VCHSR

VCHSR
Identifiers
IUPAC name
  • 5-(4-chlorophenyl)- 3-[(E)-2-cyclohexylethenyl]- 1-(2,4-dichlorophenyl)- 4-methyl- 1H-pyrazole
ChemSpider
Chemical and physical data
FormulaC24H23Cl3N2
Molar mass445.811 g·mol−1
3D model (JSmol)
SMILES
  • C4CCCCC4C=Cc(c(C)c1-c(cc3)ccc3Cl)nn1-c2ccc(Cl)cc2Cl
InChI
  • InChI=1S/C24H23Cl3N2/c1-16-22(13-7-17-5-3-2-4-6-17)28-29(23-14-12-20(26)15-21(23)27)24(16)18-8-10-19(25)11-9-18/h7-15,17H,2-6H2,1H3/b13-7+
  • Key:UMOLSRBHNLXWGD-NTUHNPAUSA-N
  (verify)

VCHSR is a drug used in scientific research which acts as a selective antagonist of the cannabinoid receptor CB1. It is derived from the widely used CB1 antagonist rimonabant, and has similar potency and selectivity for the CB1 receptor, but has been modified to remove the hydrogen bonding capability in the C-3 substituent region, which removes the inverse agonist effect that rimonabant produces at high doses, so that VCHSR instead acts as a neutral antagonist, blocking the receptor but producing no physiological effect of its own.[1][2]

References

  1. ↑ Hurst DP, Lynch DL, Barnett-Norris J, Hyatt SM, Seltzman HH, Zhong M, et al. (December 2002). "N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A) interaction with LYS 3.28(192) is crucial for its inverse agonism at the cannabinoid CB1 receptor". Molecular Pharmacology. 62 (6): 1274–87. doi:10.1124/mol.62.6.1274. PMID 12435794.
  2. ↑ Hurst D, Umejiego U, Lynch D, Seltzman H, Hyatt S, Roche M, et al. (October 2006). "Biarylpyrazole inverse agonists at the cannabinoid CB1 receptor: importance of the C-3 carboxamide oxygen/lysine3.28(192) interaction". Journal of Medicinal Chemistry. 49 (20): 5969–87. doi:10.1021/jm060446b. PMID 17004712.
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