AM-919

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 dibenzopyran and nonclassical cannabinoid families.[1]

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
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC27H44O4
Molar mass432.645 g·mol−1
3D model (JSmol)
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 Y
  • Key:PHILDZBONNKMNU-UOTIDGTBSA-N Y
  (verify)

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 Ki of 2.2 nM at CB1 and 3.4 nM at CB2.[2][3]

See also

References
  1. Pertwee R. Cannabinoids. Handbook of Experimental Pharmacology. Vol. 168. Springer. p. 269. ISBN 3-540-22565-X.
  2. Tius MA, Hill WA, Zou XL, Busch-Petersen J, Kawakami JK, Fernandez-Garcia MC, et al. (1995). "Classical/non-classical cannabinoid hybrids; stereochemical requirements for the southern hydroxyalkyl chain". Life Sciences. 56 (23–24): 2007–12. doi:10.1016/0024-3205(95)00182-6. PMID 7776825.
  3. Drake DJ, Jensen RS, Busch-Petersen J, Kawakami JK, Concepcion Fernandez-Garcia M, Fan P, Makriyannis A, Tius MA (September 1998). "Classical/nonclassical hybrid cannabinoids: southern aliphatic chain-functionalized C-6beta methyl, ethyl, and propyl analogues". Journal of Medicinal Chemistry. 41 (19): 3596–608. doi:10.1021/jm960677q. PMID 9733485.
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