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Homoquinolinic acid

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Chemical compound Pharmaceutical compound
Homoquinolinic acid
Clinical data
Other namesHomoquinolinate
ATC code
  • None
Identifiers
IUPAC name
  • 3-(Carboxymethyl)-2-pyridinecarboxylic acid
CAS Number
PubChem CID
ChemSpider
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.164.902 Edit this at Wikidata
Chemical and physical data
FormulaC8H7NO4
Molar mass181.147 g·mol
3D model (JSmol)
SMILES
  • c1cc(c(nc1)C(=O)O)CC(=O)O
InChI
  • InChI=1S/C8H7NO4/c10-6(11)4-5-2-1-3-9-7(5)8(12)13/h1-3H,4H2,(H,10,11)(H,12,13)
  • Key:HQPMJFFEXJELOQ-UHFFFAOYSA-N

Homoquinolinic acid (HQA) is a potent excitotoxin that is a conformationally restricted analogue of N-methyl-D-aspartate (NMDA) and a partial agonist of the main/glutamate site of the NMDA receptor, with some selectivity for NR2B subunit-containing receptors. It is approximately equipotent to NMDA and about five times more potent than quinolinic acid as an agonist of the NMDA receptor. HQA has also been found to label a novel yet uncharacterized binding site, which can be distinguished from the NMDA receptor with the use of 2-carboxy-3-carboxymethylquinoline (CCMQ), a selective ligand of the uncharacterized site.

See also

References

  1. Stone TW (1989). Quinolinic acid and the kynurenines. CRC Press. ISBN 978-0-8493-6592-8.
  2. Stolerman IP (31 July 2010). Encyclopedia of Psychopharmacology. Springer Science & Business Media. pp. 511–. ISBN 978-3-540-68698-9.
  3. de Carvalho LP, Bochet P, Rossier J (April 1996). "The endogenous agonist quinolinic acid and the non endogenous homoquinolinic acid discriminate between NMDAR2 receptor subunits". Neurochemistry International. 28 (4): 445–52. doi:10.1016/0197-0186(95)00091-7. PMID 8740453. S2CID 19395334.
  4. Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 404–. ISBN 978-1-60913-345-0.
  5. C.S.A. Neurosciences Abstracts. Cambridge Scientific Abstracts. 1984.
  6. Egebjerg J, Schousboe A, Krogsgaard-Larsen P (4 October 2001). Glutamate and GABA Receptors and Transporters: Structure, Function and Pharmacology. CRC Press. pp. 73–. ISBN 978-0-203-29938-8.
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Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
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