2-(Phosphonomethyl)-pentanedioic Acid

2-(Phosphonomethyl)-pentanedioic acid (2-PMPA) is a potent inhibitor of glutamate carboxypeptidase II (GCP II), also known as N-acetylated alpha-linked dipeptidase (NAALADase), with a Ki value of 98 pM for release of glutamate from the NAALADase peptide substrate N-acetylasparatylglutamate (NAAG). It is selective for GCP II/NAALADase over a panel of 100 receptors, transporters, ion channels, and enzymes at a concentration of 10 µM. 2-PMPA is neuroprotective against hypoxia (EC50 = 8.4 µM), but not veratridine-induced injury, in neuron-enriched primary cultures from rat embryo cerebellum. In vivo, 2-PMPA reduces neuronal cell death induced by middle cerebral artery occlusion via increases in NAAG expression and reduction of glutamate in rats. 2-PMPA (100 mg/kg) blocks the conditioned place preference response to cocaine, but not food, in male rats. It reduces the number of flinches induced by formalin injection into the footpad of mice when administered at a dose of 10 µg per animal, an effect that is reversed by the group II metabotropic glutamate receptor antagonist LY341495. 2-PMPA also decreases severity and delays onset of experimental autoimmune encephalomyelitis (EAE) in mice.Formal Name: 2-(phosphonomethyl)-pentanedioic acid. CAS Number: 173039-10-6. Synonyms: 2-PMPA. Molecular Formula: C6H11O7P. Formula Weight: 226.1. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: PBS (pH 7.2): 10 mg/ml. SMILES: OP(CC(C(O)=O)CCC(O)=O)(O)=O. InChi Code: InChI=1S/C6H11O7P/c7-5(8)2-1-4(6(9)10)3-14(11,12)13/h4H,1-3H2,(H,7,8)(H,9,10)(H2,11,12,13). InChi Key: ISEYJGQFXSTPMQ-UHFFFAOYSA-N.