PEAQX

PEAQX
Clinical data
Other names	PEAQX
Identifiers
	IUPAC name ({[(1S)-1-(4-bromophenyl)ethyl]amino}-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl)phosphonic acid;
Chemical and physical data
Formula	C17H17BrN3O5P
Molar mass	454.211 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=c2nc1c(nc2=O)cccc1C(P(O)(O)=O)NC(C)c3ccc(Br)cc3;
	(verify)

PEAQX is a competitive antagonist at the NMDA receptor. Although originally described as 100-fold selective for GluN1/GluN2A receptors vs. GluN1/GluN2B receptors, more detailed studies^[1] of the Ki of PEAQX revealed it only shows a 5 fold difference in affinity for GluN1/GluN2A vs. GluN1/GluN2B receptors. It is also a potent anticonvulsant in animal tests.^[2]

References

^ Frizelle PA, Chen PE, Wyllie DJ Equilibrium constants for (R)-[(S)-1-(4-bromo-phenyl)-ethylamino]-(2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-methyl]-phosphonic acid (NVP-AAM077) acting at recombinant NR1/NR2A and NR1/NR2B N-methyl-D-aspartate receptors: Implications for studies of synaptic transmission. Molecular Pharmacology 2006 Sep;70(3):1022-32. PMID 16778008
^ Auberson YP, Allgeier H, Bischoff S, Lingenhoehl K, Moretti R, Schmutz M. 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition. Bioorganic and Medicinal Chemistry Letters. 2002 Apr 8;12(7):1099-102. PMID 11909726

[1] Frizelle PA, Chen PE, Wyllie DJ Equilibrium constants for (R)-[(S)-1-(4-bromo-phenyl)-ethylamino]-(2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-methyl]-phosphonic acid (NVP-AAM077) acting at recombinant NR1/NR2A and NR1/NR2B N-methyl-D-aspartate receptors: Implications for studies of synaptic transmission. Molecular Pharmacology 2006 Sep;70(3):1022-32. PMID 16778008

[2] Auberson YP, Allgeier H, Bischoff S, Lingenhoehl K, Moretti R, Schmutz M. 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition. Bioorganic and Medicinal Chemistry Letters. 2002 Apr 8;12(7):1099-102. PMID 11909726

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