 | |
| Names | |
|---|---|
| Preferred IUPAC name (2R)-2-Amino-5-phosphonopentanoic acid | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider |
|
| ECHA InfoCard | 100.150.904 |
| UNII | |
| |
| |
| Properties | |
| C5H12NO5P | |
| Molar mass | 197.13 g/mol |
| Appearance | white solid |
| Density | 1.529 g/mL |
| Boiling point | 482.1 °C (899.8 °F; 755.2 K) |
| Ammonium hydroxide, 50 mg/mL | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
AP5 (also known asAPV,(2R)-amino-5-phosphonovaleric acid, or(2R)-amino-5-phosphonopentanoate) is a chemical compound used as a biochemical tool to study various cellular processes. It is a selectiveNMDA receptor antagonist thatcompetitively inhibits the ligand (glutamate) binding site ofNMDA receptors.[1] AP5 blocks NMDA receptors in micromolar concentrations (~50 μM).
AP5 blocks the cellular analog ofclassical conditioning in the sea slugAplysia californica, and has similar effects onAplysialong-term potentiation (LTP), since NMDA receptors are required for both.[2] It is sometimes used in conjunction with thecalciumchelatorBAPTA to determine whether NMDARs are required for a particular cellular process. AP5/APV has also been used to study NMDAR-dependent LTP in the mammalian hippocampus.[3]
In general, AP5 is very fast-acting withinin vitro preparations, and can block NMDA receptor action at a reasonably small concentration. The activeisomer of AP5 is considered to be theD configuration, although many preparations are available as aracemic mixture ofD- andL-isomers. It is useful to isolate the action of otherglutamate receptors in the brain, i.e.,AMPA andkainate receptors.
AP5 can block the conversion of asilent synapse to an active one, since this conversion is NMDA receptor-dependent.
