SML0800

Rimonabant hydrochloride

≥98% (HPLC), powder, cannabinoid type-I receptor antagonist

• Synonym(s): 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide hydrochloride, SR-141716, SR-141716A, SR141716, SR141716A
• Empirical Formula (Hill Notation): C₂₂H₂₁Cl₃N₄O · HCl
• CAS Number: 158681-13-1
• Molecular Weight: 500.25
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825601
• NACRES: NA.77

Properties

• product name: Rimonabant hydrochloride, ≥98% (HPLC)
• Assay: ≥98% (HPLC)
• form: powder
• storage condition: desiccated
• color: white to beige
• solubility: DMSO: 20 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: CC1=C(C2=CC=C(Cl)C=C2)N(C3=CC=C(Cl)C=C3Cl)N=C1C(NN4CCCCC4)=O.Cl
• InChI: 1S/C22H21Cl3N4O.ClH/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15;/h5-10,13H,2-4,11-12H2,1H3,(H,27,30);1H
• InChI key: REOYOKXLUFHOBV-UHFFFAOYSA-N
• Gene Information: human ... CNR1(1268)

Description

Application

Rimonabant hydrochloride has been used as an antagonist of cannabinoid 1 (CB1) receptor:

• to study its effects on protein synthesis in C2C12 myotubes
• to analyze its effects on human astroglia
• in combination with methanandamide (mAEA) to study its effects on murine gastric vagal afferent mechanosensitivity

Biochem/physiol Actions

Rimonabant acts as a mycobacterial membrane protein large 3 (MMPL3) inhibitor. Rimonabant hydrochloride exhibits therapeutic activity against weight reduction and smoking cessation.

Rimonabant hydrochloride (SR-141716A) is a potent and selective CB1 cannabinoid inverse agonist/antagonist with a Ki of 1.6 nM, minimal affinity for CB2, and and some GPR55 agonist activity. Rimonabant was developed as an anti-obesity drug because of its appetite suppressant activity, but was taken off the market because of side effects of depression and anxiety.

Features and Benefits

This compound is featured on the Cannabinoid Receptors and Cannabinoid Receptors pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301,H319
• Precautionary Statements: P264 - P270 - P280 - P301 + P310 - P305 + P351 + P338 - P337 + P313
• Hazard Classifications: Acute Tox. 3 Oral - Eye Irrit. 2
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable