Quisqualamine

Quisqualamine
Clinical data
Drug classGABAA receptor agonist; Glycine receptor agonist
ATC code
  • None
Identifiers
  • 2-(2-aminoethyl)-1,2,4-oxadiazolidine-3,5-dione
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC4H7N3O3
Molar mass145.118 g·mol−1
3D model (JSmol)
  • O=C1NC(=O)ON1CCN
  • InChI=1S/C4H7N3O3/c5-1-2-7-3(8)6-4(9)10-7/h1-2,5H2,(H,6,8,9)
  • Key:LIPCXBVXQUFCSC-UHFFFAOYSA-N

Quisqualamine is the α-decarboxylated analogue of the glutamate receptor agonist and neurotoxin quisqualic acid and an analogue of the neurotransmitter γ-aminobutyric acid (GABA).

α-Decarboxylation of excitatory amino acids can produce derivatives with inhibitory effects. Relatedly, unlike quisqualic acid, quisqualamine has central depressant and neuroprotective effects, and appears to act predominantly as an agonist of the GABAA receptor and to a lesser extent as an agonist of the glycine receptor. Its actions are inhibited by GABAA receptor antagonists like bicuculline and picrotoxin and by the glycine receptor antagonist strychnine in vitro.

The NMDA receptor antagonists magnesium and DL-AP5, the AMPA and kainate receptor antagonist CNQX, and the GABAB receptor antagonist 2-hydroxysaclofen all do not affect quisqualamine's actions in vitro. As such, the drug does not appear to interact with the ionotropic glutamate receptors or GABAB receptor.

See also

References

  1. 1 2 3 Evans RH, Francis AA, Hunt K, Martin MR, Watkins JC (June 1978). "Quisqualamine, a novel gamma-aminobutyric acid (GABA) related depressant amino acid". The Journal of Pharmacy and Pharmacology. 30 (6): 364–7. doi:10.1111/j.2042-7158.1978.tb13257.x. PMID 26767. S2CID 84350091.
  2. 1 2 3 4 5 6 Herrero JF (March 1994). "GABAergic activity of quisqualamine and homoquisqualamine in hemisected spinal cord in vitro preparation". Revista Española de Fisiología. 50 (1): 11–7. PMID 7527570.
  3. 1 2 Biraboneye AC, Madonna S, Maher P, Kraus JL (January 2010). "Neuroprotective effects of N-alkyl-1,2,4-oxadiazolidine-3,5-diones and their corresponding synthetic intermediates N-alkylhydroxylamines and N-1-alkyl-3-carbonyl-1-hydroxyureas against in vitro cerebral ischemia". ChemMedChem. 5 (1): 79–85. doi:10.1002/cmdc.200900418. PMID 19943277. S2CID 39067721.