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A5282

Sigma-Aldrich

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:
76326-31-3
Molecular Weight:
197.13
Beilstein/REAXYS Number:
2446389
MDL number:
MFCD00010515
UNSPSC Code:
12352106
PubChem Substance ID:
24277950
NACRES:
NA.32

product name

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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