AP5

AP5

Names
IUPAC name 2-amino-5-phosphonopentanoic acid
Identifiers
CAS Number	76326-31-3
ChemSpider	119225
Jmol interactive 3D	Image
PubChem	135342
InChI InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m1/s1 Key: VOROEQBFPPIACJ-SCSAIBSYSA-N InChI=1/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m1/s1 Key: VOROEQBFPPIACJ-SCSAIBSYBE
SMILES O=P(O)(O)CCC[C@@H](N)C(=O)O
Properties
Chemical formula	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)
Solubility in water	Ammonium hydroxide, 50 mg/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 NMDA receptors in micromolar concentrations (~50 µM).

AP5 blocks the cellular analog of classical conditioning in the sea slug Aplysia californica, and has similar effects on Aplysia long-term potentiation (LTP), 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/APV has also been used to study NMDAR-dependent LTP in the mammalian hippocampus.^[2]

In general, AP5 is 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

• AMPA
• AP7 (drug)
• Kainate

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
2. Gustafsson B., Wigström H., Abraham W.C., and Huang Y.Y. Long-Term Potentiation in the Hippocampus Using Depolarizing Current Pulses as the Conditioning Stimulus to Single Volley Synaptic Potentials. Journal of Neuroscience. 1987 March;7(3):774-780

• Cellular Analog of Differential Classical Conditioning in Aplysia: Disruption by the NMDA Receptor Antagonist DL-2-Amino-5-Phosphonovalerate

^ Laube, B; Hirai H, Sturgess M, Betz H, and Kuhse J (1997). "Molecular determinants of antagonists discrimination by NMDA receptor subunits: Analysis of the glutamate binding site on the NR2B subunit". Neuron 18 (3): 493–503. doi:10.1016/S0896-6273(00)81249-0. PMID 9115742.