A8054
D(−)-2-Amino-5-phosphonopentanoic acid
NMDA receptor antagonist
Synonyme(s) :
D(−)-AP-5, D(−)-APV, D-2-Amino-5-phosphonovaleric acid
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A propos de cet article
Formule empirique (notation de Hill) :
C5H12NO5P
Numéro CAS:
Poids moléculaire :
197.13
NACRES:
NA.26
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
Service technique
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Laissez-nous vous aiderQuality Level
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)
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.
Classe de stockage
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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Contenu apparenté
Product Information Sheet
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
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
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)