Aniracetam

Base Information

• Chemical Name: Aniracetam
• CAS No.: 72432-10-1
• Molecular Formula: C12H13NO3
• Molecular Weight: 219.24
• NSC Number: 758223
• UNII: 5L16LKN964
• DSSTox Substance ID: DTXSID5045128
• Nikkaji Number: J18.602C
• Wikipedia: Aniracetam
• Wikidata: Q417630
• NCI Thesaurus Code: C65236
• Metabolomics Workbench ID: 52471
• ChEMBL ID: CHEMBL36994
• Mol file: 72432-10-1.mol

Synonyms:1-(4-methoxybenzoyl)-2-pyrrolidinone;1-anisoyl-2-pyrrolidinone;aniracetam;Ro 13-5057;Ro-13-5057

Chemical Property of Aniracetam

Chemical Property:

• Appearance/Colour: White Crystalline or Crystalline Powde
• Vapor Pressure: 1.34E-06mmHg at 25°C
• Melting Point: ?58°C(lit.)
• Refractive Index: 1.573
• Boiling Point: 399.7 °C at 760 mmHg
• PKA: -1.74±0.20(Predicted)
• Flash Point: 195.5 °C
• PSA: 46.61000
• Density: 1.236 g/cm³
• LogP: 1.39570
• Storage Temp.: Store at RT
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in chloroform. Also soluble in ethanol. Insoluble in water
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 219.08954328
• Heavy Atom Count: 16
• Complexity: 282

Purity/Quality:

99.89% ^*data from raw suppliers

Aniracetam ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(=O)N2CCCC2=O
• Recent ClinicalTrials: A Clinical Study to Evaluate the Efficacy of Four Supplements on Improving Readiness for Intimacy
• Description: Aniracetam, also known as N-anisoyl-2-pyrrolidinone, together with piracetam and nefiracetam, belong to the same class of piracetam metabolized drugs of brain cells. It is a non-NMDA receptor agent useful for the treatment of cognitive impairment. These drugs can enhance the activity of synaptic neurons phospholipase, increase the ATP formation and transport in brain, increase protein synthesis and RNA, promote the usage of brain on amino acids, phospholipids, glucose and oxygen, increase the patient's response, excitability and memory. Aniracetam has a higher effect than piracetam, but with a relatively minor side effect. It is well tolerated and efficacious in improving velocity and accuracy of the saccades, complex reaction time, and other aspects of performance.
• Uses: Aniracetam is AMPA receptor potentiator with Cognition enhancer related to Piracetam. It is used as a nootropic drug to ameliorate memory and attention disturbances accompanying cerebrovascular diseases and degenerative brain disorders. Compound with anti-depressive properties used as a mental performance enhancer. Slows the rate of ion-channel closing.
• Therapeutic Function: Nootropic

Technology Process of Aniracetam

There total 16 articles about Aniracetam 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%

2-pyrrolidinon (616-45-5) + 4-Methoxybenzyl alcohol (105-13-5) → aniracetam (72432-10-1)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; 9-azanoradamantane N-oxyl; oxygen; copper(l) chloride; In tetrahydrofuran; at 23 ℃; for 2h; Time; Molecular sieve;

DOI:10.1039/c8sc01410h

Reference yield: 91.0%

2-pyrrolidinon (616-45-5) + 4-methoxybenzoic acid (100-09-4) → aniracetam (72432-10-1)

Guidance literature:

With silica gel; In toluene; Concentration; Reagent/catalyst; Reflux;

Reference yield: 89.0%

carbon monoxide (201230-82-2) + 4-methoxy-N-prop-2-enylbenzamide (66897-25-4) → aniracetam (72432-10-1)

Guidance literature:

With bis[2-(diphenylphosphino)phenyl] ether; palladium(II) iodide; In toluene; at 105 ℃; for 20h; under 37503.8 Torr; regioselective reaction; Inert atmosphere; Autoclave;

DOI:10.1002/anie.201503954

upstream raw materials:

1-(4-methoxybenzoyl)pyrrolidine

2-pyrrolidinon

4-methoxy-benzoyl chloride

pyrographite

Downstream raw materials:

4-methoxy-N-(2-methoxybenzyl)benzamide

4-methoxy-N-phenylbenzamide

N-[4-hydroxybenzoyl]pyrrolidin-2-one

Anisamidobutyric acid

Refernces

• 1、 -. "Catalytic synthesis method of Aniracetam". Paragraph 0058; 0059; 0061; 0062; 0063-0073. . Retrieved 2019/05/08.
• 2、 -. "Method for catalytically oxidizing amine to be synthesized into amide through dipyridyl-type manganese catalyst". Paragraph 0017-0027; 0052-0054. . Retrieved 2019/06/30.