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G8173

Sigma-Aldrich

GW833972A

≥98% (HPLC), powder

Synonym(s):

2-[(3-chlorophenyl)amino]-N-(4-pyridinylmethyl)-4-(trifluoromethyl)-5-Pyrimidinecarboxamide hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H13ClF3N5O · HCl
CAS Number:
1092502-33-4
Molecular Weight:
444.24
MDL number:
MFCD18452844
UNSPSC Code:
12352200
PubChem Substance ID:
329799976
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

desiccated

color

off-white to light brown

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

Cl.FC(F)(F)c1nc(Nc2cccc(Cl)c2)ncc1C(=O)NCc3ccncc3

InChI

1S/C18H13ClF3N5O.ClH/c19-12-2-1-3-13(8-12)26-17-25-10-14(15(27-17)18(20,21)22)16(28)24-9-11-4-6-23-7-5-11;/h1-8,10H,9H2,(H,24,28)(H,25,26,27);1H

InChI key

UBHSVFAUAKIVKL-UHFFFAOYSA-N

Application

GW833972A, a selective CB2 cannabinoid receptor agonist, may be used separately or in comparison to other cannabinoid receptor agonist and antagonists to differentiate and characterize the CB2 cannabinoid receptor. GW833972A may be used to help verify that an observed physiological response is cannabinoid receptor CB2-dependent.

Biochem/physiol Actions

GW833972A is a CB2 cannabinoid receptor agonist with 1000-fold selectivity relative to CB1. It is, however, 15-fold less potent than HU210 for CB2 (Ki 7.8 vs. 0.52 nM). The antitumor compound oxaliplatin induces marked hypersensitivity to cold, heat, and chemical pain stimuli (to the point where oxaliplatin therapy has to be discontinued). The hyperalgesia effect is almost completely blocked by pretreatment with GW833972A.
The compound was used to determine the role of CB2 in airway sensory nerve function.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335,H413

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Joanna M Wardlaw et al.
Neurology, 82(15), 1331-1338 (2014-03-14)
To determine the magnitude of potentially causal relationships among vascular risk factors (VRFs), large-artery atheromatous disease (LAD), and cerebral white matter hyperintensities (WMH) in 2 prospective cohorts. We assessed VRFs (history and measured variables), LAD (in carotid, coronary, and leg
Agnès Hartemann et al.
The lancet. Diabetes & endocrinology, 1(4), 295-305 (2014-03-14)
An improper balance of regulatory/effector T (Treg/Teff) cells is central to the development of autoimmune diseases, including type 1 diabetes. We previously showed that low-dose interleukin 2 (IL2) induced Treg cell expansion and activation and clinical improvement in patients with
Michael Mannstadt et al.
The lancet. Diabetes & endocrinology, 1(4), 275-283 (2014-03-14)
Hypoparathyroidism results in impaired mineral homoeostasis, including hypocalcaemia and hyperphosphataemia. Treatment with high-dose oral calcium and active vitamin D does not provide adequate or consistent control of biochemical indices and can lead to serious long-term complications. We aimed to test
Chen Stein-Zamir et al.
The Pediatric infectious disease journal, 33(7), 777-779 (2014-03-14)
We evaluated the outcome of invasive meningococcal disease in children <15 years of age (n = 181). Neisseria meningitidis serogroup B comprised 78% of bacterial isolates. Case fatality rate was 11.6%. In follow-up interviews (115/160 survivors, 72%), at least 1
Vittorio Demicheli et al.
The Cochrane database of systematic reviews, 3(3), CD001269-CD001269 (2014-03-14)
Different types of influenza vaccines are currently produced worldwide. Vaccination of pregnant women is recommended internationally, while healthy adults are targeted in North America. To identify, retrieve and assess all studies evaluating the effects (efficacy, effectiveness and harm) of vaccines
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