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Chemical compound
AM-919
(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
PubChem
CID
ChemSpider
UNII
ChEMBL
Formula C 27 H 44 O 4
Molar mass 432.645 g·mol−1 3D model (
JSmol )
OCCCC3(C)C1CCC(CO)CC1c2c(O3)cc(cc2O)C(C)(C)CCCCCC
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
Y Key:PHILDZBONNKMNU-UOTIDGTBSA-N
Y
(verify)
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
Ki of 2.2 nM at CB1 and 3.4 nM at CB2 .
[2]
[3]
See also
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,
Makriyannis A , Tius MA (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 .
Phytocannabinoids (
comparison )
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