AM-2389

AM-2389

Identifiers
IUPAC name (6aR,9R,10aR)-3-(1-hexylcyclobut-1-yl)-6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-6H-dibenzo[b,d]pyran-1,9 diol
CAS Number	1256842-49-5 N
PubChem CID	49783410
ChemSpider	26333264 Y
UNII	GGT8LM8A2O
CompTox Dashboard (EPA)	DTXSID70678538
Chemical and physical data
Formula	C25H38O3
Molar mass	386.576 g·mol−1
3D model (JSmol)	Interactive image
SMILES OC1=C([C@@H]2C[C@@H](CC[C@H]2C(C)(O3)C)O)C3=CC(C4(CCC4)CCCCCC)=C1
InChI InChI=1S/C25H38O3/c1-4-5-6-7-11-25(12-8-13-25)17-14-21(27)23-19-16-18(26)9-10-20(19)24(2,3)28-22(23)15-17/h14-15,18-20,26-27H,4-13,16H2,1-3H3/t18-,19-,20-/m1/s1 Y Key:CSXKNESDVLECTJ-VAMGGRTRSA-N Y
NY (what is this?)

AM-2389 is a classical cannabinoid derivative which acts as a potent and reasonably selective agonist for the CB₁ receptor, with a K_i of 0.16 nM, and 26× selectivity over the related CB₂ receptor. It has high potency in animal tests of cannabinoid activity, and a medium duration of action.^[1][2] Replacing the 1',1'-dimethyl substitution of the dimethylheptyl side chain of classical cannabinoids with cyclopropyl or cyclopentyl results in higher potency than cyclobutyl, but only the cyclobutyl derivatives show selectivity for CB₁ over CB₂.^[3] High selectivity for CB₁ over CB₂ is difficult to achieve (cf. AM-906, AM-1235), as almost all commonly used CB₁ agonists have similar or greater affinity for CB₂ than CB₁, and the only truly highly selective CB₁ agonists known as of 2012 are eicosanoid derivatives such as O-1812.^{[citation needed]}

See also

• HHC
• AMG-36
• AMG-41

References