| Identification | Back 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 Properties | Back 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) | [color ]
White to off-white |
| Hazard Information | Back 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is a non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group.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. | [in vivo]
DL-AP3 (4?mg/kg, ?i.p., for 5?weeks) with SKF81297 (1?mg/kg, ?i.p.) reduces the hyperactivity phenotype in Fmr1 KO mice[3].
DL-AP3 (4.0-12.0 mg/animal, i.c.v. infusion, 100 μL) blocks development of visceral pain symptoms and neuroendocrinological changes in the blood plasma of sheep[4].
| Animal Model: | Fmr1 KO mice[3] | | Dosage: | 4?mg/kg with SKF81297 (1?mg/kg) | | Administration: | i.p., for 5?weeks. | | Result: | Reduced the distance traveled by Fmr1 KO mice (open-field test).
Reduced the swim latency on the final day in the Fmr1 KO mice (Morris Water Maze test).
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| Animal Model: | Sheep with visceral pain evoked by colonic distension (CD)[4] | | Dosage: | 4.0-12.0 mg/animal | | Administration: | i.c.v. infusion, 100 μL | | Result: | Decreased intensity from appearance of clinical signs of visceral pain caused by CD test.
Diminished the increase of plasma cortisol, E, NE and DA concentrations caused by visceral pain provoked by CD episode.
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| [IC 50]
mGluR 1; mGluR 5 |
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