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Merck
CN

A5282

DL-2-Amino-5-phosphonopentanoic acid

≥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:
Molecular Weight:
197.13
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
Beilstein/REAXYS Number:
2446389
Form:
solid
Quality level:
Technical Service
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Product Name

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

form

solid

Quality Level

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

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.

Disclaimer

Hygroscopic


pictograms

Exclamation mark

signalword

Warning

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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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)
Maria José Diógenes et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(34), 11750-11762 (2012-08-24)
Parkinson's disease (PD) is the most common representative of a group of disorders known as synucleinopathies, in which misfolding and aggregation of α-synuclein (a-syn) in various brain regions is the major pathological hallmark. Indeed, the motor symptoms in PD are



Global Trade Item Number

SKUGTIN
A5282-50MG04061833375693
A5282-100MG04061833375662
A5282-10MG04061833375679
A5282-25MG04061833375686