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5.04535

QNZ46

Synonym(s):

QNZ46, NMDA Antagonist VIII, 4-[6-Methoxy-2-[(1E)-2-(3-nitrophenyl)ethenyl]-4-oxo-3(4H)-quinazolinyl]-Benzoic acid

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About This Item

Empirical Formula (Hill Notation):
C24H17N3O6
CAS Number:
1237744-13-6
Molecular Weight:
443.41
UNSPSC Code:
12352200
MDL number:
MFCD22666391
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
OK to freeze, protect from light
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assay

≥98% (HPLC)

Quality Level

100

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

yellow

solubility

DMSO: 5 mg/mL

storage temp.

2-8°C

InChI

1S/C24H17N3O6/c1-33-19-10-11-21-20(14-19)23(28)26(17-8-6-16(7-9-17)24(29)30)22(25-21)12-5-15-3-2-4-18(13-15)27(31)32/h2-14H,1H3,(H,29,30)/b12-5+

InChI key

GNLVJIICVWDSNI-LFYBBSHMSA-N

General description

A noncompetitive and voltage-independent antagonist selective for NR2C/D containing NMDA receptors (IC50 = 6, 3, 229, and >300 µM for NR2C, NR2D, NR2A, and NR2B, respectively). Inhibition on NR2C/D containing NMDA receptors is glutamate-binding, but not glycine-binding, dependent. Represents a new class of noncompetitive subunit-selective NMDA receptor antagonists. With more than 100-fold selectivity for recombinant NMDA receptors over AMPA and kainate receptors.

Biochem/physiol Actions

Primary Target
NMDA receptors
Target IC50: 6, 3, 229, and >300 →M for NR2C, NR2D, NR2A, and NR2B, respectively.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Slight warming is required for complete solubilization.

Other Notes

Mayer, M., et al. 2013. Annu. Rev. Physiol.75, 1.

Hansen, K., 2011. J. Neurosci.9, 3650.

Mosley, C., et al. 2010. J. Med. Chem.53, 5476.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

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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Kasper B Hansen et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(10), 3650-3661 (2011-03-11)
NMDA receptors are ionotropic glutamate receptors that mediate excitatory synaptic transmission and have been implicated in several neurological diseases. We have evaluated the mechanism of action of a class of novel subunit-selective NMDA receptor antagonists, typified by (E)-4-(6-methoxy-2-(3-nitrostyryl)-4-oxoquinazolin-3(4H)-yl)-benzoic acid (QNZ46).
Cara A Mosley et al.
Journal of medicinal chemistry, 53(15), 5476-5490 (2010-08-06)
We describe a new class of subunit-selective antagonists of N-methyl D-aspartate (NMDA)-selective ionotropic glutamate receptors that contain the (E)-3-phenyl-2-styrylquinazolin-4(3H)-one backbone. The inhibition of recombinant NMDA receptor function induced by these quinazolin-4-one derivatives is noncompetitive and voltage-independent, suggesting that this family
Janesh Kumar et al.
Annual review of physiology, 75, 313-337 (2012-09-15)
X-ray crystal structures for the soluble amino-terminal and ligand-binding domains of glutamate receptor ion channels, combined with a 3.6-Å-resolution structure of the full-length AMPA receptor GluA2 homotetramer, provide unique insights into the mechanisms of the assembly and function of glutamate