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Merck

SML0800

Sigma-Aldrich

Rimonabant hydrochloride

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

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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5 MG
CHF 96.70
25 MG
CHF 392.00

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5 MG
CHF 96.70
25 MG
CHF 392.00

About This Item

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

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Produktbezeichnung

Rimonabant hydrochloride, ≥98% (HPLC)

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[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. Wirkung

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.

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

Signalwort

Danger

H-Sätze

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


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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
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)
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;
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
Francisco Alen et al.
PloS one, 8(4), e60918-e60918 (2013-04-09)
Ghrelin is an endogenous regulator of energy homeostasis synthesized by the stomach to stimulate appetite and positive energy balance. Similarly, the endocannabinoid system is part of our internal machinery controlling food intake and energy expenditure. Both peripheral and central mechanisms

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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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