Quinolinic acid

Quinolinic acid

Names
IUPAC name Pyridine-2,3-dicarboxylic acid
Identifiers
CAS Number	89-00-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16675 N
ChEMBL	ChEMBL286204 N
ChemSpider	1037 N
ECHA InfoCard	100.001.704
EC Number	201-874-8
KEGG	C03722 N
MeSH	D017378
PubChem	1066
InChI InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12) N Key: GJAWHXHKYYXBSV-UHFFFAOYSA-N N InChI=1/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12) Key: GJAWHXHKYYXBSV-UHFFFAOYAW
SMILES C1=CC(=C(N=C1)C(=O)O)C(=O)O
Properties
Chemical formula	C7H5NO4
Molar mass	167.12 g/mol
Melting point	185 to 190 °C (365 to 374 °F; 458 to 463 K) (decomposes)
Hazards
Safety data sheet	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Quinolinic acid (abbreviated QUIN or QA), also known as pyridine-2,3-dicarboxylic acid, is a dicarboxylic acid with a pyridine backbone. It is a colorless solid. It is the biosynthetic precursor to nicotine.

Quinolinic acid is a downstream product of the kynurenine pathway, which metabolizes the amino acid tryptophan. It acts as an NMDA receptor agonist.

Quinolinic acid has a potent neurotoxic effect. Studies have demonstrated that quinolinic acid may be involved in many psychiatric disorders, neurodegenerative processes in the brain, as well as other disorders. Within the brain, quinolinic acid is only produced by activated microglia and macrophages.

In 1949 L. Henderson was one of the earliest to describe quinolinic acid. Lapin followed up this research by demonstrating that quinolinic acid could induce convulsions when injected into mice brain ventricles. However, it was not until 1981 that Stone and Perkins showed that quinolinic acid activates the N-methyl-d-aspartate receptor (NMDAR). After this, Schwarcz demonstrated that elevated quinolinic acid levels could lead to axonal neurodegeneration.

One of the earliest reported syntheses of this quinolinic acid was by Zdenko Hans Skraup, who found that methyl-substituted quinolines could be oxidized to quinolinic acid by potassium permanganate.