AM-411

AM-411 (part of the AM cannabinoid series) is an analgesic drug that is a cannabinoid agonist. It is a derivative of Δ8-THC 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
Identifiers
IUPAC name
  • (6aR,10aR)-3-(1-Adamantyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC26H34O2
Molar mass378.556 g·mol−1
3D model (JSmol)
SMILES
  • C5C6CC4CC5(CC(C6)C4)c(cc1O3)cc(O)c1C2CC(C)=CCC2C3(C)C
InChI
  • 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 Y
  • Key:RPBMPWGKZFLMFN-OKFSJJLXSA-N Y
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AM-411 is a potent and fairly selective CB1 full agonist with a Ki of 6.80 nM, but is still also a moderately potent CB2 agonist with a Ki of 52.0 nM.[1] It produces similar effects to other cannabinoid agonists such as analgesia, sedation, and anxiolysis.[2][3]

See also

References
  1. Lu D, Meng Z, Thakur GA, Fan P, Steed J, Tartal CL, et al. (July 2005). "Adamantyl cannabinoids: a novel class of cannabinergic ligands". Journal of Medicinal Chemistry. 48 (14): 4576–85. doi:10.1021/jm058175c. PMID 15999995.
  2. Järbe TU, DiPatrizio NV, Lu D, Makriyannis A (November 2004). "(-)-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. 15 (7): 517–21. doi:10.1097/00008877-200411000-00008. PMID 15472574. S2CID 23889056.
  3. McLaughlin PJ, Lu D, Winston KM, Thakur G, Swezey LA, Makriyannis A, Salamone JD (May 2005). "Behavioral effects of the novel cannabinoid full agonist AM 411". Pharmacology, Biochemistry, and Behavior. 81 (1): 78–88. doi:10.1016/j.pbb.2005.02.005. PMID 15894067. S2CID 806517.
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