L-AP4 Chemical Properties

Melting point:

207-215 °C

Boiling point:

491.7±55.0 °C(Predicted)

Density 

1.628±0.06 g/cm3(Predicted)

storage temp. 

0-6°C

solubility 

H2O : 50 mg/mL (273.07 mM; Need ultrasonic)

pka

2.19±0.10(Predicted)

form 

solid

color 

White

Water Solubility 

Soluble to 5 mM in water and to 100 mM in 1eq. NaOH

Sensitive 

Light Sensitive

CAS DataBase Reference

23052-81-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

ES7191700

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

L-AP4 Usage And Synthesis

Description

Metabotropic glutamate receptors (mGluR) function to modulate excitatory synaptic transmission in the brain. Eight subtypes (1-8) and multiple splice variants of the mGluR have been identified and grouped based on their pharmacological properties. Group I mGluRs (subtypes 1 and 5) activate the phosphatidyl inositol pathway, while Group II (2 and 3) and Group III (4, 6, 7, and 8) inhibit adenylyl cyclase. L-AP4, an analog of L-glutamic acid, is a selective Group III mGluR agonist that functions presynaptically to suppress glutamate release (IC₅₀ = 2.5 μM). L-AP4 has been shown to depress synaptic transmission in glutamatergic pathways in the hippocampus, olfactory bulb, and retina as well as act as an agonist at the quisqualate-sensitized AP6 site in hippocampus.

Chemical Properties

white to off-white crystalline powder

Uses

Metabotropic glutamate receptors (mGluR) function to modulate excitatory synaptic transmission in the brain. Eight subtypes (1-8) and multiple splice variants of the mGluR have been identified and grouped based on their pharmacological properties. Group I mGluRs (subtypes 1 and 5) activate the phosphatidyl inositol pathway, while Group II (2 and 3) and Group III (4, 6, 7, and 8) inhibit adenylyl cyclase. L-AP4, an analog of L-glutamic acid, is a selective Group III mGluR agonist that functions presynaptically to suppress glutamate release (IC50 = 2.5 μM). L-AP4 has been shown to depress synaptic transmission in glutamatergic pathways in the hippocampus, olfactory bulb, and retina as well as act as an agonist at the quisqualate-sensitized AP6 site in hippocampus.

Uses

L(+)-2-Amino-4-phosphonobutanoic acid (L-AP4) is a mGluR-4/6 receptor agonist.

Definition

ChEBI: (2S)-2-amino-4-phosphonobutanoic acid is a non-proteinogenc L-alpha-amino acid that is L-alpha-aminobutyric acid in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group. It is a potent and selective agonist for the group III metabotropic glutamate receptors (mGluR4/6/7/8). It has a role as a metabotropic glutamate receptor agonist. It is a non-proteinogenic L-alpha-amino acid and a member of phosphonic acids.

Biological Activity

Selective group III metabotropic glutamate receptor agonist. Synaptic depressant. Agonist at the quisqualate-sensitized AP6 site in hippocampus. Also available as part of the Group III mGlu Receptor Tocriset™ and Mixed mGlu Receptor Tocriset™ .

storage

Room temperature

L-AP4(23052-81-5)Related Product Information

• 12AP
• 4-PHOSPHONOBUTYRIC ACID
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• (S)-2-Amino-2-methyl-4-phosphonobutanoic acid
• DL-2-AMINO-4-PHOSPHONOBUTYRIC ACID
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• ANTI-IGG, HUMAN AP CONJ
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• ANTI-IGG H AND L CHAIN, RABBIT AP CONJ,ANTI-IGG(H+L), RABBIT AP CONJ
• ANTI-IMMUNOGLOBULIN G, BOVINE, F(AB')2, AP
• ANTI-IGG H AND L CHAIN, HORSE AP CONJ
• L-AP4
• ANTI-IGG H AND L CHAIN, SHEEP AP CONJ