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AM-938

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
AM-938
Identifiers
  • (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
CAS Number
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC27H40O4
Molar mass428.613 g·mol−1
3D model (JSmol)
  • Oc2cc(cc1O[C@@](C#CCO)([C@@H]3CC[C@H](C[C@H]3c12)CO)C)C(C)(C)CCCCCC
  • InChI=1S/C27H40O4/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,5-8,10-12,14-15,18H2,1-4H3/t19-,21-,22-,27+/m1/s1 ☒N
  • Key:FFRHKSZKZQWCOY-UOTIDGTBSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

AM-938 (part of theAM cannabinoid series) is ananalgesic drug which is acannabinoid receptor agonist. It is a derivative ofHU-210 which has been substituted with a 6β-(3-hydroxyprop-1-ynyl) group. This adds a "southern"aliphatichydroxyl group to the molecule as seen in theCP-series of nonclassical cannabinoid drugs, and so AM-938 represents a hybrid structure between theclassical andnonclassicalcannabinoid families,[1] with the 6-hydroxyalkyl chain rigidified with atriple bond. This gives AM-938 a greater degree of selectivity, so while it is still a potent agonist at bothCB1 andCB2, it is reasonably selective for CB2, with aKi of 0.3 nM at CB2 and 1.2 nM at CB1, a selectivity of around four-fold.[2][3]

See also

[edit]
  • AM-4030 - double bond instead of a triple bond
  • AM-919 - saturated rather than a triple bond
  • HU-243 - "southern" side chain replaced by methyl unit

References

[edit]
  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, et al. (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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