Taranabant VCHSR Retrieved from http://en..org/wiki/Ajulemic_acid Categories: Cannabinoids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Italiano This page was last modified on 24 June 2008, at 15:18
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