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Revision as of 12:44, 20 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').← Previous edit Latest revision as of 23:44, 16 December 2024 edit undoArthurfragoso (talk | contribs)Extended confirmed users2,009 edits Fixes image on dark mode 
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{{other uses}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 332497587 | verifiedrevid = 477236183
| ImageFile = AMPA.svg | ImageFile = AMPA.svg
| ImageSize = 200px | ImageSize = 200px
| ImageClass = skin-invert
| IUPACName = 2-amino-3-(5-methyl-3-oxo-1,2-<br>oxazol-4-yl)propanoic acid | IUPACName = 2-Amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)propanoic acid
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| InChIKey = UUDAMDVQRQNNHZ-UHFFFAOYAT | IUPHAR_ligand = 4131
| InChIKey = UUDAMDVQRQNNHZ-UHFFFAOYAT
| CASNo_Ref = {{cascite}} | CASNo_Ref = {{cascite|changed|??}}
| CASNo = <!-- blanked - oldvalue: 1066-51-9 --> | CASNo = 74341-63-2
| PubChem = 1221 | PubChem = 1221
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 13378 | ChEMBL = 276815
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02057 | DrugBank = DB02057
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = C13672
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| KEGG = C11033
⚫ | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12) | StdInChI = 1S/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UUDAMDVQRQNNHZ-UHFFFAOYSA-N | StdInChIKey = UUDAMDVQRQNNHZ-UHFFFAOYSA-N
| SMILES = O=C1/C(=C(\ON1)C)CC(N)C(=O)O | SMILES = O=C1/C(=C(\ON1)C)CC(N)C(=O)O
| InChI = 1/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12) | InChI = 1/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1184 | ChemSpiderID = 1184
| MeSHName = AMPA | MeSHName = AMPA
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=7|H=10|N=2|O=4 | C=7 | H=10 | N=2 | O=4
| Appearance =
| MolarMass = 186.17 g/mol
| Appearance = | Density =
| Density = | MeltingPt =
| MeltingPt = | BoilingPt =
| BoilingPt = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| Solubility = | MainHazards =
| MainHazards = | FlashPt =
| FlashPt = | AutoignitionPt =
| Autoignition =
}} }}
}} }}


⚫ '''α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid''', better known as '''AMPA''', is a ] that is a specific ] for the ], where it mimics the effects of the ] ].<ref name=Purves2008>{{cite book |author=Purves, Dale |author2=George J. Augustine |author3=David Fitzpatrick |author4=William C. Hall |author5=Anthony-Samuel LaMantia |author6=James O. McNamara |author7=Leonard E. White |name-list-style=amp|title=Neuroscience|edition=4th|publisher=Sinauer Associates|pages=128–33|year=2008|isbn=978-0-87893-697-7}}</ref>
'''AMPA''' (2-amino-3-(5-methyl-3-oxo-1,2-
⚫ oxazol-4-yl)propanoic acid) is a ] that is a specific ] for the ], where it mimics the effects of the ] ].<ref name=Purves2008>{{cite book|author=Purves, Dale, George J. Augustine, David Fitzpatrick, William C. Hall, Anthony-Samuel LaMantia, James O. McNamara, and Leonard E. White|title=Neuroscience. 4th ed.|publisher=Sinauer Associates|pages=128–33|year=2008|isbn=978-0-87893-697-7}}</ref>


There are two types of ]s whose agonists include AMPA, ] and ]. In the ], these two classes of receptors serve very different purposes. AMPA can be used experimentally to distinguish the activity of one receptor from the other in order to understand their differing functions.<ref name=Dinh2009>{{cite journal|last1=Dinh|first1=L|coauthors=Nguyen T, Salgado H, Atzori M|title=Norepinephrine homogeneously inhibits alpha-amino-3-hydroxyl-5-methyl-4-isoxazole-propionate- (AMPAR-) mediated currents in all layers of the temporal cortex of the rat|journal=Neurochem Res|volume=34|issue=11|pages=1896–906|year=2009|pmid=19357950|doi=10.1007/s11064-009-9966-z}}</ref> AMPA generates fast ]s (EPSP).<ref name=Purves2008/> AMPA activates ]s that are non-selective cationic channels allowing the passage of Na+ and K+ and therefore have an ] near 0 mV. There are several types of glutamatergic ion channels in the central nervous system including AMPA, ] and ] (NMDA) channels. In the ], these receptors serve very different purposes. AMPA can be used experimentally to distinguish the activity of one receptor from the other in order to understand their differing functions.<ref name=Dinh2009>{{cite journal|last1=Dinh|first1=L|author2=Nguyen T |author3=Salgado H |author4=Atzori M |title=Norepinephrine homogeneously inhibits alpha-amino-3-hydroxyl-5-methyl-4-isoxazole-propionate- (AMPAR-) mediated currents in all layers of the temporal cortex of the rat|journal=Neurochem Res|volume=34|issue=11|pages=1896–906|year=2009|pmid=19357950|doi=10.1007/s11064-009-9966-z|s2cid=25255160}}</ref> AMPA generates ] ]s (EPSP).<ref name=Purves2008/> AMPA activates AMPA receptors that are non-selective cationic channels allowing the passage of Na<sup>+</sup> and K<sup>+</sup> and therefore have an ] near 0&nbsp;mV.

AMPA was first synthesized, along with several other ] derivatives, by Krogsgaard-Larsen, Honoré, and others toward differentiating glutamate sensitive receptors from aspartate sensitive receptors.<ref name = KrogsgaardLarsen1980>{{cite journal |last1=Krogsgaard-Larsen|first1=P|author2=Honore T |author3=Hansen JJ |author4=Curtis DR|author5=Lodge D |title=New class of glutamate agonist structurally related to ibotenic acid|journal=Nature|volume=284|pages=64–66|year=1980|issue=5751|pmid=6101908|doi=10.1038/284064a0|bibcode=1980Natur.284...64K|s2cid=4252428}}</ref>



==See also==
* ]


==References== ==References==
{{reflist}} {{Reflist|2}}


{{Ionotropic glutamate receptor modulators}}
{{Glutamate_receptor_ligands}}


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