All Photos(1)
Synonym(s):
6-Methyl-2-(phenylazo)-3-pyridinol
Empirical Formula (Hill Notation):
C12H11N3O
CAS Number:
Molecular Weight:
213.24
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
新产品
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.
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
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
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