VCHSR

VCHSR
Identifiers
	IUPAC name 5-(4-chlorophenyl)- 3-[(E)-2-cyclohexylethenyl]- 1-(2,4-dichlorophenyl)- 4-methyl- 1H-pyrazole;
ChemSpider	21378331;
Chemical and physical data
Formula	C24H23Cl3N2
Molar mass	445.811 g·mol−1
3D model (JSmol)	Interactive image;
	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

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.
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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[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.