Description
Key facts
CAS number:127910-31-0,
Purity:>99%,
Form:SolidSee storage information,
Molecular weight:209.14 Da,
Molecular formula:C6H12NO5P,
PubChem:5950212,
Nature:Synthetic,
Solubility:Soluble in water to 100 mM (with warming),
Biochemical name:2-Amino-4-methyl-5-phosphono-3-pentenoic acid,
Biological description:Competitive NMDA receptor antagonist (Ki = 35 nM for displacement of CPP binding in rat brain). Potent oral anticonvulsant activity in vivo.,
Canonical smiles:CC(=CC(C(=O)O)N)CP(=O)(O)O,
Isomeric smiles:C/C(=C\C(C(=O)O)N)/CP(=O)(O)O,
InChi:InChI=1S/C6H12NO5P/c1-4(3-13(10,11)12)2-5(7)6(8)9/h2,5H,3,7H2,1H3,(H,8,9)(H2,10,11,12)/b4-2+,
InChiKey:BDYHNCZIGYIOGJ-DUXPYHPUSA-N,
IUPAC Name:(E)-2-amino-4-methyl-5-phosphonopent-3-enoic 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.
NMDAR2A NMDAR2B GluN2C NMDAR1 Glutamate Receptor 1 (AMPA subtype) NMDAR3A + 3B and GluN2D are subunits of ionotropic glutamate receptors specifically the N-methyl-D-aspartate (NMDA) receptor and AMPA receptor subtypes. These receptors are integral membrane proteins involved in synaptic transmission and plasticity. NMDA receptors which include these subunits form a tetrameric structure typically composed of two GluN1 and two GluN2 or GluN3 subunits. The mass of each subunit varies but GluN1 has an approximate molecular weight of 120 kDa. These receptors are primarily expressed in the central nervous system within the neuronal synapses modulating excitatory neurotransmission.
Biological function summary
These receptor subunits play an important role in synaptic plasticity memory and learning by mediating calcium ion influx in response to glutamate binding. They form part of a complex that includes auxiliary proteins that modulate their function and pharmacology. NMDAR subunits assemble to establish functional NMDA receptors requiring co-agonists such as glycine or D-serine and distinguished by their dependence on membrane depolarization to remove the Mg²⁺ block. Meanwhile AMPA receptors through the GluR1 subunit rapidly mediate excitatory postsynaptic potentials.
Pathways
NMDARs and associated subunits participate significantly in the long-term potentiation (LTP) and long-term depression (LTD) pathways essential for synaptic strengthening and weakening. These synaptic plasticity pathways heavily involve signaling proteins such as calcium/calmodulin-dependent protein kinase II (CaMKII) and protein kinase C (PKC). Furthermore the interaction with neuronal nitric oxide synthase (nNOS) links NMDAR activity to downstream signaling cascades which can influence synaptic strength and neuronal health.
Aberrations in NMDA receptor function are implicated in neurological conditions such as Alzheimer's disease and schizophrenia. Reduced NMDAR activity is associated with cognitive decline and synaptic dysfunction in Alzheimer's partly due to interactions with amyloid-beta proteins. In schizophrenia altered expression of NMDAR subunits especially NMDA antagonists like MK-801 and DL-AP5 hint at a dysregulated glutamatergic system contributing to symptoms. Addressing these pathways and interactions provides a foundation for developing therapeutic strategies.
