AM-919

AM-919

Identifiers
IUPAC name (6S,6aR,9R,10aR)-9-(hydroxymethyl)-6-(3-hydroxypropyl)-6-methyl-3-(2-methyloctan-2-yl)-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number	164228-46-0
PubChem (CID)	10741414
ChemSpider	8916745
ChEMBL	CHEMBL121118
Chemical and physical data
Formula	C27H44O4
Molar mass	432.634 g/mol
3D model (Jmol)	Interactive image
SMILES OCCCC3(C)C1CCC(CO)CC1c2c(O3)cc(cc2O)C(C)(C)CCCCCC
InChI InChI=1S/C27H44O4/c1-5-6-7-8-12-26(2,3)20-16-23(30)25-21-15-19(18-29)10-11-22(21)27(4,13-9-14-28)31-24(25)17-20/h16-17,19,21-22,28-30H,5-15,18H2,1-4H3/t19-,21-,22-,27+/m1/s1 Key:PHILDZBONNKMNU-UOTIDGTBSA-N
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AM-919 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid receptor agonist. It is a derivative of HU-210 which has been substituted with a 6β-(3-hydroxypropyl) group. This adds a "southern" aliphatic hydroxyl group to the molecule as seen in the CP-series of nonclassical cannabinoid drugs, and so AM-919 represents a hybrid structure between the classical and nonclassical cannabinoid families.^[1]

AM-919 is somewhat less potent than HU-210 itself, but is still a potent agonist at both CB₁ and CB₂ with moderate selectivity for CB₁, with a K_i of 2.2nM at CB₁ and 3.4nM at CB₂.^[2][3]

See also

• AM-4030

References

1. Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168, p 269. Springer. ISBN 3-540-22565-X
2. Tius MA, Hill WA, Zou XL, Busch-Petersen J, Kawakami JK, Fernandez-Garcia MC, Drake DJ, Abadji V, Makriyannis A. Classical/non-classical cannabinoid hybrids; stereochemical requirements for the southern hydroxyalkyl chain. Life Sciences. 1995;56(23-24):2007-12. PMID 7776825
3. Drake DJ, Jensen RS, Busch-Petersen J, Kawakami JK, Concepcion Fernandez-Garcia M, Fan P, Makriyannis A, Tius MA. Classical/nonclassical hybrid cannabinoids: southern aliphatic chain-functionalized C-6beta methyl, ethyl, and propyl analogues. Journal of Medicinal Chemistry. 1998 Sep 10;41(19):3596-608. PMID 9733485