AM-411

AM-411

Drugbox
IUPAC_name = (6aR,10aR)-3-(1-adamantyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo [c] chromen-1-ol


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PubChem= 9799945
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C=26 | H=34 | O=2
molecular_weight = 378.546 g/mol
smiles = C5C6CC4CC5(CC(C6)C4)c(cc1O3)cc(O)c1C2CC(C)=CCC2C3(C)C
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AM-411 is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8THC substituted with an adamantyl group at the 3-position, demonstrating that the binding pocket for the alkyl chain at this position can accommodate significant bulk.

AM-411 is a potent and fairly selective CB1 full agonist with a Ki of 6.80nM, but is still also a moderately potent CB2 agonist with a Ki of 52.0nM. [Lu D, Meng Z, Thakur GA, Fan P, Steed J, Tartal CL, Hurst DP, Reggio PH, Deschamps JR, Parrish DA, George C, Järbe TU, Lamb RJ, Makriyannis A. Adamantyl cannabinoids: a novel class of cannabinergic ligands. "Journal of Medicinal Chemistry". 2005 Jul 14;48(14):4576-85. PMID 15999995] It produces similar effects to other cannabinoid agonists such as analgesia, sedation and anxiolysis. [Järbe TU, DiPatrizio NV, Lu D, Makriyannis A. (-)-Adamantyl-delta8-tetrahydrocannabinol (AM-411), a selective cannabinoid CB1 receptor agonist: effects on open-field behaviors and antagonism by SR-141716 in rats. "Behavioural Pharmacology". 2004 Nov;15(7):517-21. PMID 15472574] [McLaughlin PJ, Lu D, Winston KM, Thakur G, Swezey LA, Makriyannis A, Salamone JD. Behavioral effects of the novel cannabinoid full agonist AM 411. "Pharmacology, Biochemistry and Behaviour". 2005 May;81(1):78-88. PMID 15894067]

References


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