AM-919

Drugbox
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

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PubChem= 10741414
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C=27 | H=44 | O=4
molecular_weight = 432.634 g/mol
smiles = OCCCC3(C)C1CCC(CO)CC1c2c(O3)cc(cc2O)C(C)(C)CCCCCC
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AM-919 is an analgesic drug which is a cannabinoid 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. [Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168, p 269. Springer. ISBN 3-540-22565-X]

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 2.2nM at CB₁ and 3.4nM at CB₂. [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] [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]

References