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Merck
CN

A0326

(S)-AMPA

≥97%, AMPA receptor agonist, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C7H10N2O4
CAS Number:
83643-88-3
Molecular Weight:
186.17
UNSPSC Code:
12352200
PubChem Substance ID:
24890421
NACRES:
NA.77
MDL number:
MFCD00672630
Assay:
≥97%
Form:
powder
Quality level:
100

Key Documents

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Product Name

(S)-AMPA, ≥97%

Quality Level

100

assay

≥97%

form

powder

SMILES string

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

InChI key

UUDAMDVQRQNNHZ-YFKPBYRVSA-N

Gene Information

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)

Related Categories

General description

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

Application

(S)-AMPA has been used to selectively eliminate the neural cochlear component of adult barn owls by destroying afferent synapses.
(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.

Biochem/physiol Actions

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

Features and Benefits

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7697
BCCM2118
BCCK1764
BCCJ8852
BCCH5075

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Evoked cochlear potentials in the barn owl
Koppl C and Gleich O
J. Comp. Physiol., 193(6), 601-612 (2007)
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
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
Robert Nisticò et al.
PloS one, 8(1), e54666-e54666 (2013-01-29)
Abnormal use-dependent synaptic plasticity is universally accepted as the main physiological correlate of memory deficits in neurodegenerative disorders. It is unclear whether synaptic plasticity deficits take place during neuroinflammatory diseases, such as multiple sclerosis (MS) and its mouse model, experimental
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)
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Global Trade Item Number

SKUGTIN
A0326-1MG04061825980423
A0326-5MG04061832079080

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