AM-938

AM-938
Identifiers
	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;
CAS Number	303113-08-8 ;
PubChem CID	10646208;
ChemSpider	8821567 ;
UNII	NPU5SWP5ZS;
Chemical and physical data
Formula	C27H40O4
Molar mass	428.613 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:FFRHKSZKZQWCOY-UOTIDGTBSA-N ;
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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 K_i of 0.3 nM at CB₂ and 1.2 nM at CB₁, a selectivity of around four-fold.^[2]^[3]

References

^ Pertwee R. Cannabinoids. Handbook of Experimental Pharmacology. Vol. 168. Springer. p. 269. ISBN 3-540-22565-X.
^ 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.
^ 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.

[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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[2]

[3]

See also

References