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AP5
2-Amino-5-phosphonovaleriansäure.svg
IUPAC name
Identifiers
CAS number 76326-31-3 Yes check.svgY
PubChem 135342
SMILES
InChI
InChI key VOROEQBFPPIACJ-SCSAIBSYBE
ChemSpider ID 119225
Properties
Molecular formula C5H12NO5P
Molar mass 197.13 g/mol
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

AP5 or APV ((2R)-amino-5-phosphonovaleric acid; (2R)-amino-5-phosphonopentanoate) is a selective NMDA receptor antagonist that competitively inhibits the ligand (glutamate) binding site of NMDA receptors.[1]

AP5 blocks the cellular analog of classical conditioning in the sea slug Aplysia californica, and has similar effects on Aplysia long-term potentiation, since NMDA receptors are required for both. It is sometimes used in conjunction with the calcium chelator BAPTA to determine whether NMDARs are required for a particular cellular process.

AP5 is generally very fast acting within in vitro preparations, and can block NMDA receptor action at a reasonably small concentration. The active isomer of AP5 is considered to be the D configuration, although many preparations are available as a racemic mixture of D- and L-isomers. It is useful to isolate the action of other glutamate receptors in the brain, i.e. AMPA and kainate receptors.

AP5 can block the conversion of a silent synapse to an active one, since this conversion is NMDA receptor-dependent.

AP5 was developed by Jeff Watkins and Harry Olverman.

See also

References

  1. ^ Morris RG. Synaptic plasticity and learning: selective impairment of learning rats and blockade of long-term potentiation in vivo by the N-methyl-D-aspartate receptor antagonist AP5. Journal of Neuroscience. 1989 Sep;9(9):3040-57. PMID 2552039
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