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SML0800

Sigma-Aldrich

Rimonabant hydrochloride

≥98% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):
C22H21Cl3N4O · HCl
CAS-Nummer:
158681-13-1
Molekulargewicht:
500.25
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329825601
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Lagerbedingungen

desiccated

Farbe

white to beige

Löslichkeit

DMSO: 20 mg/mL, clear

Lagertemp.

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

InChIKey

REOYOKXLUFHOBV-UHFFFAOYSA-N

Angaben zum Gen

human ... CNR1(1268)

Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H301 - H319

Gefahreneinstufungen

Acute Tox. 3 Oral - Eye Irrit. 2

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Sigma-Aldrich

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solid, ≥98% (HPLC)

Sigma-Aldrich

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≥97.0% (TLC), oil

Sigma-Aldrich

A0580

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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
Marc-Antoine Perrin et al.
Journal of pharmaceutical sciences, 102(7), 2311-2321 (2013-05-23)
Crystalline polymorphism occurs frequently in the solid state of active pharmaceutical ingredients, and this is problematic for the development of a suitable dose form. Rimonabant, an active pharmaceutical ingredient developed by Sanofi and discontinued because of side effects, exhibits dimorphism;
Zsuzsanna Literati-Nagy et al.
Pathology oncology research : POR, 19(3), 571-575 (2013-05-04)
Abdominal obesity is referred for as a common pathogenic root of multiple risk factors, which include insulin resistance, dyslipidemia, hypertension, and a pro-atherogenic and pro-inflammatory state. Irrespective of its psychiatric side effects, rimonabant through blocking cannabinoid-1 receptor (CB1R) induces an
Alexandre Seillier et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 38(9), 1816-1824 (2013-04-09)
The neuronal mechanisms underlying social withdrawal, one of the core negative symptoms of schizophrenia, are not well understood. Recent studies suggest an involvement of the endocannabinoid system in the pathophysiology of schizophrenia and, in particular, of negative symptoms. We used
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
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