AM-411

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AM-411
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Systematic (IUPAC) name
(6aR,10aR)-3-(1-adamantyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
Identifiers
PubChem CID 9799945
Chemical data
Formula C26H34O2
Molar mass 378.546 g/mol[[Script error: No such module "String".]]
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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.[1] It produces similar effects to other cannabinoid agonists such as analgesia, sedation and anxiolysis.[2][3]

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References

  1. ↑ 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
  2. ↑ 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
  3. ↑ 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
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