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14-September-2008 18:38:50 - AMG-3 Systematic IUPAC name 6aR,10aR-3-2-hexyl-1,3-dithiolan-2-yl-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzocchromen-1-ol Identifiers CAS number ? ATC code ? PubChem 10002952 Chemical data Formula C25H36O2S2 Mol. mass 432.681 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Routes ? AMG-3 is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8THC substituted with a dithiolane group on the 3-position side chain.1 AMG-3 is a potent agonist at both CB1 and CB2 receptors with a Ki of 0.32nM at CB1 and 0.52nM at CB2,23 and its particularly high binding affinity has led to it being used as a template for further structural development of novel cannabinoid drugs.4 It has sedative and analgesic effects, with analgesia lasting for up to 24 hours after administration.5 References ^ Mavromoustakos T, Theodoropoulou E, Zervou M, Kourouli T, Papahatjis D. Structure elucidation and conformational properties of synthetic cannabinoids --2-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-1-hydroxy-6H-dibenzob,dpyranyl-2-hexyl-1,3-dithiolane and its methylated analog. Journal of Pharmaceutical and Biomedical Analysis. 1999 Jan;186:947-56. PMID 9925329 ^ Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A. Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols. Journal of Medicinal Chemistry. 1998 Mar 26;417:1195-200. PMID 9544219 ^ Papahatjis DP, Nikas SP, Kourouli T, Chari R, Xu W, Pertwee RG, Makriyannis A. Pharmacophoric requirements for the cannabinoid side chain. Probing the cannabinoid receptor subsite at C1'. Journal of Medicinal Chemistry. 2003 Jul 17;4615:3221-9. PMID 12852753 ^ Durdagi S, Papadopoulos MG, Papahatjis DP, Mavromoustakos T. Combined 3D QSAR and molecular docking studies to reveal novel cannabinoid ligands with optimum binding activity. Bioorganic and Medicinal Chemistry Letters. 2007 Dec 15;1724:6754-63. PMID 17980589 ^ Antoniou K, Galanopoulos A, Vlachou S, Kourouli T, Nahmias V, Thermos K, Panagis G, Daifoti Z, Marselos M, Papahatjis D, Spyraki C. Behavioral pharmacological properties of a novel cannabinoid 1',1'-dithiolane delta8-THC analog, AMG-3. Behavioural Pharmacology. 2005 Sep;165-6:499-510. PMID 16148456 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 Tablets This pharmacology-related article is a stub. Retrieved from http://en..org/wiki/AMG-3 Categories: Cannabinoids | Pharmacology stubs 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 This page was last modified on 9 May 2008, at 09:30
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