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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:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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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
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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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