Aniracetam 72432-10-1 No1 producer in China CAS NO.72432-10-1

Levetiracetam class brain cell metabolism drugs Pharmacological effects Pharmacokinetics Adverse reactions Precautions Chemical Properties Application Production methods
Product Name: Aniracetam
Synonyms: 1-(4-methoxybenzoyl)-2-pyrrolidinon;1-(p-methoxybenzoyl)-2-pyrrolidinon;1-p-anisoyl-2-pyrrolidinone;draganon;sarpul;1-(4-METHOXYBENZOYL)-2-PYRROLIDINONE;ANIRACETAM;RO 13-5057
CAS: 72432-10-1
MF: C12H13NO3
MW: 219.24
EINECS:
Product Categories: Glutamate;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Smart drug;Nootropic
Mol File: 72432-10-1.mol

【Product Name】

1-(4-Methoxybenzoyl)-2-pyrrolidinone
【Synonyms】

1-(4-Methoxybenzoyl)-2-pyrrolidinone
1-(4-Methoxybenzoyl)pyrrolidin-2-one
1-p-Anisoyl-2-pyrrolidinone
Draganon
Ro-13-5057
Sarpul
【CAS】

72432-10-1
【Formula】

C12H13NO3
【Molecular Weight】

219.24
【RTECS】

UY5781900
【Merck】

12,700
【Beilstein/Gmelin】

4807205
Physical and Chemical Properties Back to Contents
【Appearance】

White solid.
【Solubility in water】

3.3 g/L
【Melting Point】

121 - 122
【Boiling Point】

400
【Vapor Pressure】

1.3E-6 (25 C)
【Density】

1.24 g/cm3 (20 C)
【pKa/pKb】

15.74 (pKb)
【Partition Coefficient】

.27
【Heat Of Vaporization】

65.05 kJ/mol
【Usage】

Has shown potential as an anxiolytic.

Aniracetam Usage And Synthesis
Levetiracetam class brain cell metabolism drugs Aniracetam, also known as aniracetam, together with piracetam and nefiracetam, belong to the same class of piracetam metabolized drugs of brain cells. 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.
Pharmacological effects Aniracetam, a cyclized derivative of γ- aminobutyric acid, can improve the brain function. It can selectively exert effect on central nervous system through penetration into blood-brain barrier. It can activate the metabolism activity of brain cell and protect the nerve cells. This product can also promote the intelligence by affecting the glutamate receptor system. Moreover, it improves skin’s resistance to hypoxia, preventing the occurrence of malfunction of learning and memory caused by a variety of chemical substances, hypercapnia, scopolamine and electrical shock. This product has no sedative or excitation effect. Animal experiments show that this product promotes the memory recovery in normal rats’ learning process. It can fight against hypoxia-induced memory recession and relieve the memory malfunction caused by certain reasons.
[Indications] It is used for the treatment of mild or moderate malfunction of learning, memory and cognition in vascular dementia and Alzheimer's disease. It can also be used for treating memory recession after stroke, memory defect in old people and children who undergo development retardation.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
Pharmacokinetics According to literature, it is rapidly absorbed after oral administration by rats. The plasma concentration reaches highest level within 20 to 40 minutes. The drug is mainly distributed in the gastrointestinal tract, kidney, liver, brain and blood. After 24 hours, 77% to 85% is excreted out through urine, 4% from faeces. Major metabolite in urine is N-p-anisoyl-aminobutyric acid and 5-hydroxy-2-pyrrolidone.
Human: After oral administration, half-life of blood Plains drug elimination averages at 20 to 30 minutes. Plasma concentration becomes undetectable after two hours.
Adverse reactions This product has fewer adverse reactions, occasionally dry mouth, anorexia, constipation, dizziness, and drowsiness. They disappear after stopping taking the drug.
Precautions 1. Adjust the dose for patients of liver dysfunction.
2. It can deteriorate the symptoms of Huntington's chorea.
3. Patients who is allergic to this drug or other pyrrolidone-class drugs are not allowed.
4. Safety range: 0.3 ~ 1.8g / d.
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.