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108340

Sigma-Aldrich

3-Hydroxy-2-quinoxalinecarboxylic acid

97%

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About This Item

Empirical Formula (Hill Notation):
C9H6N2O3
CAS Number:
1204-75-7
Molecular Weight:
190.16
EC Number:
214-877-4
MDL number:
MFCD00006726
UNSPSC Code:
12352100
PubChem Substance ID:
24846662
NACRES:
NA.22

Assay

97%

mp

267-268 °C (lit.)

SMILES string

OC(=O)c1nc2ccccc2nc1O

InChI

1S/C9H6N2O3/c12-8-7(9(13)14)10-5-3-1-2-4-6(5)11-8/h1-4H,(H,11,12)(H,13,14)

InChI key

NMOWGWOAPRKWIR-UHFFFAOYSA-N

Application

3-Hydroxy-2-quinoxalinecarboxylic acid was used to study the sorption of ionizable organic compounds to an estuarine sediment. It was used in the preparation of Zinc(II)-quinoxaline complexes which was characterized by X-ray crystallography and fluorescence spectroscopy.

Biochem/physiol Actions

3-Hydroxy-2-quinoxalinecarboxylic acid is an antagonist of excitatory amino acids and possesses anticonvulsant properties. It inhibits the 22Na+ efflux produced in 22Na+-preloaded brain slices by N-methyl-D-aspartate and kainate.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

108340-5G:
108340-VAR:
108340-1G:
108340-BULK:

Certificates of Analysis (COA)

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U Erez et al.
European journal of pharmacology, 110(1), 31-39 (1985-03-26)
Various aromatic acids have been investigated as putative ligands of excitatory amino acid receptors. 3-Hydroxy-2-quinoxalinecarboxylic acid (HQC), at 1 mM, was found to antagonize the 22Na+ efflux produced in 22Na+-preloaded brain slices by N-methyl-D-aspartate and kainate. The response to glutamate
Ken-Ichi Sakai et al.
Dalton transactions (Cambridge, England : 2003), 39(8), 1989-1995 (2010-02-12)
Zinc(ii)-quinoxaline complexes, [Zn(hqxc)(2)(py)(2)] and [Zn(hqxc)(2)(DMSO)(2)] (hqxc = 3-hydroxy-2-quinoxalinecarboxylate, py = pyridine, DMSO = dimethyl sulfoxide), were prepared and characterized by X-ray crystallography and fluorescence spectroscopy. In both complexes, the zinc ion is six-coordinated by two equatorial bidentate hqxc ligands with
Serdar Badoğlu et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 101, 14-21 (2012-10-27)
The mid-IR and Raman spectra of 3-hydroxy-2-quinoxalinecarboxylic acid (3HQC) were recorded. These spectra were interpreted with the help of B3LYP/6-311++G(d,p) calculations and potential energy distribution (PED) analysis. As a result of the calculations, seven tautomers were determined among many stable
Cadmium (II) and calcium (II) complexes with N, O-bidentate ligands derived from pyrazinecarboxylic acid.
Barszcz B, et al.
Journal of Thermal Analysis and Calorimetry, 108(3), 971-978 (2012)
H Frenk et al.
Brain research, 373(1-2), 222-226 (1986-05-14)
Three compounds reportedly blocking the N-methyl-D-aspartate (NMDA) receptor, namely 2-amino-5-phosphonovalerate, gamma-D-glutamylglycine and 3-hydroxy-2-quinoxalinecarboxylic acid, were injected subdurally onto the cortex of freely moving rats. All 3 compounds effectively suppressed behavioral and electrographic seizure activity induced by strychnine, morphine and picrotoxin
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