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Merck
CN

G119

GYKI 52466 hydrochloride

≥98% (HPLC), α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonist, solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C17H15N3O2 · HCl
CAS Number:
192065-56-8
Molecular Weight:
329.78
UNSPSC Code:
12352200
PubChem Substance ID:
24277984
NACRES:
NA.77
MDL number:
MFCD00153803
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

Key Documents

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Product Name

GYKI 52466 hydrochloride, solid

SMILES string

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

InChI key

RUBSCPARMVJNKX-UHFFFAOYSA-N

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

assay

≥98% (HPLC)

form

solid

color

yellow

solubility

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

Quality Level

100

Gene Information

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

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Application

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). It has also been used as an AMPA blocker to study the function of glutamate in neuroadapted sindbis virus (NSV) -induced motor neuron death.

Biochem/physiol Actions

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

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.

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000513570
0000513570
0000415614
0000415614
0000153120

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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
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
2013 IEEE International Conference on Solid Dielectrics (ICSD) IEEE 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
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