Skip to Content
Merck

Key Documents

View All Documentation

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

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
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Rimonabant hydrochloride, ≥98% (HPLC)

Quality Level

100

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

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
GHS06

signalword

Danger

hcodes

H301,H319

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2

Storage Class

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000531201
0000531201
0000437884
0000437884
0000146775

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Fabricio H Do Monte et al.
Behavioural brain research, 250, 23-27 (2013-05-07)
Previous studies have implicated cannabinoids in extinction of conditioned fear. We have recently showed that intraventricular infusion of the phytocannabinoid cannabidiol (CBD) facilitates fear extinction, but the brain regions underlying this effect remained unknown. Here we demonstrate that repeated microinjections
Rehabilitating rimonabant.
Friedrich C Luft
Journal of molecular medicine (Berlin, Germany), 91(7), 777-779 (2013-04-18)
View All Related Papers