AM-919

AM-919
Identifiers
	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;
CAS Number	164228-46-0 ;
PubChem CID	10741414;
ChemSpider	8916745 ;
ChEMBL	ChEMBL121118 ;
Chemical and physical data
Formula	C27H44O4
Molar mass	432.645 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OCCCC3(C)C1CCC(CO)CC1c2c(O3)cc(cc2O)C(C)(C)CCCCCC;
	InChI InChI=1S/C27H44O4/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,5-15,18H2,1-4H3/t19-,21-,22-,27+/m1/s1 ; Key:PHILDZBONNKMNU-UOTIDGTBSA-N ;
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AM-919 (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-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 dibenzopyran 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 K_i of 2.2 nM at CB₁ and 3.4 nM at CB₂.[2][3]

References

Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology. 168. Springer. p. 269. ISBN 3-540-22565-X.
Tius, M. A.; Hill, W. A.; Zou, X. L.; Busch-Petersen, J.; Kawakami, J. K.; Fernandez-Garcia, M. C.; Drake, D. J.; Abadji, V.; Makriyannis, A. (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, D. J.; Jensen, R. S.; Busch-Petersen, J.; Kawakami, J. K.; Concepcion Fernandez-Garcia, M.; Fan, P.; Makriyannis, A.; Tius, M. A. (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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[1] Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology. 168. Springer. p. 269. ISBN 3-540-22565-X.

[2] Tius, M. A.; Hill, W. A.; Zou, X. L.; Busch-Petersen, J.; Kawakami, J. K.; Fernandez-Garcia, M. C.; Drake, D. J.; Abadji, V.; Makriyannis, A. (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, D. J.; Jensen, R. S.; Busch-Petersen, J.; Kawakami, J. K.; Concepcion Fernandez-Garcia, M.; Fan, P.; Makriyannis, A.; Tius, M. A. (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.

AM-919

See also

References