AM-938

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AM-938
240px
Systematic (IUPAC) name
(6S,6aR,9R,10aR)-9-(hydroxymethyl)-6-(3-hydroxyprop-1-ynyl)-6-

methyl-3-(2-methyloctan-2-yl)-6a,7,8,

9,10,10a-hexahydrobenzo[c]chromen-1-ol
Identifiers
PubChem CID 10646208
Chemical data
Formula C27H40O4
Molar mass 428.603 g/mol[[Script error: No such module "String".]]
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AM-938 is an analgesic drug which is a cannabinoid agonist. It is a derivative of HU-210 which has been substituted with a 6β-(3-hydroxyprop-1-ynyl) group. This adds a "southern" aliphatic hydroxyl group to the molecule as seen in the CP- series of nonclassical cannabinoid drugs, and so AM-938 represents a hybrid structure between the classical and nonclassical cannabinoid families,[1] with the 6-hydroxyalkyl chain rigidified with a triple bond. This gives AM-938 a greater degree of selectivity, so while it is still a potent agonist at both CB1 and CB2, it is reasonably selective for CB2, with a Ki of 0.3nM at CB2 vs 1.2nM at CB1, a selectivity of around 4x.[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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