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A5282

DL-2-Amino-5-phosphonopentanoic acid

Name: <SC>DL</SC>-2-Amino-5-phosphonopentanoic acid
Brand: SIGMA

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₅H₁₂NO₅P

CAS Number:

76326-31-3

Molecular Weight:

197.13

NACRES:

NA.32

PubChem Substance ID:

24277950

UNSPSC Code:

12352106

MDL number:

MFCD00010515

Beilstein/REAXYS Number:

2446389

Form:

solid

Quality level:

200

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Product Name

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

form

solid

Quality Level

200

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)

Related Categories

Bioactive Small Molecules

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.

Other Notes

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

Disclaimer

Hygroscopic

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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)

Made-to-order spiking neuron model equipped with a multi-timescale adaptive threshold.

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

Vocal experimentation in the juvenile songbird requires a basal ganglia circuit.

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

NMDA receptors control cue-outcome selectivity and plasticity of orbitofrontal firing patterns during associative stimulus-reward learning.

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

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Global Trade Item Number

SKU	GTIN
A5282-50MG	04061833375693
A5282-100MG	04061833375662
A5282-25MG	04061833375686
A5282-10MG	04061833375679

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