AP5

{{about|the chemical compound|the Star Wars Rebels TV series character|AP-5}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477236292

| ImageFile = 2-Amino-5-phosphonovaleriansäure.svg

| ImageSize = 240px

| PIN = (2R)-2-Amino-5-phosphonopentanoic acid

| OtherNames =

|Section1={{Chembox Identifiers

| InChIKey = VOROEQBFPPIACJ-SCSAIBSYBE

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = VOROEQBFPPIACJ-SCSAIBSYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 76326-31-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 39PJ29YY8Z

| PubChem = 135342

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 119225

| SMILES = O=P(O)(O)CCC[C@@H](N)C(=O)O

| 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

| MeSHName =

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|Section2={{Chembox Properties

| Formula=C₅H₁₂NO₅P

| MolarMass=197.13 g/mol

| Appearance=white solid

| Density=1.529 g/mL

| MeltingPt=

| BoilingPtC= 482.1

| Solubility= Ammonium hydroxide, 50 mg/mL

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|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

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AP5 (also known as APV, (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 selective NMDA receptor antagonist that competitively inhibits the ligand (glutamate) binding site of NMDA receptors.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}} 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.[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] 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.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

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.