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G119

Sigma-Aldrich

GYKI 52466 hydrochloride

solid

Synonym(e):

1-(4-Aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine hydrochloride

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10 MG
CHF 166.00
25 MG
CHF 418.00
100 MG
CHF 1’050.00

CHF 166.00

Voraussichtliches Versanddatum12. April 2025

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10 MG
CHF 166.00
25 MG
CHF 418.00
100 MG
CHF 1’050.00

About This Item

Empirische Formel (Hill-System):
C17H15N3O2 · HCl
CAS-Nummer:
192065-56-8
Molekulargewicht:
329.78
MDL-Nummer:
MFCD00153803
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24277984
NACRES:
NA.77

CHF 166.00

Voraussichtliches Versanddatum12. April 2025

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Assay

≥98% (HPLC)

Qualitätsniveau

100

Form

solid

Farbe

yellow

Löslichkeit

DMSO: 0.39 mg/mL
ethanol: 0.4 mg/mL
0.1 M HCl: 0.68 mg/mL
methanol: 1 mg/mL
H2O: >10 mg/mL

SMILES String

Cl[H].CC1=NN=C(c2ccc(N)cc2)c3cc4OCOc4cc3C1

InChI

1S/C17H15N3O2.ClH/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11;/h2-5,7-8H,6,9,18H2,1H3;1H

InChIKey

RUBSCPARMVJNKX-UHFFFAOYSA-N

Angaben zum Gen

human ... GRIA1(2890) , GRIA2(2891) , GRIA3(2892) , GRIA4(2893)

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Anwendung

GYKI 52466 hydrochloride has been used as an α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor selective antagonist in cell viability assays to evaluate the specificity of kainate (KA) effect on cerebellar granule cells (CGCs).[1] It has also been used as an AMPA blocker to study the function of glutamate in neuroadapted sindbis virus (NSV) -induced motor neuron death.[2]

Biochem./physiol. Wirkung

GYKI 52466 serves as an antagonist of several processes, mediated by glutamate.[3]
Selective allosteric AMPA receptor antagonist; anti­convulsant; skeletal muscle relaxant.

Leistungsmerkmale und Vorteile

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.

Rechtliche Hinweise

Sold under exclusive license from the Institute for Drug Research Ltd., Budapest, Hungary.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000415614
0000415614
112M4616V
040M4616
128K46062

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T J Wilding et al.
Molecular pharmacology, 47(3), 582-587 (1995-03-01)
Whole-cell recordings were used to study the antagonism of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)-preferring and kainate-preferring receptors by 2,3-benzodiazepines. Current through kainate-preferring receptors was recorded in rat dorsal root ganglion (DRG) neuron-s, whereas AMPA receptor current was measured in cultured neurons from
29th Colloquium, Protides of Biological Fluids null
53rd National Meeting of the Italian Society of Biochemistry and Molecular Biology (SIB) and National Meeting of Chemistry of Biological Systems ? Italian Chemical Society (SCI - Section CSB) null
S D Donevan et al.
Neuron, 10(1), 51-59 (1993-01-01)
In whole-cell voltage-clamp recordings from cultured rat hippocampal neurons, the 2,3-benzodiazepine GYKI 52466 was a potent antagonist of kainate- and AMPA-activated currents (IC50 values, 7.5 and 11 microM, respectively), but was inactive against N-methyl-D-aspartate (NMDA) or gamma-aminobutyric acid responses. The
S D Donevan et al.
Neuroscience, 87(3), 615-629 (1998-10-03)
Allosteric regulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionate (AMPA) receptors include 2,3-benzodiazepines such as GYKI 52466 and GYKI 53655 and the chaotropic anion thiocyanate that inhibit, and benzothiadiazines such as cyclothiazide that potentiate AMPA receptor currents. Here we sought to determine whether the allosteric
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