BMS-F

BMS-F
Identifiers
	IUPAC name (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	354569-07-6 ;
PubChem CID	10227614;
Chemical and physical data
Formula	C27H33N3O5
Molar mass	479.577 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C2=C(N1CCN3CCOCC3)C(=CC=C2)OC)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)OC;
	InChI 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 K_i 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]

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.