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MW 197.13 Da, Purity >99%. Competitive NMDA receptor glutamate site antagonist. More active form of DL-AP5.

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Images

Chemical Structure - D-AP5, NMDA glutamate site antagonist (AB120003), expandable thumbnail
  • Cellular Activation - D-AP5, NMDA glutamate site antagonist (AB120003), expandable thumbnail
  • Functional Studies - D-AP5, NMDA glutamate site antagonist (AB120003), expandable thumbnail
  • Functional Studies - D-AP5, NMDA glutamate site antagonist (AB120003), expandable thumbnail

Publications

Key facts

CAS number
79055-68-8
Purity
> 99%
Form
Solid
Molecular weight
197.13 Da
Molecular formula
C5H12NO5P
PubChem identifier
135342
Nature
Synthetic

Alternative names

Recommended products

MW 197.13 Da, Purity >99%. Competitive NMDA receptor glutamate site antagonist. More active form of DL-AP5.

Key facts

Purity
> 99%
PubChem identifier
135342
Biochemical name
5-Phosphono-D-norvaline
Biological description

Competitive NMDA receptor glutamate site antagonist. More active form of DL-AP5.

Canonical SMILES
C(CC(C(=O)O)N)CP(=O)(O)O
Isomeric SMILES
C(C[C@H](C(=O)O)N)CP(=O)(O)O
InChI
InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m1/s1
InChIKey
VOROEQBFPPIACJ-SCSAIBSYSA-N
IUPAC name
(2R)-2-amino-5-phosphonopentanoic acid

Storage

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 info

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

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.

Associated diseases and disorders

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.

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4 product images

  • Chemical Structure - D-AP5, NMDA glutamate site antagonist (ab120003), expandable thumbnail

    Chemical Structure - D-AP5, NMDA glutamate site antagonist (ab120003)

    2D chemical structure image of ab120003, D-AP5, NMDA glutamate site antagonist

  • Cellular Activation - D-AP5, NMDA glutamate site antagonist (ab120003), expandable thumbnail
    Image from Barker M et al., Plos One, 7(5), e35955. Fig 1,; doi: 10.1371/journal.pone.0035955

    Cellular Activation - D-AP5, NMDA glutamate site antagonist (ab120003)

    (A) Photomicrograph of a DCN fusiform cell filled with lucifer yellow (top) and whole cell voltage clamp recording of this fusiform cell while stimulating the LVN (bottom). (B) Photomicrograph of a DCN granule cell filled with lucifer yellow (top) and whole cell voltage clamp recording of this granule cell while stimulating the LVN (bottom). Both cells were held at -68 mV and the LVN was stimulated at 0.3 Hz. Glutamatergic EPSCs are represented in black and are blocked by 50 μm D-AP5 and 10 μm NBQX (traces in red). Each trace represents an average of 10-20 single traces. The arrowhead represents the artifact of stimulus that has been removed for clarity. Scale bar: (A) 50 μm, (B) 20 μm.

  • Functional Studies - D-AP5, NMDA glutamate site antagonist (ab120003), expandable thumbnail
    Image from Herman MA et al., PLoS One. 2011;6(11):e26501. Fig 2(A).; doi: 10.1371/journal.pone.0026501. Reproduced under the Creative Commons license http://creativecommons.org/licenses/by/4.0/

    Functional Studies - D-AP5, NMDA glutamate site antagonist (ab120003)

    Averaged Ca2+ transients (500 Hz line scans) evoked by 40 ms voltage step in a dendrite (left) and spine (right) in control (black), D-AP5 (red, 10 µM), after a 10 min washout of D-AP5 (green), and in 5 µM NMDA (blue). Mibefradil (20 µM), nimodipine (20 µM) and TTX (0.5 µM) were present throughout.

  • Functional Studies - D-AP5, NMDA glutamate site antagonist (ab120003), expandable thumbnail
    Image from Brady JD et al., Neuroscience. 2010;168(1):108-17. Fig 3.; doi: 10.1016/j.neuroscience.2010.03.009 with permission from Elsevier.

    Functional Studies - D-AP5, NMDA glutamate site antagonist (ab120003)

    Representative voltage-clamp recording (Vh= −60 mV, ECl−=+8 mV) of a Purkinje cells response to simulated ischemia and sequential block of glutamate receptors and GABAA receptors.

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