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AB120047

cis-PPDA, GluN2C/GluN2D NMDA antagonist

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(5 Publications)

MW 378.4 Da, Purity >98%. Potent GluN2C/GluN2D (formerly NR2C / NR2D)-preferring NMDA receptor antagonist. (Ki values for recombinant rat receptors are 0.096 (NR2C), 0.125 (NR2D), 0.55 (NR2A) and 0.31 μM (NR2B)).

View Alternative Names

AMPA 1, AMPA-selective glutamate receptor 1, AW490526, EB11, EIEE27, EPND, FESD, GLUH1, GRIA1_HUMAN, GRIN 2A, GRIN 2B, GluA1, GluN1, GluN2A, GluN2C, GluN2D, GluR-1, GluR-A, GluR-K1, Glutamate Receptor Ionotropic N Methyl D Aspartate 2B, Glutamate Receptor Ionotropic N Methyl D Aspartate 2C, Glutamate Receptor Ionotropic N Methyl D Aspartate subunit 2B, Glutamate [NMDA] receptor subunit epsilon-1, Glutamate [NMDA] receptor subunit epsilon-2, Glutamate [NMDA] receptor subunit epsilon-3, Glutamate [NMDA] receptor subunit epsilon-4, Glutamate [NMDA] receptor subunit zeta-1, Glutamate receptor, Glutamate receptor 1, Glutamate receptor ionotropic, Glutamate receptor ionotropic AMPA 1, Glutamate receptor ionotropic N methyl D aspartate 1, Glutamate receptor ionotropic N methyl D aspartate 2A, Glutamate receptor ionotropic NMDA2B, Glutamate receptor ionotropic, N-methyl-D aspartate, subunit 1, Glutamate receptor ionotropic, NMDA 2C, Glutamate receptor subunit epsilon 2, Glutamate receptor, ionotropic, N-methyl D-aspartate 2D, Glutamate receptor, ionotropic, NMDA2B (epsilon 2), Grin2c, Grin2d, HBGR1, LKS, MGC133252, MGC142178, MGC142180, MRD6, MRD8, N Methly D Aspartate Receptor Channel Subunit Epsilon 3, N methyl D asparate receptor channel subunit epsilon 2, N methyl D aspartate receptor channel subunit zeta 1, N methyl D aspartate receptor channel, subunit epsilon 1, N methyl D aspartate receptor subunit 2A, N methyl D aspartate receptor subunit 2B, N methyl D aspartate receptor subunit 2C, N methyl d aspartate receptor subunit 2D, N-methyl D-aspartate receptor subtype 2A, N-methyl D-aspartate receptor subtype 2B, N-methyl D-aspartate receptor subtype 2C, N-methyl D-aspartate receptor subtype 2D, N-methyl-D-aspartate receptor, N-methyl-D-aspartate receptor subunit 3, N-methyl-D-aspartate receptor subunit NR1, NMD-R1, NMDA 1, NMDA 2D, NMDA NR2B, NMDA receptor 1, NMDA receptor subtype 2A, NMDAR, NMDAR2C, NMDAR2D, NMDE1_HUMAN, NMDE2_HUMAN, NMDE3_HUMAN, NMDE4_HUMAN, NMDZ1_HUMAN, NR1, NR2A, NR2B, NR2C, NR2D, NR3, OTTHUMP00000041930, OTTHUMP00000160135, OTTHUMP00000160643, OTTHUMP00000165781, OTTHUMP00000174531, OTTHUMP00000224241, OTTHUMP00000224242, OTTHUMP00000224243, estrogen receptor binding CpG island, glutamate receptor ionotropic NMDA 2D, glutamate receptor ionotropic, NMDA 1, hNR 3, hNR2A

1 Images
Chemical Structure - cis-PPDA, GluN2C/GluN2D NMDA antagonist (AB120047)
  • Chemical Structure

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Chemical Structure - cis-PPDA, GluN2C/GluN2D NMDA antagonist (AB120047)

2D chemical structure image of ab120047, cis-PPDA, GluN2C/GluN2D NMDA antagonist

Key facts

CAS number

1202172-03-9

Purity

>98%

Form

Solid

form

Molecular weight

378.4 Da

Molecular formula

C<sub>2</sub><sub>1</sub>H<sub>1</sub><sub>8</sub>N<sub>2</sub>O<sub>5</sub>

PubChem

10293029

Nature

Synthetic

Solubility

Soluble in 2 eq. NaOH to 50 mM (with warming)

Biochemical name

1-(Phenanthrene-2-carbonyl)piperazine-2,3-dicarboxylic acid

Biological description

Potent GluN2C/GluN2D (formerly NR2C / NR2D)-preferring NMDA receptor antagonist. (Ki values for recombinant rat receptors are 0.096 (NR2C), 0.125 (NR2D), 0.55 (NR2A) and 0.31 μM (NR2B)).

