AM-919

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AM-919
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Systematic (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
Identifiers
PubChem CID 10741414
Chemical data
Formula C27H44O4
Molar mass 432.634 g/mol[[Script error: No such module "String".]]
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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.[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 Ki of 2.2nM at CB1 and 3.4nM at CB2.[2][3]


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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
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