Quisqualamine

Quisqualamine is the α-decarboxylated analogue of quisqualic acid, as well as a relative of the neurotransmitters glutamate and γ-aminobutyric acid (GABA).^[1][2] α-Decarboxylation of excitatory amino acids can produce derivatives with inhibitory effects.^[2] Indeed, unlike quisqualic acid, quisqualamine has central depressant and neuroprotective properties and appears to act predominantly as an agonist of the GABA_A receptor and also to a lesser extent as an agonist of the glycine receptor, due to the facts that its actions are inhibited in vitro by GABA_A antagonists like bicuculline and picrotoxin and by the glycine antagonist strychnine, respectively.^[1][2][3] Mg²⁺ and DL-AP5, NMDA receptor blockers, CNQX, an antagonist of both the AMPA and kainate receptors, and 2-hydroxysaclofen, a GABA_B receptor antagonist, do not affect quisqualamine's actions in vitro, suggesting that it does not directly affect the ionotropic glutamate receptors or the GABA_B receptor in any way.^[2] Whether it binds to and acts upon any of the metabotropic glutamate receptors like its analogue quisqualic acid however is unclear.

Quisqualamine

Names
IUPAC name 2-(2-aminoethyl)-1,2,4-oxadiazolidine-3,5-dione
Identifiers
CAS Number	68373-11-5 Y
3D model (JSmol)	Interactive image
ChemSpider	2342291
PubChem CID	3085372
UNII	PJ4RW6N4EA Y
CompTox Dashboard (EPA)	DTXSID60218503
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 InChI=1/C4H7N3O3/c5-1-2-7-3(8)6-4(9)10-7/h1-2,5H2,(H,6,8,9) Key: LIPCXBVXQUFCSC-UHFFFAOYAA
SMILES O=C1NC(=O)ON1CCN
Properties
Chemical formula	C4H7N3O3
Molar mass	145.118 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

See also

• Quisqualic acid
• Muscimol

References

1. 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. 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. 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.