VCHSR

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VCHSR
Systematic (IUPAC) name
5-(4- chlorophenyl)-3-[(E)-2-cyclohexylethenyl]-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole
Identifiers
CAS number  ?
ATC code  ?
PubChem  ?
Chemical data
Formula C24H23Cl3N2 
Mol. mass 445.811
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

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Legal status
Routes  ?

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 C3 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, Song Z-H, Nie J, Lewis D, Reggio PH (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. 2002 Dec;62(6):1274-87. PMID 12435794
  2. ↑ Hurst D, Umejiego U, Lynch D, Seltzman H, Hyatt S, Roche M, McAllister S, Fleischer D, Kapur A, Abood M, Shi S, Jones J, Lewis D, Reggio P. Biarylpyrazole inverse agonists at the cannabinoid CB1 receptor: importance of the C-3 carboxamide oxygen/lysine3.28(192) interaction. Journal of Medicinal Chemistry. 2006 Oct 5;49(20):5969-87. PMID 17004712



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Cannabinoid metabolites11-Hydroxy-THC • 11-nor-9-Carboxy-THC
Endogenous cannabinoidsArachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA)
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Aminoalkylpyrroles

JWH-030 • JWH-147 • JWH-307

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Cannabinoid antagonists and inverse agonists

AM-251 • AM-281 • AM-630 • BML-190 • JTE-907 • LY-320,135 • NESS-0327 • O-1184 • O-2050 • O-2654 • Rimonabant • SLV-319 • SR-144,528 • Surinabant • Taranabant • VCHSR

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