From Wikipedia, the free encyclopedia
Chemical compound
AM-938
(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
PubChem
CID
ChemSpider
UNII
Formula C 27 H 40 O 4
Molar mass 428.613 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
N Y
(what is this?)
(verify)
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 0.3 nM at CB2 and 1.2 nM at CB1 , a selectivity of around four-fold.
[2]
[3]
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
^ 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 .
Phytocannabinoids (
comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols
Eicosanoids
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)