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S9186

Sigma-Aldrich

SIB 1757

≥99% (HPLC), crystalline

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H11N3O
CAS Number:
31993-01-8
Molecular Weight:
213.24
MDL number:
MFCD00506102
UNSPSC Code:
12352202
PubChem Substance ID:
24278717
NACRES:
NA.77

Quality Level

100

assay

≥99% (HPLC)

form

crystalline

color

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+

InChI key

LOCPVWIREQIGNQ-CCEZHUSRSA-N

Gene Information

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

Application

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

Biochem/physiol Actions

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

Features and Benefits

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (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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