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5652-28-8

5652-28-8 Structure

5652-28-8 Structure
IdentificationBack Directory
[Name]

(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST
[CAS]

5652-28-8
[Synonyms]

2-AP3
Alanine, 3-phosphono-
2-Amino-3-phosphonopropionic acid
(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST
[Molecular Formula]

C3H8NO5P
[MDL Number]

MFCD00014350
[MOL File]

5652-28-8.mol
[Molecular Weight]

169.07
Chemical PropertiesBack Directory
[Boiling point ]

481.6±55.0 °C(Predicted)
[density ]

1.763±0.06 g/cm3(Predicted)
[solubility ]

PBS (pH 7.2): 2 mg/ml
[form ]

White powder.
[pka]

1.22±0.10(Predicted)
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501
[HS Code ]

2931499090
Hazard InformationBack Directory
[Description]

Metabotropic glutamate receptors (mGluR1-8) are G protein-coupled receptors that function to modulate brain excitatory signaling via presynaptic, postsynaptic, and glial mechanisms. DL-AP3 is a competitive mGluR1 antagonist that demonstrates a Ki value of 298 μM and an IC50 value of 1mM for rat mGluR1α when challenged with glutamate. DL-AP3 can antagonize excitatory amino acid-induced phosphoinositide hydrolysis, induce Ca2+ mobilization in rat hippocampal slices, and inhibit phosphoserine phosphatase in rat brain cortex. At concentrations from 10-300 μM DL-AP3 has been used to characterize the role of mGluR in long-term potentiation in the hippocampus in a model of learning and memory, the release of glutamate in Parkinson’s disease, and the increased activity of mGluR implicated in fragile X syndrome.
[Uses]

DL-2-Amino-3-phosphonopropionic acid (AP3) is an inhibitor of phosphoserine phosphatase and mGluR. Also known as the antagonist of a receptor that is coupled to phosphoinositide metabolism in brain slices. D,L-2-Amino-3-phosphonopropionic acid is also an inhibitor of metabotropic glutamate receptors in rat brain.
[Definition]

ChEBI: 2-amino-3-phosphonopropanoic acid is a non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group. It has a role as a metabotropic glutamate receptor antagonist and a human metabolite. It is a non-proteinogenic alpha-amino acid, a member of phosphonic acids and an alanine derivative.
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