Xanthurenic acid

Xanthurenic acid, or xanthurenate, is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B₆) deficient animals after the ingestion of tryptophan.^[1][2]

Xanthurenic acid^[1]

Names
Preferred IUPAC name 4,8-Dihydroxyquinoline-2-carboxylic acid
Other names Xanthuric acid Xanthurenate 8-Hydroxykynurenic acid 4,8-Dihydroxyquinaldic acid
Identifiers
CAS Number	59-00-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:10072 N
ChemSpider	5497 N
ECHA InfoCard	100.000.373
EC Number	200-410-1
KEGG	C02470 N
PubChem CID	5699
UNII	58LAB1BG8J Y
CompTox Dashboard (EPA)	DTXSID90207728
InChI InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15) N Key: FBZONXHGGPHHIY-UHFFFAOYSA-N N InChI=1/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15) Key: FBZONXHGGPHHIY-UHFFFAOYAE
SMILES OC2=CC(C(O)=O)=NC1=C(O)C=CC=C12
Properties
Chemical formula	C10H7NO4
Molar mass	205.169 g·mol−1
Appearance	Yellow crystals
Melting point	286 °C (547 °F; 559 K)
Solubility in water	Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Xanthurenic acid is suspected to be an endogenous agonist for Group II metabotropic glutamate receptors in humans.^[3] It is also known to be a potent VGLUT inhibitor, thereby preventing the movement of glutamate from the cytoplasm into synaptic vesicles, an action that it mediates via competitive blockade of vesicular glutamate transporters (K_i = 0.19 mM).^[4]

In 2015^[update] researchers reported a marked reduction of xanthurenic acid levels in the serum of patients with schizophrenia.^[5] A recent meta-analysis showed that blood xanthurenic acid levels are lower in individuals suffering from bipolar disorder as well.^[6]

Xanthurenic acid has also been shown to induce gametogenesis of Plasmodium falciparum, the parasite that causes malaria.^[7][8] It is found in the gut of the Anopheles mosquito.

See also

• Kynurenic acid
• 7-Chlorokynurenic acid