CAS 77521-29-0

α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid

Description:

α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid, commonly known as AMPA, is a synthetic amino acid and a potent agonist of the glutamate receptor, specifically the AMPA subtype. It plays a crucial role in synaptic transmission and plasticity in the central nervous system. AMPA is characterized by its ability to enhance excitatory neurotransmission, making it significant in various neurological processes, including learning and memory. The compound features a unique isoxazole ring structure, which contributes to its biological activity. It is soluble in water and exhibits stability under physiological conditions. AMPA is often used in research to study synaptic function and is also of interest in the development of drugs targeting neurological disorders. Its pharmacological properties include rapid onset and short duration of action, which are essential for its role in mediating fast excitatory signals in the brain. However, excessive activation of AMPA receptors can lead to excitotoxicity, highlighting the importance of regulatory mechanisms in maintaining neuronal health.

Formula: C₇H₁₀N₂O₄

InChI: InChI=1S/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)

InChI key: InChIKey=UUDAMDVQRQNNHZ-UHFFFAOYSA-N

SMILES: C(C(C(O)=O)N)C=1C(=O)NOC1C

Synonyms:

• (R,S)-alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
• (R,S)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
• (RS)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
• (±)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
• 2-Amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoic acid
• 2-Amino-3-(5-methyl-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)propanoic acid
• 2-Amino-3-(5-methyl-3-oxo-2,3-dihydroisoxazol-4-yl)propanoic acid
• 3-(5-Methyl-3-Oxo-2,3-Dihydro-1,2-Oxazol-4-Yl)Alanine
• 3-(5-methyl-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)-L-alanine
• 4-Isoxazolepropanoic acid, alpha-amino-2,3-dihydro-5-methyl-3-oxo-
• 4-Isoxazolepropanoic acid, α-amino-2,3-dihydro-5-methyl-3-oxo-
• <span class="text-smallcaps">D</smallcap>,<smallcap>L</span>-α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid
• AMPA (pharmaceutical)
• D,L-alpha-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid
• alpha-Amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid
• alpha-Amino-2,3-dihydro-5-methyl-3-oxoisoxazolepropionic acid
• alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
• dl-alpha-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid
• dl-α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid
• gamma-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid
• α-Amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid
• α-Amino-2,3-dihydro-5-methyl-3-oxoisoxazole-4-propionic acid
• α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionate
• α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid
• γ-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid

4-Isoxazolepropanoic acid, a-amino-2,3-dihydro-5-methyl-3-oxo-

CAS: 77521-29-0

Formula: C₇H₁₀N₂O₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 186.1653

Ref: IN-DA01CBOJ

(RS)-AMPA

CAS: 77521-29-0

Formula: C₇H₁₀N₂O₄

Purity: ≥ 99.0%

Color and Shape: White solid

Molecular weight: 186.17

Ref: 7W-GL5388

3-(3-Hydroxy-5-methylisoxazol-4-yl)-DL-alanine

CAS: 77521-29-0

3-(3-Hydroxy-5-methylisoxazol-4-yl)-DL-alanine

Purity: ≥95%

Color and Shape: White To Off White Powder

Molecular weight: 186.17g/mol

Ref: 54-OR1150T

(R,S)-a-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

CAS: 77521-29-0

Stability Hygroscopic
Applications A potent and selective agonist of the putative, excitatory neurotransmitter L-glutamic acid. AMPA does not interfere with binding sites for kainic acid in vitro, and AMPA- induced neuronal excitation is not significantly affected by NMDA antagonists.
References Krogsgaard-Larsen, et al.: Nature, 284, 64 (1980), Honore, T., et al.: J. Neurochem., 38, 173 (1982), MacDonald, J.F., et al.: Science, 253, 1132 (1991)

Formula: C₇H₁₀N₂O₄

Color and Shape: Neat

Molecular weight: 186.17

Ref: TR-A611500

AMPA

Controlled Product

CAS: 77521-29-0

Applications AMPA is the definitive agonist of the AMPA glutamatergic ionotropic receptor.

Formula: C₇H₁₀N₂O₄

Color and Shape: White To Off-White

Molecular weight: 186.17

Ref: TR-A634293

3-(3-Hydroxy-5-methylisoxazol-4-yl)-DL-alanine

CAS: 77521-29-0

M01253 - 3-(3-Hydroxy-5-methylisoxazol-4-yl)-DL-alanine

Formula: C₇H₁₀N₂O₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 186.167

Ref: 10-M01253

(RS)-AMPA

CAS: 77521-29-0

(RS)-AMPA ((±)-AMPA) is a glutamate analog. (RS)-AMPA is an agonist of effective and selective excitatory neurotransmitter L-glutamic acid.

Formula: C₇H₁₀N₂O₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 186.17

Ref: TM-T16800