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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CASNo').
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{{other uses}}
{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 332497587
| verifiedrevid = 477236183
| ImageFile = AMPA.svg
| ImageFile = AMPA.svg
| ImageSize = 200px
| ImageSize = 200px
| 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 = 1066-51-9
| CASNo = 74341-63-2
| PubChem = 1221
| PubChem = 1221
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 276815
| 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 [[Chemical compound|compound]] that is a specific [[agonist]] for the [[AMPA receptor]], where it mimics the effects of the [[neurotransmitter]] [[Glutamate (neurotransmitter)|glutamate]].<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 [[Chemical compound|compound]] that is a specific [[agonist]] for the [[AMPA receptor]], where it mimics the effects of the [[neurotransmitter]] [[glutamate]].<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 broad categories of [[glutamate receptors]]: [[ionotropic]] receptors and [[metabotropic]] receptors. Ionotropic glutamate receptors are [[ligand gated ion channel]]s whose agonists include AMPA, [[Kainate]] and [[NMDA]]. Metabotropic receptors are [[G-protein coupled receptor]]s and are separated into individual classes. In the [[Chemical synapse|synapse]], 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 [[excitatory postsynaptic potential]]s (EPSP).<ref name=Purves2008/> AMPA receptors are non-specific cationic channels allowing the passage of Sodium and Potassium. The glutamate receptor also is permeable to calcium if it is lacking the GluA2 subunit.
There are several types of glutamatergic ion channels in the central nervous system including AMPA, [[kainic acid]] and [[N-Methyl-D-aspartic acid|''N''-methyl-<small>D</small>-aspartic acid]] (NMDA) channels. In the [[Chemical synapse|synapse]], 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 [[Fast Excitatory Postsynaptic Potential|fast]] [[excitatory postsynaptic potential]]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 [[equilibrium potential]] near 0&nbsp;mV.

AMPA was first synthesized, along with several other [[ibotenic acid]] 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==
* [[Ampakine]]


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


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


[[Category:AMPA receptor modulators]]
[[Category:AMPA receptor agonists]]
[[Category:Amino acids]]
[[Category:Kainate receptor agonists]]
[[Category:Alpha-Amino acids]]
[[Category:Isoxazoles]]
[[Category:Isoxazoles]]
[[Category:Glutamate (neurotransmitter)]]

[[fr:AMPA]]
[[it:Recettore_AMPA]]
[[ja:AMPA]]
[[th:แอมพา]]

Latest revision as of 13:44, 20 January 2024

For other uses, see AMPA (disambiguation).
AMPA
Names
IUPAC name
2-Amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)propanoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
MeSH AMPA
  • InChI=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) checkY
    Key: UUDAMDVQRQNNHZ-UHFFFAOYSA-N checkY
  • 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)
    Key: UUDAMDVQRQNNHZ-UHFFFAOYAT
  • O=C1/C(=C(\ON1)C)CC(N)C(=O)O
Properties
C7H10N2O4
Molar mass 186.167 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid, better known as AMPA, is a compound that is a specific agonist for the AMPA receptor, where it mimics the effects of the neurotransmitter glutamate.[1]

There are several types of glutamatergic ion channels in the central nervous system including AMPA, kainic acid and N-methyl-D-aspartic acid (NMDA) channels. In the synapse, 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.[2] AMPA generates fast excitatory postsynaptic potentials (EPSP).[1] AMPA activates AMPA receptors that are non-selective cationic channels allowing the passage of Na+ and K+ and therefore have an equilibrium potential near 0 mV.

AMPA was first synthesized, along with several other ibotenic acid derivatives, by Krogsgaard-Larsen, Honoré, and others toward differentiating glutamate sensitive receptors from aspartate sensitive receptors.[3]


See also

[edit]

References

[edit]
  1. ^ a b Purves, Dale; George J. Augustine; David Fitzpatrick; William C. Hall; Anthony-Samuel LaMantia; James O. McNamara & Leonard E. White (2008). Neuroscience (4th ed.). Sinauer Associates. pp. 128–33. ISBN 978-0-87893-697-7.
  2. ^ Dinh, L; Nguyen T; Salgado H; Atzori M (2009). "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". Neurochem Res. 34 (11): 1896–906. doi:10.1007/s11064-009-9966-z. PMID 19357950. S2CID 25255160.
  3. ^ Krogsgaard-Larsen, P; Honore T; Hansen JJ; Curtis DR; Lodge D (1980). "New class of glutamate agonist structurally related to ibotenic acid". Nature. 284 (5751): 64–66. Bibcode:1980Natur.284...64K. doi:10.1038/284064a0. PMID 6101908. S2CID 4252428.
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