From Wikipedia, the free encyclopedia
Chemical compound
BMS-F
|
|
(S)-2-{[7-Methoxy-2-methyl-1-(2-morpholin-4-yl-ethyl)-1H-indole-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester
|
CAS Number | |
---|
PubChem
CID | |
---|
|
Formula | C27H33N3O5 |
---|
Molar mass | 479.577 g·mol−1 |
---|
3D model (
JSmol) | |
---|
CC1=C(C2=C(N1CCN3CCOCC3)C(=CC=C2)OC)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)OC
|
InChI=1S/C27H33N3O5/c1-19-24(26(31)28-22(27(32)34-3)18-20-8-5-4-6-9-20)21-10-7-11-23(33-2)25(21)30(19)13-12-29-14-16-35-17-15-29/h4-11,22H,12-18H2,1-3H3,(H,28,31)/t22-/m0/s1 Key:HQUJODHGYIPBGV-QFIPXVFZSA-N
|
BMS-F is a chemical from the
aminoalkylindole family invented by
Bristol-Myers Squibb around 1999,
[1] that acts as a potent and selective
agonist for the
cannabinoid receptor
CB2, with a
Ki of 8 nM at CB2 and 500x selectivity over the related
CB1 receptor. It has
antiinflammatory effects and inhibits release of
TNF-α.
[2]
[3]
See also
References
-
^
WO application 0158869, Leftheris K, Zhao R, Chen BC, Kiener P, Wu H, Pandit CR, Wrobleski S, Chen P, Hynes J, Longphre M, Norris DJ, Spergel S, Tokarski J, "Cannabinoid Receptor Modulators, Their Processes of Preparation, and use of Cannabinoid Receptor Modulators for Treating Respiratory and Non-Respiratory Diseases", published 16 August 2001, assigned to Bristol-Myers Squibb
-
^ Hynes Jr J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, et al. (September 2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399–2402.
doi:
10.1016/s0960-894x(02)00466-3.
PMID
12161142.
-
^ Howlett AC, Thomas BF, Huffman JW (October 2021).
"The Spicy Story of Cannabimimetic Indoles". Molecules. 26 (20): 6190.
doi:
10.3390/molecules26206190.
PMC
8538531.
PMID
34684770.
|
---|
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
CBRTooltip Cannabinoid receptor
ligands | |
---|
Endocannabinoid enhancers (inactivation inhibitors) | |
---|
Anticannabinoids (antagonists/inverse agonists/antibodies) | |
---|
|