Quisqualamine

Quisqualamine
Clinical data
Drug class	GABAA receptor agonist; Glycine receptor agonist
ATC code	None;
Identifiers
	IUPAC name 2-(2-aminoethyl)-1,2,4-oxadiazolidine-3,5-dione;
CAS Number	68373-11-5 ;
PubChem CID	3085372;
ChemSpider	2342291;
UNII	PJ4RW6N4EA;
CompTox Dashboard (EPA)	DTXSID60218503 ;
Chemical and physical data
Formula	C4H7N3O3
Molar mass	145.118 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1NC(=O)ON1CCN;
	InChI 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).^[1]^[2]

α-Decarboxylation of excitatory amino acids can produce derivatives with inhibitory effects.^[2] Relatedly, unlike quisqualic acid, quisqualamine has central depressant and neuroprotective effects, and appears to act predominantly as an agonist of the GABA_A receptor and to a lesser extent as an agonist of the glycine receptor.^[1]^[2]^[3] Its actions are inhibited by GABA_A receptor antagonists like bicuculline and picrotoxin and by the glycine receptor antagonist strychnine in vitro.^[1]^[2]^[3]

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

References

^ ^a ^b ^c 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.
^ ^a ^b ^c ^d ^e ^f 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.
^ ^a ^b 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.

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