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A8054

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

Name: <SC>D</SC>(−)-2-Amino-5-phosphonopentanoic acid
Brand: SIGMA

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

NACRES:

NA.26

PubChem Substance ID:

24891311

UNSPSC Code:

12352106

MDL number:

MFCD00078839

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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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Related Categories

Biochemicals

Cell Culture Supplements & Reagents

Amino Acids – Building Blocks of Life Science

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis and pharmacological evaluation of novel conformationally constrained homologues of glutamic acid.

Paola Conti et al.

European journal of medicinal chemistry, 42(8), 1059-1068 (2007-03-10)

Twelve novel conformationally constrained homologues of glutamic acid have been synthesized and pharmacologically characterized at ionotropic glutamate receptors (iGluRs). Synthesis of the target compounds involved 1,3-dipolar cycloaddition of nitrile oxides to suitable dipolarophiles. The structure to the compounds has been

Synaptic Plasticity and Learning: Selective Impairment of Learning in
Rats and Blockade of Long-Term Potentiation in viva by the
IV-Methyl-D-Aspartate Receptor Antagonist AP5

R. G. M. Morris

The Journal of Neuroscience, 9(9), 3040-3057 (1989)

Beta-adrenergic receptor activation during distinct patterns of stimulation critically modulates the PKA-dependence of LTP in the mouse hippocampus.

Jennifer N Gelinas et al.

Learning & memory (Cold Spring Harbor, N.Y.), 15(5), 281-289 (2008-04-29)

Activation of beta-adrenergic receptors (beta-ARs) enhances hippocampal memory consolidation and long-term potentiation (LTP), a likely mechanism for memory storage. One signaling pathway linked to beta-AR activation is the cAMP-PKA pathway. PKA is critical for the consolidation of hippocampal long-term memory

Heterosynaptic Plasticity Determines the Set Point for Cortical Excitatory-Inhibitory Balance.

Rachel E Field et al.

Neuron, 106(5), 842-854 (2020-03-28)

Excitation in neural circuits must be carefully controlled by inhibition to regulate information processing and network excitability. During development, cortical inhibitory and excitatory inputs are initially mismatched but become co-tuned or balanced with experience. However, little is known about how

Orexin-A Induces Anxiety-like Behavior through Interactions with Glutamatergic Receptors in the Bed Nucleus of the Stria Terminalis of Rats

Elizabeth A Lungwitz

Physiology & Behavior, 107(5), 726-732 (2012)

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Global Trade Item Number

SKU	GTIN
A8054-1MG	04061826055762
A8054-10MG	04061833391105
A8054-5MG	04061833391112

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