APV (NMDAR antagonist)

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ImageFile=2-Amino-5-phosphonovaleriansäure.svg
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IUPACName=(R)-2-amino-5-phosphonopentanoic acid
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CASNo=76326-31-3
PubChem=1216
ChemSpiderID = 1179
SMILES=O=C(O)C(N)CCCP(O)(O)=O
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Section2= Chembox Properties
Formula=C₅H₁₂NO₅P
MolarMass=197.126 g/mol
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APV ((2"R")-amino-5-phosphonovaleric acid; AP5, (2"R")-amino-5-phosphonopentanoate) is a selective NMDA receptor (NMDAR) antagonist that competitively inhibits the active site of NMDAR. [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]

APV 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.

APV is generally very fast acting within "in vitro" preparations, and can block NMDA receptor action at a reasonably small concentration. The active isomer of APV 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.

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

APV was developed by Jeff Watkins and Harry Olverman.

ee also

*AP7
*AMPA
*Kainate
*NMDA receptor antagonist

References

* [http://www.jneurosci.org/cgi/content/full/19/23/10595 Cellular Analog of Differential Classical Conditioning in Aplysia: Disruption by the NMDA Receptor Antagonist DL-2-Amino-5-Phosphonovalerate]