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A8054

Sigma-Aldrich

D(−)-2-Amino-5-phosphonopentanoic acid

NMDA receptor antagonist

Synonym(s):

D(−)-AP-5, D(−)-APV, D-2-Amino-5-phosphonovaleric acid

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About This Item

Empirical Formula (Hill Notation):
C5H12NO5P
CAS Number:
79055-68-8
Molecular Weight:
197.13
MDL number:
MFCD00078839
UNSPSC Code:
12352106
PubChem Substance ID:
24891311
NACRES:
NA.26

Quality Level

100

Assay

≥98% (TLC)

form

powder

optical purity

optical purity: ≥90% (HPLC, Marfey′s reagent)

technique(s)

ligand binding assay: suitable

color

white

mp

245-246 °C

SMILES string

N[C@H](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)/t4-/m1/s1

InChI key

VOROEQBFPPIACJ-SCSAIBSYSA-N

Gene Information

mouse ... Grin2a(14811)
rat ... Grik1(29559) , Grin2a(24409) , Grin2b(24410) , Grin2c(24411) , Grin2d(24412)

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Application

D(-)-2-Amino-5-phosphonopentanoic acid has been used to pretreat BNST (bed nucleus of the stria terminalis) in order to block the induction of anxiety by ORX-A (orexin-A) into the BNST.

Biochem/physiol Actions

NMDA antagonists have muscle relaxation property and are known to offer neuron protection against brain damage induced by ischemia. 2-Amino-5-phosphonopentanoic acid has been proved to block the iontophoresis induced depolarization of NMDA.
Anticonvulsant; potent and selective N-methyl-D-aspartate (NMDA) receptor antagonist; active enantiomer of 2-amino-5-phosphonopentanoic acid.

Storage Class Code

11 - Combustible Solids

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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Paola Conti et al.
European journal of medicinal chemistry, 42(8), 1059-1068 (2007-03-10)
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The Journal of Neuroscience, 9(9), 3040-3057 (1989)
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The induction of long-term potentiation and depression (LTP and LTD) is thought to trigger gene expression and protein synthesis, leading to consolidation of synaptic and neuronal changes. However, while LTP and LTD have been proposed to play important roles for
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Excitatory amino acid transmitters.
J C Watkins et al.
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