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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

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