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Merck
CN

5.04528

NVP-AAM077 Tetrasodium Hydrate

别名:

NVP-AAM077 Tetrasodium Hydrate, NMDA Antagonist VII, NVP-AAM077, [[[(1S)-1-(4-Bromophenyl)ethyl]amino](1,2,3,4-tetrahydro-2,3-dioxo-5-quinoxalinyl)methyl] phosphonic acid tetrasodium hydrate, PEAQX tetrasodium hydrate, NVP-AAM077, [[[(1S)-1-(4-Bromophenyl)ethyl]amino](1,2,3,4-tetrahydro-2,3-dioxo-5-quinoxalinyl)methyl] phosphonic acid tetrasodium hydrate, PEAQX tetrasodium hydrate, NMDA Antagonist VII

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关于此项目

经验公式（希尔记法）:
C17H17BrN3Na4O6P
化学文摘社编号:
459836-30-7
分子量:
562.17
MDL number:
MFCD28716157
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥99% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, protect from light

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SMILES string

[P](=O)(O)(O)C(N[C@@H](C)c3ccc(cc3)Br)c1c2nc(c(nc2ccc1)O)O

InChI

1S/C17H17BrN3O5P/c1-9(10-5-7-11(18)8-6-10)19-17(27(24,25)26)12-3-2-4-13-14(12)21-16(23)15(22)20-13/h2-9,17,19H,1H3,(H,20,22)(H,21,23)(H2,24,25,26)/t9-,17?/m0/s1

InChI key

XXZGNAZRWCBSBK-WFVOFKTRSA-N

assay

≥99% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

white

solubility

water: 24 mg/mL

storage temp.

−20°C

Quality Level

100

General description

A potent antagonist for NMDA receptors. Modestly higher selectivity for the NR2A than for the NR2B containing NMDA receptors (IC50 = 0.015 and 0.078 µM) but insufficient to discriminate between NR2A and NR2B-containing NMDA receptors. Widely used for researches in synaptic plastic, learning and memory, and epilepsy.

Biochem/physiol Actions

Primary Target
NMDA receptors
Target IC50: 0.015 and 0.078 µM for 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.

Other Notes

Frizelle. P., et al. 2006. Mol. Pharmacol.70, 1022.
Milton, A., et al. 2013. J. Neurosci.33, 1109.
Kochlamazashvili, G., et al. 2012. J. Neurosci.32, 2263.
Kocsis, B., et al. 2012. Sleep.35, 1011.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

存储类别

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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Pamela A Frizelle et al.
Molecular pharmacology, 70(3), 1022-1032 (2006-06-17)
We have quantified the effects of the N-methyl-d-aspartate (NMDA) receptor antagonist (R)-[(S)-1-(4-bromo-phenyl)-ethylamino]-(2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-methyl]-phosphonic acid (NVP-AAM077) at rat recombinant N-methyl-D-aspartate receptor (NR)1/NR2A and NR1/NR2B NMDA receptors expressed in Xenopus laevis oocytes. We observed no difference in the steady-state levels of inhibition produced
Gaga Kochlamazashvili et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(7), 2263-2275 (2012-03-08)
Neural cell adhesion molecule (NCAM) is the predominant carrier of the unusual glycan polysialic acid (PSA). Deficits in PSA and/or NCAM expression cause impairments in hippocampal long-term potentiation and depression (LTP and LTD) and are associated with schizophrenia and aging.
Bernat Kocsis
Sleep, 35(7), 1011-1016 (2012-07-04)
Sub-anesthetic doses of NMDA receptor antagonists suppress sleep and elicit continuous high-power gamma oscillations lasting for hours. This effect is subunit-specific, as it was also seen after preferential blockade of the NR2A but not of the NR2B subunit-containing receptors. The
Amy L Milton et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(3), 1109-1115 (2013-01-18)
Signaling at NMDA receptors (NMDARs) is known to be important for memory reconsolidation, but while most studies show that NMDAR antagonists prevent memory restabilization and produce amnesia, others have shown that GluN2B-selective NMDAR antagonists prevent memory destabilization, protecting the memory.

相关内容

Pathways and Biomarkers of Glutamatergic Synapse Flyer

Glutamate is an excitatory neurotransmitter found in the synaptic vesicles of glutamatergic synapses. The post-synaptic neurons in these synapses contain ionotropic and metabotropic glutamate receptors. Glutamate binds to AMPA (α-amino-3-hydroxy-5- methylisoxazole-4-propionic acid) subtype glutamate receptors, leading to sodium influx into the post-synaptic cell and resulting in neuronal excitability and synaptic transmission. The NMDA (N-methyl-d-aspartate) subtype glutamate receptors, on the other hand, regulate synaptic plasticity, and can influence learning and memory. The metabotropic g-protein coupled mGluRs modulate downstream calcium signaling pathways and indirectly influence the synapse’s excitability. The synaptic architecture includes intracellular scaffolding proteins (PSD-95, GRIP), intercellular cell adhesion molecules (NCAMs, N-Cadherins), and a variety of signaling proteins (CaMKII/PKA, PP1/PP2B). Processes critical for synaptic transmission and plasticity are influenced by these molecules and their interactions. When the function of these molecules is disrupted, it leads to synaptic dysfunction and degeneration, and can contribute to dementia as seen in Alzheimer’s disease.

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