GYKI 52466 dihydrochloride

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Cat.No. 1454 - GYKI 52466 dihydrochloride | C17H15N3O2.2HCl | CAS No. 102771-26-6
Description: Selective non-competitive AMPA antagonist
Chemical Name: 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)-benzenamine dihydrochloride
Purity: ≥98% (HPLC)
Datasheet
Citations (10)
Literature

Biological Activity

Selective non-competitive AMPA receptor antagonist (IC50 values are 10-20, ~ 450 and >> 50 μM for AMPA-, kainate- and NMDA-induced responses respectively). Skeletal muscle relaxant and orally-active anticonvulsant. Has anti-proliferative effects in transformed cells. Also available as part of the AMPA Receptor Tocriset™. Also available as part of the Kainate Receptor Tocriset™.

Compound Libraries

GYKI 52466 dihydrochloride is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 366.24
Formula C17H15N3O2.2HCl
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 102771-26-6
PubChem ID 10042240
InChI Key RUBSCPARMVJNKX-UHFFFAOYSA-N
Smiles Cl.Cl.CC1=NN=C(C2=CC=C(N)C=C2)C2=C(C1)C=C1OCOC1=C2

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 16.49 50
water 3.3 10

Preparing Stock Solutions

The following data is based on the product molecular weight 366.24. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.73 mL 13.65 mL 27.3 mL
5 mM 0.55 mL 2.73 mL 5.46 mL
10 mM 0.27 mL 1.37 mL 2.73 mL
50 mM 0.05 mL 0.27 mL 0.55 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Donevan and Rogawsk (1993) GYKI 52466, a 2,3-benzodiazepine, is a highly selective, non-competitive antagonist of AMPA/kainate receptor responses. Neuron 10 51 PMID: 7678966

Paternain et al (1995) Selective antagonism of AMPA receptors unmasks kainate receptor-mediated responses in hippocampal neurons. Neuron 14 185 PMID: 7826635

Rzeski et al (2001) Glutamate antagonists limit tumor growth. Proc.Natl.Acad.Sci.USA 98 6372 PMID: 11331750

Szabados et al (2001) Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655. Brain Res.Bull. 55 387 PMID: 11489346

Tarnawa et al (1989) Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466. Eur.J.Pharmacol. 167 193 PMID: 2574112


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Keywords: GYKI 52466 dihydrochloride, supplier, Selective, non-competitive, AMPA, antagonists, Glutamate, Receptors, iGlur, Ionotropic, GYKI52466, dihydrochloride, AMPA, Receptors, Tocris Bioscience

10 Citations for GYKI 52466 dihydrochloride

Citations are publications that use Tocris products. Selected citations for GYKI 52466 dihydrochloride include:

Kopach et al (2011) Inflammation alters trafficking of extrasynaptic AMPA receptors in tonically firing lamina II neurons of the rat spinal dorsal horn. Pain 152 912 PMID: 21282008

Lobb et al (2010) A dynamic role for GABA receptors on the firing pattern of midbrain dopaminergic neurons. J Neurophysiol 104 403 PMID: 20445035

Santos et al (2009) Transmission efficacy and plasticity in glutamatergic synapses formed by excitatory interneurons of the substantia gelatinosa in the rat spinal cord. PLoS One 4 e8047 PMID: 19956641

Fritsch et al (2009) Pathological alterations in GABAergic interneurons and reduced tonic inhibition in the basolateral amygdala during epileptogenesis. Neuroscience 163 415 PMID: 19540312

Lebrun-Julien et al (2009) Excitotoxic death of retinal neurons in vivo occurs via a non-cell-autonomous mechanism. J Neurosci 29 5536 PMID: 19403821

Du et al (2008) The role of hippocampal GluR1 and GluR2 receptors in manic-like behavior. J Neurosci 28 68 PMID: 18171924

Lin et al (2008) Integrin regulation of cytoplasmic calcium in excitatory neurons depends upon glutamate receptors and release from intracellular stores. J Pharmacol Exp Ther 37 770 PMID: 18289871

Huang et al (2004) Astrocyte glutamate transporters regulate metabotropic glutamate receptor-mediated excitation of hippocampal interneurons. J Neurosci 24 4551 PMID: 15140926

Bao et al (2016) Lentinan produces a robust antidepressant-like effect via enhancing the prefrontal Dectin-1/AMPA receptor signaling pathway Behavioural Brain Research  317 263 PMID: 27693847

Fernandes et al (2014) In vitro ischemia triggers a transcriptional response to down-regulate synaptic proteins in hippocampal neurons. PLoS One 9 e99958 PMID: 24960035


Do you know of a great paper that uses GYKI 52466 dihydrochloride from Tocris? If so please let us know.

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