Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and AP5: Difference between pages

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

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477236292

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

| ImageSize = 240px

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

| OtherNames =

|Section1={{Chembox Identifiers

| InChIKey = VOROEQBFPPIACJ-SCSAIBSYBE

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

| CASNo = 76326-31-3

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

| UNII = 39PJ29YY8Z

| PubChem = 135342

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

| 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 =

|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

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

'''AP5''' (also known as '''APV''', '''(2''R'')-amino-5-phosphonovaleric acid''', or '''(2''R'')-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 [[competitive inhibition|competitively inhibits]] the ligand (glutamate) binding site of [[NMDA receptor]]s.<ref>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}}</ref> 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.<ref>[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]</ref> 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.<ref>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

</ref>

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 <small>D</small> configuration, although many preparations are available as a [[racemic]] mixture of <small>D</small>- and <small>L</small>-isomers. It is useful to isolate the action of other [[glutamate]] receptors in the brain, i.e., [[AMPA receptor|AMPA]] and [[kainate receptor]]s.

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

==See also==

*[[AMPA]]

*[[AP7 (drug)]]

*[[Kainate]]

==References==

<references/>

==External links==

* {{cite journal | doi = 10.1016/S0896-6273(00)81249-0 | pmid = 9115742| title = Molecular Determinants of Agonist Discrimination by NMDA Receptor Subunits: Analysis of the Glutamate Binding Site on the NR2B Subunit| date = 1997| last1 = Laube| first1 = Bodo| last2 = Hirai| first2 = Hirokazu| last3 = Sturgess| first3 = Mike| last4 = Betz| first4 = Heinrich| last5 = Kuhse| first5 = Jochen| journal = Neuron| volume = 18| issue = 3| pages = 493–503| doi-access = free}}

{{Ionotropic glutamate receptor modulators}}

[[Category:NMDA receptor antagonists]]

[[Category:Alpha-Amino acids]]

[[Category:Phosphonic acids]]