Aniracetam 72432-10-1 1-(4-methoxybenzoyl)-2-pyrrolidinon
Chemical Properties | Crystallization from ethanol, m.p. 12l ~ 122 °C. Acute toxicity LD50 for rat, mouse (mg / kg): 4500,> 5000 oral. |
Application |
1. Piracetam derivative, a improvement agent for γ-lactam brain function. Selectively exert effect on the brain system, promote and enhance memory function. Compared with Piracetam, it has a stronger effect, faster onset of action, and lower toxicity. Used for improving brain function, especially treating the behavioral and mental disorders for sequela patients of senile dementia, cerebrovascular disease. 2. It is a γ-lactam-class agent of improving brain function. It can exert on the brain tissue through penetrating the blood-brain barrier, and improve brain function and memory. |
Production methods |
Method 1: Reflux the reaction mixture of 2- pyrrolidone and methoxy benzoyl chloride at 0~10 °C in ether and in the presence of triethylamine for three hours to get the Aniracetam. Method 2: Perform the reaction between p-methoxy benzoic acid and thionyl chloride to get the methoxy benzoyl chloride (yield 90%). Then perform the reaction between methoxybenzoyl chloride and 4-aminobutyric acid in an aqueous solution of sodium hydroxide and in the presence of benzyl triethyl ammonium salt (of TEBA) to get 4- (4-methoxybenzoyl) amino butyric acid (yield 69.4%). Then have cyclization reaction in the presence of toluene and thionyl chloride to get aniracetam, yield 80.4%, mp 118 ~ 120 °C. Method 3: Methoxybenzoic acid is chloridized as post-methoxy benzoyl chloride first. Then it is reacted together with Sodium 2-pyrrolidone in tetrahydrofuran and 4-dimethylaminopyridine (DMAP) to obtain the aniracetam yield 76.2% (Take account of p-methoxy benzoyl chloride), the melting point of 118 ~ 119 °C. Method 4: 2-pyrrolidone was refluxed 1 hour in toluene containing sodium methoxide first. Then methanol was totally evaporated. Add TEBA at 10 °C, Titrate a toluene solution of p-anisoyl chloride and stir them at room temperature for 0.5h. Then stirred at 50 °C for 6h to obtain the aniracetam of 85% yield (take account of 2-pyrrolidone), melting point 120 ~ 121 °C. Method 5: 2-pyrrolidinone and triethylamine is mixed at 0 ~ 10 °C first. Then perform titration of chlorotrimethylsilane for 2 h reaction at room temperature. Add the dioxane solution of Methoxybenzoyl chloride and stir 2h at 40 °C to obtain aniracetam, yield 65%. |
Chemical Properties | Crystalline Solid |
Usage | cognitive enhancer |
Usage | Cognition enhancer related to Piracetam. Nootropic. |
Biological Activity | Nootropic, with modulatory actions through allosteric potentiation of AMPA specific receptors, reduction of glutamate receptor desensitization and potentiation of metabotropic glutamate receptor activity. Anxiolytic following systemic administration. |
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