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SML0800

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C22H21Cl3N4O · HCl
CAS Number:
Molecular Weight:
500.25
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Product Name

Rimonabant hydrochloride, ≥98% (HPLC)

Quality Level

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)

Application

Rimonabant hydrochloride has been used as an antagonist of cannabinoid 1 (CB1) receptor:
  • to study its effects on protein synthesis in C2C12 myotubes[1]
  • to analyze its effects on human astroglia[2]
  • in combination with methanandamide (mAEA) to study its effects on murine gastric vagal afferent mechanosensitivity[3]

Biochem/physiol Actions

Rimonabant acts as a mycobacterial membrane protein large 3 (MMPL3) inhibitor.[4] Rimonabant hydrochloride exhibits therapeutic activity against weight reduction and smoking cessation.[5]
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.
Rimonabant hydrochloride (SR-141716A) is a potent and selecvtive CB1 cannabinoid inverse agonist/antagonist with some GPR55 agonist activity and an appetite suppressant.

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

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


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A novel validated RP-HPLC method development for the estimation of rimonabant hydrochloride in bulk and tablet dosage forms
Nama S, et al.
African Journal of Pharmacy and Pharmacology, 5(2), 207-213 (2011)
Jorge Emilio Ortega et al.
European journal of pharmacology, 709(1-3), 13-19 (2013-04-09)
Current pharmacological therapies for depression, including selective serotonin reuptake inhibitors (SSRI), are far from ideal. The cannabinoid system has been implicated in control of mood and neural processing of emotional information, and the modulation of serotonin (5-HT) release in the
Wei Chen et al.
Naunyn-Schmiedeberg's archives of pharmacology, 386(8), 721-732 (2013-04-27)
Effects of cannabinoid receptor 1 (CB1R) blockade were observed by comparing 9-day and 6-week SR141716 treatments in monosodium glutamate (MSG)-induced hypometabolic and hypothalamic obesity (HO) in rats for the first time and molecular mechanisms were investigated. Compared with normal rats
Svetlana Slavic et al.
Journal of molecular medicine (Berlin, Germany), 91(7), 811-823 (2013-05-03)
The cannabinoid receptors, CB1 and CB2, are expressed in the heart, but their role under pathological conditions remains controversial. This study examined the effect of CB1 receptor blockade on cardiovascular functions after experimental MI and in experimental metabolic syndrome. MI
Erkan Kilinc et al.
The European journal of neuroscience, 55(4), 1015-1031 (2020-07-09)
Calcitonin gene-related peptide (CGRP), substance P and dural mast cells are main contributors in neurogenic inflammation underlying migraine pathophysiology. Modulation of endocannabinoid system attenuates migraine pain, but its mechanisms of action remain unclear. We investigated receptor mechanisms mediating anti-neuroinflammatory effects

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Questions

  1. Hi ! In the product information its marked that rimonabant's solubility in DMSO is "20 mg/mL, clear". Is it its maximum solubility in DMSO?

    1 answer
    1. This product is analyzed for solubility in DMSO on a lot to lot basis. The specification is: ≥ 20.0 mg/mL. Kindly review the lot specific certificate of analysis for the resulting maximum solubility of the lot received.

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