(RS)-AMPA hydrobromide

Base Information

• Chemical Name: (RS)-AMPA hydrobromide
• CAS No.: 171259-81-7
• Molecular Formula: C7H11BrN2O4
• Molecular Weight: 267.07724
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID001017723
• ChEMBL ID: CHEMBL608555
• Mol file: 171259-81-7.mol

Synonyms:(RS)-AMPA hydrobromide;171259-81-7;118896-96-1;AMPA hydrobromide;(+/-)-AMPA hydrobromide;(RS)-AMPA (hydrobromide);2-amino-3-(5-methyl-3-oxo-1,2-oxazol-4-yl)propanoic acid;hydrobromide;2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoic acid hydrobromide;(+/-)-alpha-Amino-3-hydroxy-5-methylisoxazole- 4-propionic Acid Hydrobromide;(+/-)-alpha-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid hydrobromide;(R,S)-ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID HYDROBROMIDE;(+/-)-AMPA (hydrobromide);GNF-Pf-2579;(+/-)-AMPA;SR-01000075447;(y)-AMPA hydrobromide;(?)-AMPA hydrobromide;EU-0100581;()-AMPA (hydrobromide);()-AMPA;CHEMBL608555;SCHEMBL7200262;DTXSID001017723;Tox21_500581;AKOS015910238;AKOS040745334;CCG-221885;LP00581;NCGC00093962-01;NCGC00261266-01;( inverted question mark)-AMPA hydrobromide;A-266;FT-0605181;FT-0661850;G-017;(+/-)-AMPA hydrobromide, >=98% (HPLC);J-010703;SR-01000075447-1;SR-01000075447-4;(RS)-?-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid hydrobromide;2-AMINO-3-(3-HYDROXY-5-METHYLISOXAZOL-4-YL)PROPANOIC ACID HBR;hydrobromide.;alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid hydrobromide;4-Isoxazolepropanoic acid, alpha-amino-2,3-dihydro-5-methyl-3-oxo-, monohydrobromide;( inverted exclamation markA)-|A-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid hydrobromide;( inverted question mark)-alpha-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid hydrobromide

Chemical Property of (RS)-AMPA hydrobromide

Chemical Property:

• Melting Point: 205-208°C
• PSA: 109.58000
• LogP: 1.30140
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: ≥10mg/L
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 265.99022
• Heavy Atom Count: 14
• Complexity: 284

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R,S)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionicAcidHydrobromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)NO1)CC(C(=O)O)N.Br
• Uses: A potent and selective agonist of the 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.

Technology Process of (RS)-AMPA hydrobromide

There total 7 articles about (RS)-AMPA hydrobromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

diethyl acetamido<(3-methoxy-5-methylisoxazol-4-yl)methyl>malonate (75989-23-0) → (RS)-α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid hydrobromide (171259-81-7)

Guidance literature:

With hydrogen bromide; at 130 - 140 ℃; for 5h;

DOI:10.1002/jhet.5570340155

Reference yield:

4-hydroxymethyl-3-methoxy-5-methylisoxazole (75989-21-8) → (RS)-α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid hydrobromide (171259-81-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / thionyl chloride / benzene / 24 h / Heating

2: 1.) NaH / 1.) EtOH, 10 min, 2.) EtOH, reflux, 24 h

3: 93 percent / 48percent HBr / 5 h / 130 - 140 °C

With thionyl chloride; hydrogen bromide; sodium hydride; In benzene;

DOI:10.1002/jhet.5570340155

Reference yield:

4-(chloromethyl)-3-methoxy-5-methylisoxazole (75989-22-9) → (RS)-α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid hydrobromide (171259-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) EtOH, 10 min, 2.) EtOH, reflux, 24 h

2: 93 percent / 48percent HBr / 5 h / 130 - 140 °C

With hydrogen bromide; sodium hydride;

DOI:10.1002/jhet.5570340155

upstream raw materials:

diethyl acetamido<(3-methoxy-5-methylisoxazol-4-yl)methyl>malonate

3-Methoxy-5-methyl-isoxazol-4-carbonsaeure

4-(chloromethyl)-3-methoxy-5-methylisoxazole

4-hydroxymethyl-3-methoxy-5-methylisoxazole

Refernces

• 1、 Hansen,Krogsgaard-Larsen. "Isoxazole amino-acids as glutamic acid agonists. Synthesis of some analogues and homologues of ibotenic acid.". . p. 1826 - 1833. Retrieved 2007/10/02.