Description
Key facts
CAS number:126453-07-4,
Form:SolidSee storage information,
Molecular weight:252.2 Da,
Molecular formula:C8H17N2O5P,
PubChem:6603754,
Nature:Synthetic,
Biochemical name:(R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid,
Biological description:Highly potent, competitive NMDA antagonist; more active enantiomer of (RS)-CPP (ab120160). (Ki values are 0.04, 0.3, 0.6 and 2.0 μM at NR1/NR2A, NR1/NR2B, NR1/NR2C and NR1/NR2D, respectively).,
Canonical smiles:C1CN(CC(N1)C(=O)O)CCCP(=O)(O)O,
Isomeric smiles:C1CN(C[C@@H](N1)C(=O)O)CCCP(=O)(O)O,
InChi:InChI=1S/C8H17N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h7,9H,1-6H2,(H,11,12)(H2,13,14,15)/t7-/m1/s1,
InChiKey:CUVGUPIVTLGRGI-SSDOTTSWSA-N,
IUPAC Name:(2R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid
Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions-Ambient, Appropriate long-term storage conditions-Ambient, 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 N-Methyl-D-Aspartate Receptor (NMDAR) subunits such as NMDAR2A NMDAR2B GluN2C NMDAR1 GluN2D NR3A and NR3B are key components of glutamate receptors also including the AMPA subtype Glutamate Receptor 1. These receptors are ionotropic and mediate synaptic transmission in the central nervous system. They are expressed in the brain particularly in regions such as the hippocampus and cortex. NMDAR1 also known as GluN1 serves as an obligatory subunit required for functional receptor assembly. The mass of NMDAR subunits varies; for example the GluN1 subunit has an approximate mass of 120 kDa.
Biological function summary
These glutamate receptor subunits forming part of NMDAR and AMPA receptor complexes modulate synaptic plasticity which underlies learning and memory. NMDARs are tetrameric complexes composed mostly of two GluN1 subunits combined with two region-specific GluN2 (A-D) or GluN3 (A B) subunits creating diversity in function and pharmacological characteristics. The AMPA receptor primarily built of GluA1 through GluA4 subunits contributes to fast excitatory neurotransmission. Together these receptors regulate calcium ion flow into neurons impacting cellular events essential for neural communication and adaptation.
Pathways
NMDARs and AMPA receptors integrate into key neural and signaling pathways such as the long-term potentiation pathway which is essential for memory formation. NMDAR activation allows calcium influx necessary for initiating intracellular signaling cascades. The interactions with proteins like CaMKII and synaptic scaffolds like PSD-95 illustrate the role of these receptors in synaptic and protein signaling networks that adjust synaptic strength.
NMDAR and AMPA receptors have massive implications in neurodegenerative diseases like Alzheimer's and neuropsychiatric disorders such as schizophrenia. Dysregulation in NMDAR function possibly through inadequate blockade by antagonists like D-AP5 or D-APV links to excitotoxicity a condition contributing to neuronal death as seen in Alzheimer's. In schizophrenia altered NMDAR signaling is connected to cognitive dysfunction and both NMDAR and AMPA may serve as therapeutic targets.
