AM-411

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AM-411
AM-411.png
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
ChemSpider 7975710 YesY
ChEMBL CHEMBL434351 YesY
Chemical data
Formula C26H34O2
Molecular mass 378.546 g/mol
  • C5C6CC4CC5(CC(C6)C4)c(cc1O3)cc(O)c1C2CC(C)=CCC2C3(C)C
  • InChI=1S/C26H34O2/c1-15-4-5-21-20(6-15)24-22(27)10-19(11-23(24)28-25(21,2)3)26-12-16-7-17(13-26)9-18(8-16)14-26/h4,10-11,16-18,20-21,27H,5-9,12-14H2,1-3H3/t16?,17?,18?,20-,21-,26?/m1/s1 YesY
  • Key:RPBMPWGKZFLMFN-OKFSJJLXSA-N YesY
  (verify)

AM-411 is an analgesic drug that 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]

See also

References

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  1. ↑ Lu D, et al. 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, et al. 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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