AM-938

AM-938 (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-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 and 1.2nM at CB1, a selectivity of around 4x.[2][3]

AM-938
Identifiers
IUPAC name
  • (6S,6aR,9R,10aR)-9-(hydroxymethyl)-6-(3-hydroxyprop-1-ynyl)-6-
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC27H40O4
Molar mass428.613 g·mol−1
3D model (JSmol)
SMILES
  • Oc2cc(cc1O[C@@](C#CCO)([C@@H]3CC[C@H](C[C@H]3c12)CO)C)C(C)(C)CCCCCC
InChI
  • 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
 NY (what is this?)  (verify)

See also
  • 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
  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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