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Merck

K3375

Sigma-Aldrich

Kynurenic acid

≥98% (HPLC), powder, NMDA receptor antagonist

Synonym(s):

4-Hydroxyquinoline-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H7NO3
CAS Number:
492-27-3
Molecular Weight:
189.17
Beilstein:
147451
EC Number:
207-751-5
MDL number:
MFCD00006753
UNSPSC Code:
12352106
PubChem Substance ID:
24277986
NACRES:
NA.77

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Product Name

Kynurenic acid, ≥98%

Quality Level

200

Assay

≥98%

form

powder

mp

275 °C (dec.) (lit.)

SMILES string

OC(=O)c1cc(O)c2ccccc2n1

InChI

1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)

InChI key

HCZHHEIFKROPDY-UHFFFAOYSA-N

Gene Information

human ... CHRNA1(1134), CHRNA10(57053), CHRNA2(1135), CHRNA3(1136), CHRNA4(1137), CHRNA5(1138), CHRNA6(8973), CHRNA7(1139), CHRNA9(55584), CHRNB1(1140), CHRNB2(1141), CHRNB3(1142), CHRNB4(1143), GRIA3(2892), GRIA4(2893), GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIK5(2901), GUCA2A(2980), GUCA2B(2981), NGFR(4804), SLC23A2(9962)
rat ... Gria1(50592), Grik1(29559), Grin2a(24409)

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Application

Kynurenic acid has been used as a constituent in dissection saline solution for embryonic cerebral cortical cells and human primary astrocytes. It has also been used as a medium supplement for murine intestinal epithelial cell line, MODE-K and induced pluripotent stem cell (iPSC)-derived neurons cells.

Biochem/physiol Actions

Kynurenic acid (KynA) is a non-selective antagonist of N-methyl-d-aspartate (NMDA), α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) and kainate receptors. It blocks kainic acid neurotoxicity. Kynurenic acid also blocks nicotinic acetylcholine receptors. It is a by-product of tryptophan catabolic pathway. Kynurenic acid is a neuromodulator and controls the levels of glutamate, dopamine, acetylcholine and α-aminobutyric acid (GABA). KynA controls neuroendocrine functions and altered levels of KynA is a potential marker in depression, schizophrenia Alzheimer′s and Huntington′s diseases. Normal levels of KynA in the brain is crucial for the cognitive function.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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

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Certificates of Analysis (COA)

Lot/Batch Number
SLCM2227
SLCL5026
SLCG9768
SLCD1287
SLCD0834

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Kynurenic acid is a nutritional cue that enables behavioral plasticity
Lemieux GA, et al.
Cell, 160(1), 119-131 (2015)
Role of kynurenines in the neurotoxic actions of kainic acid
Behan WMH and Stone TW
British Journal of Pharmacology, 129(8), 1764-1770 (2000)
Inhibiting Stearoyl-CoA Desaturase Ameliorates alpha-Synuclein Cytotoxicity
Vincent BM, et al.
Cell Reports, 25(10), 2742-2754 (2018)
Relevance of Alternative Routes of Kynurenic Acid Production in the Brain
Ramos-Chavez LA, et al.
Oxidative Medicine and Cellular Longevity, 2018 (2018)
Kynurenine pathway inhibition as a therapeutic strategy for neuroprotection
Stone TW, et al.
FEBS Journal, 279(8), 1386-1397 (2012)
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