Taranabant ((1R,2R)stereoisomer)

• CAT Number: I013751
• CAS Number: 701977-08-4
• Molecular Formula: C₂₇H₂₅ClF₃N₃O₂
• Molecular Weight: 515.95
• Purity: ≥95%
• Target: Cannabinoid Receptor
• Solubility: 10 mM in DMSO
• IUPAC Name: N-[(2R,3R)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide
• InChI: InChI=1S/C27H25ClF3N3O2/c1-17(34-25(35)26(2,3)36-24-12-9-21(16-33-24)27(29,30)31)23(14-18-7-10-22(28)11-8-18)20-6-4-5-19(13-20)15-32/h4-13,16-17,23H,14H2,1-3H3,(H,34,35)/t17-,23+/m1/s1
• InChIKey: QLYKJCMUNUWAGO-HXOBKFHXSA-N
• SMILES: C[C@H]([C@H](CC1=CC=C(C=C1)Cl)C2=CC=CC(=C2)C#N)NC(=O)C(C)(C)OC3=NC=C(C=C3)C(F)(F)F

Taranabant (the (1R,2R) stereoisomer)（Cat No.:I013751）is a selective inverse agonist of the cannabinoid receptor CB1, part of the endocannabinoid system involved in regulating appetite, metabolism, and mood. Taranabant was developed as a potential treatment for obesity and metabolic disorders by reducing appetite and body weight. It works by inhibiting the CB1 receptor, which, when activated, promotes hunger and fat accumulation. Clinical trials, however, were discontinued due to side effects such as psychiatric symptoms and cardiovascular issues. Despite its early promise, taranabant’s adverse effects limited its development as an anti-obesity drug.

Reference

[1]. William K. Hagmann, et al. Substituted amides active at the cannabinoid-1 receptor. WO 2004048317 A1.