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PEAQX

Clinical data
Other names	PEAQX, NVP-AAM077
Identifiers
IUPAC name ({amino}-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl)phosphonic acid
CAS Number	459836-30-7
PubChem CID	9868551
ChemSpider	8044242
UNII	LE8K7M4APN
ChEMBL	ChEMBL273636
Chemical and physical data
Formula	C17H17BrN3O5P
Molar mass	454.217 g·mol
3D model (JSmol)	Interactive image
SMILES C(C1=CC=C(C=C1)Br)NC(C2=C3C(=CC=C2)N=C(C(=N3)O)O)P(=O)(O)O
InChI InChI=1S/C17H17BrN3O5P/c1-9(10-5-7-11(18)8-6-10)19-17(27(24,25)26)12-3-2-4-13-14(12)21-16(23)15(22)20-13/h2-9,17,19H,1H3,(H,20,22)(H,21,23)(H2,24,25,26)/t9-,17?/m0/s1 Key:XXZGNAZRWCBSBK-WFVOFKTRSA-N
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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 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.

References

1. Frizelle PA, Chen PE, Wyllie DJ (September 2006). "Equilibrium constants for (R)--(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. 70 (3): 1022–32. doi:10.1124/mol.106.024042. PMID 16778008. S2CID 14304805.
2. Auberson YP, Allgeier H, Bischoff S, Lingenhoehl K, Moretti R, Schmutz M (April 2002). "5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition". Bioorganic & Medicinal Chemistry Letters. 12 (7): 1099–102. doi:10.1016/s0960-894x(02)00074-4. PMID 11909726.

• NMDA receptor antagonists
• 4-Bromophenyl compounds
• Quinoxalines
• Lactams
• Phosphonic acids