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A5282

Sigma-Aldrich

DL-2-Amino-5-phosphonopentanoic acid

≥98% (TLC), solid, NMDA receptor antagonist

Sinónimos:

5-Phosphono-DL-norvaline, DL-2-Amino-5-phosphonovaleric acid, AP-5, APV

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About This Item

Fórmula empírica (notación de Hill):
C5H12NO5P
Número de CAS:
76326-31-3
Peso molecular:
197.13
Beilstein/REAXYS Number:
2446389
MDL number:
MFCD00010515
UNSPSC Code:
12352106
PubChem Substance ID:
24277950
NACRES:
NA.32

Nombre del producto

DL-2-Amino-5-phosphonopentanoic acid, solid

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

rat ... Grik1(29559) , Grin2a(24409) , Grin2b(24410)

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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)

Biochem/physiol Actions

Anticonvulsant; potent and selective NMDA receptor antagonist.

Caution

Hygroscopic

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000077732
0000077732
0000271170
0000271169
0000271168

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Engineered neuronal circuits shaped and interfaced with carbon nanotube microelectrode arrays
Shein M, et al.
Biomedical Microdevices, 11(2), 495-501 (2009)
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)
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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