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S9186

Sigma-Aldrich

SIB 1757

≥99% (HPLC), crystalline

Synonym(e):

6-Methyl-2-(phenylazo)-3-pyridinol

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About This Item

Empirische Formel (Hill-System):
C12H11N3O
CAS-Nummer:
31993-01-8
Molekulargewicht:
213.24
MDL-Nummer:
MFCD00506102
UNSPSC-Code:
12352202
PubChem Substanz-ID:
24278717
NACRES:
NA.77

Assay

≥99% (HPLC)

Form

crystalline

Farbe

red

SMILES String

Cc1ccc(O)c(\N=N\c2ccccc2)n1

InChI

1S/C12H11N3O/c1-9-7-8-11(16)12(13-9)15-14-10-5-3-2-4-6-10/h2-8,16H,1H3/b15-14+

InChIKey

LOCPVWIREQIGNQ-CCEZHUSRSA-N

Angaben zum Gen

human ... GRM1(2911) , GRM5(2915)

Anwendung

SIB 1757 may be used in mGluR5 metabotropic glutamate receptor-mediated cell signaling studies.

Biochem./physiol. Wirkung

SIB 1757 is a highly selective mGluR5 metabotropic glutamate receptor antagonist. It non-competitively inhibits glutamate-induced increase in Ca2+ at human metabotropic glutamate receptor 1 (hmGluR1).1 Inhibition of mGlu5 receptor renders protection to neurons2 against methamphetamine-induced oxidative damage.3

Leistungsmerkmale und Vorteile

This compound is featured on the Glutamate Receptors (G Protein Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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V Bruno et al.
Neuropharmacology, 39(12), 2223-2230 (2000-09-07)
We have used potent and selective non-competitive antagonists of metabotropic glutamate receptor subtype 5 (mGlu5) -- 2-methyl-6-phenylethynylpyridine (MPEP), [6-methyl-2-(phenylazo)-3-pyridinol] (SIB-1757) and [(E)-2-methyl-6-(2-phenylethenyl)pyridine] (SIB-1893) - to examine whether endogenous activation of this particular metabotropic glutamate receptor subtype contributes to neuronal degeneration.
Giuseppe Battaglia et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 22(6), 2135-2141 (2002-03-16)
Methamphetamine (MA), a widely used drug of abuse, produces oxidative damage of nigrostriatal dopaminergic terminals. We examined the effect of subtype-selective ligands of metabotropic glutamate (mGlu) receptors on MA neurotoxicity in mice. MA (5 mg/kg, i.p.; injected three times, every
M A Varney et al.
The Journal of pharmacology and experimental therapeutics, 290(1), 170-181 (1999-06-25)
Cell lines expressing the human metabotropic glutamate receptor subtype 5a (hmGluR5a) and hmGluR1b were used as targets in an automated high-throughput screening (HTS) system that measures changes in intracellular Ca2+ ([Ca2+]i) using fluorescence detection. This functional screen was used to

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