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

Product Name
(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST
CAS No.
5652-28-8
Chemical Name
(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST
Synonyms
2-AP3;Alanine, 3-phosphono-;2-Amino-3-phosphonopropionic acid;(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST
CBNumber
CB5503036
Molecular Formula
C3H8NO5P
Formula Weight
169.07
MOL File
5652-28-8.mol
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(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST Property

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
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Safety

HS Code 
2931499090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
13852
Product name
DL-AP3
Purity
≥95%
Packaging
50mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
13852
Product name
DL-AP3
Purity
≥95%
Packaging
100mg
Price
$68
Updated
2024/03/01
TRC
Product number
A627553
Product name
DL-2-Amino-3-phosphonopropionicAcid(AP3)
Packaging
100mg
Price
$75
Updated
2021/12/16
TRC
Product number
A627553
Product name
DL-2-Amino-3-phosphonopropionicAcid(AP3)
Packaging
250mg
Price
$160
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
38685
Product name
DL-2-Amino-3-phosphonopropionic acid
Packaging
250mg
Price
$650
Updated
2021/12/16
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(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST Chemical Properties,Usage,Production

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).
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.

IC 50

mGluR 1; mGluR 5

References

[1] DARRYLE D. SCHOEPP  James A M  David E Jane. Pharmacological agents acting at subtypes of metabotropic glutamate receptors[J]. Neuropharmacology, 1999, 38 10: Pages 1431-1476. DOI: 10.1016/s0028-3908(99)00092-1
[2] JON E. HAWKINSON  Paul L W  Manuel Acosta Burruel. The metabotropic glutamate receptor antagonist l-2-amino-3-phosphonopropionic acid inhibits phosphoserine phosphatase[J]. European journal of pharmacology, 1996, 307 2: Pages 219-225. DOI: 10.1016/0014-2999(96)00253-1
[3] S OTANI  W B L  J A Connor. Long-term potentiation and evidence for novel synaptic association in CA1 stratum oriens of rat hippocampus.[J]. Learning & memory, 1995, 2 2: 101-106. DOI: 10.1101/lm.2.2.101
[4] HAO LI  Gang H  Jian Hua Ding. Group I mGluR ligands fail to affect 6-hydroxydopamine- induced death and glutamate release of PC12 cells.[J]. Acta Pharmacologica Sinica, 2003, 24 7: 641-645.
[5] ZHAO-HUI XU. Group I mGluR antagonist rescues the deficit of D1-induced LTP in a mouse model of fragile X syndrome.[J]. Molecular Neurodegeneration, 2012, 7: 24. DOI: 10.1186/1750-1326-7-24

(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST Preparation Products And Raw materials

Raw materials

Preparation Products

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(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST Suppliers

China 20 India 1 Switzerland 1 United States 2 Global 24
Shanghai EFE Biological Technology Co., Ltd.
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ChemeGen(Shanghai) Biotechnology Co.,Ltd.
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Shanghai Maclean Biochemical Technology Co., LTD
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Shanghai Tachizaki Biomedical Research Center
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5652-28-8, (+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONISTRelated Search:

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  • (+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST
  • 2-Amino-3-phosphonopropionic acid
  • 2-AP3
  • Alanine, 3-phosphono-
  • 5652-28-8