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A0326

Sigma-Aldrich

(S)-AMPA

≥97%

Synonyme(s) :

(S)-α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid

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About This Item

Formule empirique (notation de Hill):
C7H10N2O4
Numéro CAS:
83643-88-3
Poids moléculaire :
186.17
Numéro MDL:
MFCD00672630
Code UNSPSC :
12352200
ID de substance PubChem :
24890421
Nomenclature NACRES :
NA.77

Pureté

≥97%

Forme

powder

Chaîne SMILES 

Cc1onc(O)c1C[C@H](N)C(O)=O

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)/t5-/m0/s1

Clé InChI

UUDAMDVQRQNNHZ-YFKPBYRVSA-N

Informations sur le gène

human ... GRIA1(2890) , GRIA2(2891) , GRIA4(2893) , GRIK1(2897)
mouse ... Gria1(14799)
rat ... Gria1(50592) , Gria2(29627) , Gria3(29628) , Gria4(29629) , Grik1(29559) , Grik2(54257) , Grik4(24406) , Grin2a(24409) , Grin2b(24410) , Grm6(24419)

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Description générale

AMPA (α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) activates excitatory postsynaptic currents (EPSC).

Application

(S)-AMPA has also been used to activate rostromedial tegmental nucleus (RMTg), to study aversive conditioning in relation with cocaine-induced avoidance behaviors in mice.
(S)-AMPA has been used to selectively eliminate the neural cochlear component of adult barn owls by destroying afferent synapses.

Actions biochimiques/physiologiques

Active enantiomer of (RS)-AMPA zwitterion. Potent agonist at the AMPA subclass of ionotropic glutamate receptors.

Caractéristiques et avantages

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Sigma-Aldrich

A5282

DL-2-Amino-5-phosphonopentanoic acid

Derek Bowie
The Journal of physiology, 590(1), 49-61 (2011-11-23)
AMPA-type ionotropic glutamate receptors (iGluRs) represent the major excitatory neurotransmitter receptor in the developing and adult vertebrate CNS. They are crucial for the normal hardwiring of glutamatergic circuits but also fine tune synaptic strength by cycling into and out of
Interneuron Diversity series: Fast in, fast out-temporal and spatial signal processing in hippocampal interneurons
Jonas P, et al.
Trends in Neurosciences, 27(1), 30-40 (2004)
Evoked cochlear potentials in the barn owl
Koppl C and Gleich O
J. Comp. Physiol., 193(6), 601-612 (2007)
Penelope J Brockie et al.
Neuron, 80(1), 129-142 (2013-10-08)
The strength of synaptic communication at central synapses depends on the number of ionotropic glutamate receptors, particularly the class gated by the agonist AMPA (AMPARs). Cornichon proteins, evolutionarily conserved endoplasmic reticulum cargo adaptors, modify the properties of vertebrate AMPARs when
J Lauridsen et al.
Journal of medicinal chemistry, 28(5), 668-672 (1985-05-01)
The syntheses of (RS)-alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionic acid (9, ATPA), (alpha-RS, beta-RS)-alpha-amino-beta-methyl-3-hydroxy-5-isoxazolepropionic acid (8), (RS)-alpha-amino-3-hydroxy-5-isoxazolebutyric acid (15a), and (RS)-alpha-amino-3-hydroxy-5-isoxazolevaleric acid (15b) are described. The compounds were tested in vitro together with (RS)-alpha-amino-3-hydroxy-5-(bromomethyl)-4-isoxazolepropionic acid (ABPA) as inhibitors of the binding of radioactive-labeled (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
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