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SML0800

Sigma-Aldrich

Rimonabant hydrochloride

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

Sinônimo(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

Fórmula empírica (Notação de Hill):
C22H21Cl3N4O · HCl
Número CAS:
158681-13-1
Peso molecular:
500.25
Código UNSPSC:
12352200
ID de substância PubChem:
329825601
NACRES:
NA.77

product name

Rimonabant hydrochloride, ≥98% (HPLC)

Ensaio

≥98% (HPLC)

forma

powder

condição de armazenamento

desiccated

cor

white to beige

solubilidade

DMSO: 20 mg/mL, clear

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

REOYOKXLUFHOBV-UHFFFAOYSA-N

Informações sobre genes

human ... CNR1(1268)

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Pictogramas

Skull and crossbones
GHS06

Palavra indicadora

Danger

Frases de perigo

H301,H319

Classificações de perigo

Acute Tox. 3 Oral - Eye Irrit. 2

Código de classe de armazenamento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Sigma-Aldrich

A0580

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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
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)
Lubin Chen et al.
Pain, 161(6), 1350-1360 (2020-01-25)
Sodium channel Nav1.7, encoded by the SCN9A gene, is a well-validated target that plays a key role in controlling pain sensation. Loss-of-function mutations of Nav1.7 can cause a syndrome of profound congenital insensitivity to pain in humans. Better understanding of
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
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
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