Description
Key facts
CAS number:1202172-03-9,
Purity:>98%,
Form:SolidSee storage information,
Molecular weight:378.4 Da,
Molecular formula:C21H18N2O5,
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
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
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.
