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5.04528

NVP-AAM077 Tetrasodium Hydrate

Name: NVP-AAM077 Tetrasodium Hydrate
Brand: MM

Synonym(s):

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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About This Item

Empirical Formula (Hill Notation):

C₁₇H₁₇BrN₃Na₄O₆P

CAS Number:

459836-30-7

Molecular Weight:

562.17

UNSPSC Code:

12352200

NACRES:

NA.77

Assay

≥99% (HPLC)

Quality Level

100

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze
protect from light

color

white

solubility

water: 24 mg/mL

storage temp.

−20°C

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

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.

Warning

Toxicity: Standard Handling (A)

Reconstitution

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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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Equilibrium constants for (R)-[(S)-1-(4-bromo-phenyl)-ethylamino]-(2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-methyl]-phosphonic acid (NVP-AAM077) acting at recombinant NR1/NR2A and NR1/NR2B N-methyl-D-aspartate receptors: Implications for studies of synaptic transmission.

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

Restoration of synaptic plasticity and learning in young and aged NCAM-deficient mice by enhancing neurotransmission mediated by GluN2A-containing NMDA receptors.

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.

State-dependent increase of cortical gamma activity during REM sleep after selective blockade of NR2B subunit containing NMDA receptors.

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

Double dissociation of the requirement for GluN2B- and GluN2A-containing NMDA receptors in the destabilization and restabilization of a reconsolidating memory.

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.

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