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A5282

Sigma-Aldrich

DL-2-Amino-5-phosphonopentanoic acid

solid

Synonym(s):
5-Phosphono-DL-norvaline, APV, DL-2-Amino-5-phosphonovaleric acid, AP-5
Empirical Formula (Hill Notation):
C5H12NO5P
CAS Number:
Molecular Weight:
197.13
Beilstein:
2446389
MDL number:
PubChem Substance ID:
NACRES:
NA.32

form

solid

color

white

solubility

0.1 M NaOH: 4 mg/mL
H2O: 5.6 mg/mL
organic solvents: insoluble

SMILES string

NC(CCCP(O)(O)=O)C(O)=O

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)

InChI key

VOROEQBFPPIACJ-UHFFFAOYSA-N

Gene Information

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Application

DL-2-Amino-5-phosphonopentanoic acid has been used:
  • in the inactivation of N-methyl-D-aspartate (NMDA)-mediated synapses
  • used in growth medium for inhibition of electrical activity in the neuronal network
  • used to isolate N-methyl-D-aspartate receptors (NMDAR) or α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR)-mediated currents were isolated using this product
  • used in double distilled water to compare its NMDA antagonistic action with that of prion protein (PrPC)

Packaging

10, 25, 50, 100 mg in glass bottle

Biochem/physiol Actions

Anticonvulsant; potent and selective NMDA receptor antagonist.

Caution

Hygroscopic

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Activation of NR2A-containing NMDA receptors is not obligatory for NMDA receptor-dependent long-term potentiation
Weitlauf C, et al.
The Journal of Neuroscience, 25(37), 8386-8390 (2005)
Engineered neuronal circuits shaped and interfaced with carbon nanotube microelectrode arrays
Shein M, et al.
Biomedical Microdevices, 11(2), 495-501 (2009)
Ryota Kobayashi et al.
Frontiers in computational neuroscience, 3, 9-9 (2009-08-12)
Information is transmitted in the brain through various kinds of neurons that respond differently to the same signal. Full characteristics including cognitive functions of the brain should ultimately be comprehended by building simulators capable of precisely mirroring spike responses of
Marijn van Wingerden et al.
Neuron, 76(4), 813-825 (2012-11-28)
Neural activity in orbitofrontal cortex has been linked to flexible representations of stimulus-outcome associations. Such value representations are known to emerge with learning, but the neural mechanisms supporting this phenomenon are not well understood. Here, we provide evidence for a
Bence P Olveczky et al.
PLoS biology, 3(5), e153-e153 (2005-04-14)
Songbirds learn their songs by trial-and-error experimentation, producing highly variable vocal output as juveniles. By comparing their own sounds to the song of a tutor, young songbirds gradually converge to a stable song that can be a remarkably good copy

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