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AM-411

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
AM-411
Identifiers
  • (6aR,10aR)-3-(1-Adamantyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC26H34O2
Molar mass378.556 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:RPBMPWGKZFLMFN-OKFSJJLXSA-N checkY
  (verify)

AM-411 (part of theAM cannabinoid series) is ananalgesic drug that is acannabinoidagonist. It is a derivative of Δ8-THC substituted with anadamantyl group at the 3-position, demonstrating that the binding pocket for thealkyl chain at this position can accommodate significant bulk.

AM-411 is a potent and fairly selective CB1 full agonist with aKi 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 asanalgesia,sedation, andanxiolysis.[2][3]

See also

[edit]

References

[edit]
  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.
Phytocannabinoids
(comparison)
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AllostericCBRTooltip Cannabinoid receptorligands
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