Canonical smiles

C1CN(C(C(N1)C(=O)O)C(=O)O)C(=O)C2=CC3=C(C=C2)C4=CC=CC=C4C=C3

InChi

InChI=1S/C21H18N2O5/c24-19(23-10-9-22-17(20(25)26)18(23)21(27)28)14-7-8-16-13(11-14)6-5-12-3-1-2-4-15(12)16/h1-8,11,17-18,22H,9-10H2,(H,25,26)(H,27,28)

InChiKey

IWWXIZOMXGOTPP-UHFFFAOYSA-N

IUPAC Name

1-(phenanthrene-2-carbonyl)piperazine-2,3-dicarboxylic acid

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Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

The targets NMDAR2A NMDAR2B GluN2C and GluN2D are subunits of the NMDA receptor also commonly referred to as NMDAR. Additionally NMDAR1 and the Glutamate Receptor 1 (AMPA subtype) are related receptors in the glutamate receptor family. These receptors mediate synaptic transmission and plasticity in the central nervous system primarily in the brain. Particularly the NMDA receptors have a complex structure composed of different subunits each contributing to their biophysical properties. The mass of a full NMDA receptor complex can vary greatly but individual subunits like NMDAR1 typically weigh around 120 kDa. These receptors are expressed mainly in neurons throughout the brain.
Biological function summary

NMDA and AMPA receptors are important for excitatory neurotransmission and synaptic plasticity associated with learning and memory processes. They form part of a larger protein complex known as the postsynaptic density which includes other proteins such as scaffolding proteins and kinases that modulate their activity. NMDAR activation requires the binding of glutamate and glycine while the AMPA receptors get activated solely by glutamate. Each receptor subtype fine-tunes the synaptic responses and integration in neuronal circuits playing a complementary and interconnected role in brain signaling.

Pathways

NMDA and AMPA receptors are central components of the synaptic plasticity pathway particularly long-term potentiation (LTP) and long-term depression (LTD). These pathways are pivotal for synaptic strength adjustments. NMDAR activation initiates intracellular signaling cascades involving proteins like CaMKII and CREB which are vital for synaptic remodeling and memory formation. AMPA receptors are also essential players in these pathways being trafficked to or removed from the synaptic membrane in response to NMDAR activation modulating synaptic strength.

NMDA receptor dysregulation has strong links to neurodegenerative diseases such as Alzheimer's disease and neuropsychiatric disorders like schizophrenia. The dysfunction of these receptors may lead to excessive calcium influx contributing to excitotoxicity and neuronal damage. In Alzheimer's disease amyloid-beta peptides are known to affect NMDA receptor function. Schizophrenia involves alterations in synaptic signaling pathways in which both NMDAR and AMPA receptor subtypes are implicated potentially affecting cognitive and behavioral processes.
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Product protocols

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Publications (5)

Recent publications for all applications. Explore the full list and refine your search

Nature communications 9:1032 PubMed29531223

2018

Vesicular glutamate release from central axons contributes to myelin damage.

Applications

Unspecified application

Species

Unspecified reactive species

Sean Doyle,Daniel Bloch Hansen,Jasmine Vella,Peter Bond,Glenn Harper,Christian Zammit,Mario Valentino,Robert Fern

BMC neuroscience 12:103 PubMed21991932

2011

Neuregulin1/ErbB4-induced migration in ST14A striatal progenitors: calcium-dependent mechanisms and modulation by NMDA receptor activation.

Applications

Unspecified application

Species

Unspecified reactive species

Giulia Pregno,Pollyanna Zamburlin,Giovanna Gambarotta,Silvia Farcito,Valentina Licheri,Federica Fregnan,Isabelle Perroteau,Davide Lovisolo,Patrizia Bovolin

Journal of neuroscience research 89:73-85 PubMed21046566

2010

Whisker experience modulates long-term depression in neocortical γ-aminobutyric acidergic interneurons in barrel cortex.

Applications

Unspecified application

Species

Unspecified reactive species

Qian-Quan Sun,Zhi Zhang

Developmental neurobiology 71:221-45 PubMed20936660

2010

Development of NMDA NR2 subunits and their roles in critical period maturation of neocortical GABAergic interneurons.

Applications

Unspecified application

Species

Unspecified reactive species

Zhi Zhang,Qian-Quan Sun

The Journal of neuroscience : the official journal of the Society for Neuroscience 28:11685-94 PubMed18987204

2008

Extrasynaptic NR2D-containing NMDARs are recruited to the synapse during LTP of NMDAR-EPSCs.

Applications

Unspecified application

Species

Unspecified reactive species

Sarah C Harney,David E Jane,Roger Anwyl
View all publications
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