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

Product Name

D(−)-2-Amino-5-phosphonopentanoic acid, NMDA receptor antagonist

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

SMILES string

N[C@H](CCCP(O)(O)=O)C(O)=O

InChI key

VOROEQBFPPIACJ-SCSAIBSYSA-N

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

Quality Level

100

Gene Information

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

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Related Categories

Amino Acids

Biochemicals

Cell Culture Supplements & Reagents

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

Anticonvulsant; potent and selective N-methyl-D-aspartate (NMDA) receptor antagonist; active enantiomer of 2-amino-5-phosphonopentanoic acid.

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.

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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Certificates of Analysis (COA)

Lot/Batch Number

0000522794

0000522793

0000522792

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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)

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

Activation of the CREB/

Daniela Gandolfi et al.

Frontiers in cellular neuroscience, 11, 184-184 (2017-07-14)

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

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)

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

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