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Key Documents

G7798

Sigma-Aldrich

GYKI-53655 hydrate

>99.0% (HPLC)

Synonym(s):

1-(4-aminophenyl)-3-methylcarbamyl-4-methyl-3,4-dihydro-7,8-methylenedioxy-5H-2,3-benzodiazepine hydrochloride, 5-(4-Aminophenyl)-8,9-dihydro-N,8-dimethyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carboxamide hydrochloride, LY300168 hydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C19H20N4O3 · HCl · xH2O
CAS Number:
143692-48-2
Molecular Weight:
388.85 (anhydrous basis)
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

>99.0% (HPLC)

form

powder

color

yellow to orange

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

InChI

1S/C19H20N4O3.ClH/c1-11-7-13-8-16-17(26-10-25-16)9-15(13)18(22-23(11)19(24)21-2)12-3-5-14(20)6-4-12;/h3-6,8-9,11H,7,10,20H2,1-2H3,(H,21,24);1H

InChI key

ASLCSBBDVWPSQT-UHFFFAOYSA-N

Application

GYKI-53655 hydrate has been used as a calcium-permeable α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPA) receptor antagonist in single-particle tracking experiments.

Biochem/physiol Actions

GYKI-53655 also inhibits the kainate GluK3 homomeric and GluK2/3 heteromeric receptors. It exhibits anti-ischemic, anti-convulsant, and acute neuroprotective activity.
GYKI-53655 is an AMPA antagonist and noncompetitive negative allosteric modulator.

Features and Benefits

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T Szabados et al.
Brain research bulletin, 55(3), 387-391 (2001-08-08)
GYKI 52466 [1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine], a non-competitive AMPA [alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate] and kainate receptor antagonist and its two analogues, GYKI 53405 [1-(4-aminophenyl)-3-acetyl-4-methyl-3,4-dihydro-7,8-methylenedioxy-5H-2,3-benzodiazepine] and GYKI 53655 [1-(4-aminophenyl)-3-methylcarbamyl-4-methyl-3,4-dihydro-7,8-methylenedioxy-5H-2,3-benzodiazepine] were investigated in two seizure models and in MgCl2 induced global cerebral ischaemia, as an acute neuroprotective model.
David Perrais et al.
Neuropharmacology, 56(1), 131-140 (2008-09-02)
A number of kainate receptor antagonists have shown selectivity for receptors containing the GluK1 subunit. Here, we analyze the effects of these GluK1 antagonists on currents mediated by recombinant homomeric GluK3 and heteromeric GluK2/3 receptors expressed in HEK 293 cells
Alice Polenghi et al.
Cell reports, 31(10), 107735-107735 (2020-06-11)
Kainate receptors (KARs) mediate postsynaptic currents with a key impact on neuronal excitability. However, the molecular determinants controlling KAR postsynaptic localization and stabilization are poorly understood. Here, we exploit optogenetic and single-particle tracking approaches to study the role of KAR

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