SML0800

Rimonabant hydrochloride

Name: Rimonabant hydrochloride
Brand: SIGMA

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

Sinónimos:

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 (notación de Hill):

C₂₂H₂₁Cl₃N₄O · HCl

Número CAS:

158681-13-1

Peso molecular:

500.25

UNSPSC Code:

12352200

PubChem Substance ID:

329825601

NACRES:

NA.77

Nombre del producto

Rimonabant hydrochloride, ≥98% (HPLC)

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

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

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.

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

GHS06

signalword

Danger

hcodes

H301,H319

pcodes

P264 - P270 - P280 - P301 + P310 - P305 + P351 + P338 - P337 + P313

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2

Clase de almacenamiento

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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Rehabilitating rimonabant.

Friedrich C Luft

Journal of molecular medicine (Berlin, Germany), 91(7), 777-779 (2013-04-18)

Additive effect of rimonabant and citalopram on extracellular serotonin levels monitored with in vivo microdialysis in rat brain.

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

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)

Effects of CB1 receptor blockade on monosodium glutamate induced hypometabolic and hypothalamic obesity in rats.

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

Mitochondrial biogenesis is altered in HIV+ brains exposed to ART: Implications for therapeutic targeting of astroglia.

Mary K Swinton et al.

Neurobiology of disease, 130, 104502-104502 (2019-06-27)

The neuropathogenesis of HIV associated neurocognitive disorders (HAND) involves disruption of mitochondrial homeostasis and increased neuroinflammation. However, it is unknown if alterations in mitochondrial biogenesis in the brain underlie the neuropathogenesis of HAND. In this study, neuropathological and molecular analyses

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