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A8054

Sigma-Aldrich

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

NMDA receptor antagonist

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C5H12NO5P
Número de CAS:
79055-68-8
Peso molecular:
197.13
MDL number:
MFCD00078839
UNSPSC Code:
12352106
PubChem Substance ID:
24891311
NACRES:
NA.26

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

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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IV-Methyl-D-Aspartate Receptor Antagonist AP5
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European journal of medicinal chemistry, 42(8), 1059-1068 (2007-03-10)
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Orexin-A Induces Anxiety-like Behavior through Interactions with Glutamatergic Receptors in the Bed Nucleus of the Stria Terminalis of Rats
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eLife, 9 (2020-07-01)
Many cortical network models use recurrent coupling strong enough to require inhibition for stabilization. Yet it has been experimentally unclear whether inhibition-stabilized network (ISN) models describe cortical function well across areas and states. Here, we test several ISN predictions, including
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