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Details

Stereochemistry ABSOLUTE
Molecular Formula C5H7N3O5
Molecular Weight 189.1262
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUISQUALIC ACID

SMILES

N[C@@H](CN1OC(=O)NC1=O)C(O)=O

InChI

InChIKey=ASNFTDCKZKHJSW-REOHCLBHSA-N
InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1

HIDE SMILES / InChI

Molecular Formula C5H7N3O5
Molecular Weight 189.1262
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Quisqualic acid is an agonist of (AMPA)-subtype glutamate receptor, GRIA2, and group I metabotropic glutamate receptors. Quisqualic acid has been shown to inhibit human glutamate carboxypeptidase II (GCPII), an enzyme occurs in the central nervous system as well as in human prostate (where it is called prostate-specific membrane antigen; PSMA). Inhibitors of this enzyme as was discovered can provide neuroprotection, but can also be useful for the detection, imaging, and treatment of prostate cancer.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q13255|||Q9NU10
Gene ID: 2911.0
Gene Symbol: GRM1
Target Organism: Homo sapiens (Human)
Target ID: P42262
Gene ID: 2891.0
Gene Symbol: GRIA2
Target Organism: Homo sapiens (Human)
Target ID: P41594
Gene ID: 2915.0
Gene Symbol: GRM5
Target Organism: Homo sapiens (Human)
Target ID: Q04609|||Q16305
Gene ID: 2346.0
Gene Symbol: FOLH1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
L-Quisqualic acid transport into hippocampal neurons by a cystine-sensitive carrier is required for the induction of quisqualate sensitization.
2001
Cell type-specific differences in the coupling of recombinant mGlu1alpha receptors to endogenous G protein sub-populations.
2001 Apr
Spinal and supraspinal changes in opioid mRNA expression are related to the onset of pain behaviors following excitotoxic spinal cord injury.
2001 Feb 1
Expression of c-fos mRNA is increased and related to dynorphin mRNA expression following excitotoxic spinal cord injury in the rat.
2001 Jul 20
Reassessment of the Ca2+ sensing property of a type I metabotropic glutamate receptor by simultaneous measurement of inositol 1,4,5-trisphosphate and Ca2+ in single cells.
2001 Jun 1
Excitotoxic model of post-traumatic syringomyelia in the rat.
2001 Sep 1
Glutamate-mediated cytosolic calcium oscillations regulate a pulsatile prostaglandin release from cultured rat astrocytes.
2003 Dec 1
Fluid flow in an animal model of post-traumatic syringomyelia.
2003 Jun
Structure of glutamate analogs that activate the ON bipolar cell metabotropic glutamate receptor in vertebrate retina.
2003 May-Jun
Mutational analysis and molecular modeling of the binding pocket of the metabotropic glutamate 5 receptor negative modulator 2-methyl-6-(phenylethynyl)-pyridine.
2003 Oct
A family of highly selective allosteric modulators of the metabotropic glutamate receptor subtype 5.
2003 Sep
N-methyl-D-aspartate receptor subunit expression and phosphorylation following excitotoxic spinal cord injury in rats.
2003 Sep 25
Excitatory amino acid induced oligodendrocyte cell death in vitro: receptor-dependent and -independent mechanisms.
2004 Sep
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: Incubation of mouse brain sagittal slices with various concentrations of quisqualic acid resulted in significant increase in the leakage of lactate dehydrogenase and potassium from the slices into the medium. Prior incubation of mouse brain slices with NMDA (MK-801 or AP7) or non-NMDA receptor antagonists (GDEE or quinoxalinediones) protected against quisqualic acid-mediated toxicity. Slices prepared from animals pretreated in vivo with MK-801 (5 mg/kg b.wt.) were also resistant to the toxic effects of quisqualic acid, indicating the possible involvement of NMDA receptors in quisqualic acid toxicity.
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:10:58 GMT 2025
Edited
by admin
on Mon Mar 31 19:10:58 GMT 2025
Record UNII
8OC22C1B99
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.BETA.-(3,5-DIOXO-1,2,4-OXODIAZOLIDIN-2-YL)-L-ALANINE
Preferred Name English
QUISQUALIC ACID
MI  
Common Name English
L-QUISQUALIC ACID
Common Name English
QUISQUALIC ACID [MI]
Common Name English
Code System Code Type Description
MESH
D016318
Created by admin on Mon Mar 31 19:10:58 GMT 2025 , Edited by admin on Mon Mar 31 19:10:58 GMT 2025
PRIMARY
PUBCHEM
40539
Created by admin on Mon Mar 31 19:10:58 GMT 2025 , Edited by admin on Mon Mar 31 19:10:58 GMT 2025
PRIMARY
EPA CompTox
DTXSID20896927
Created by admin on Mon Mar 31 19:10:58 GMT 2025 , Edited by admin on Mon Mar 31 19:10:58 GMT 2025
PRIMARY
FDA UNII
8OC22C1B99
Created by admin on Mon Mar 31 19:10:58 GMT 2025 , Edited by admin on Mon Mar 31 19:10:58 GMT 2025
PRIMARY
MERCK INDEX
m9472
Created by admin on Mon Mar 31 19:10:58 GMT 2025 , Edited by admin on Mon Mar 31 19:10:58 GMT 2025
PRIMARY Merck Index
CAS
52809-07-1
Created by admin on Mon Mar 31 19:10:58 GMT 2025 , Edited by admin on Mon Mar 31 19:10:58 GMT 2025
PRIMARY
DRUG BANK
DB02999
Created by admin on Mon Mar 31 19:10:58 GMT 2025 , Edited by admin on Mon Mar 31 19:10:58 GMT 2025
PRIMARY
WIKIPEDIA
QUISQUALIC ACID
Created by admin on Mon Mar 31 19:10:58 GMT 2025 , Edited by admin on Mon Mar 31 19:10:58 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST