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72432-10-1

72432-10-1 Structure

72432-10-1 Structure
IdentificationMore
[Name]

Aniracetam
[CAS]

72432-10-1
[Synonyms]

1-(4-METHOXYBENZOYL)-2-PYRROLIDINONE
ANIRACETAM
RO 13-5057
1-(4-methoxybenzoyl)-2-pyrrolidinon
1-(p-methoxybenzoyl)-2-pyrrolidinon
1-p-anisoyl-2-pyrrolidinone
draganon
sarpul
2-PYRROLIDINONE,1-(4-METHOXYBENZOYL)
1-(4-Methoxybenzoyl)-2-pyrrolidinone, Ro 13-5057
1-(4-Methoxybenzoyl)pyrrolidin-2-one
Ro-13-5057/001
[EINECS(EC#)]

615-758-3
[Molecular Formula]

C12H13NO3
[MDL Number]

MFCD00153767
[Molecular Weight]

219.24
[MOL File]

72432-10-1.mol
Chemical PropertiesBack Directory
[Melting point ]

121-122?C
[Boiling point ]

399.7±34.0 °C(Predicted)
[density ]

1.236±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

-1.74±0.20(Predicted)
[Water Solubility ]

Soluble in chloroform. Also soluble in ethanol. Insoluble in water
[Merck ]

14,662
[InChIKey]

ZXNRTKGTQJPIJK-UHFFFAOYSA-N
[CAS DataBase Reference]

72432-10-1(CAS DataBase Reference)
Safety DataBack Directory
[WGK Germany ]

2
[RTECS ]

UY5781900
[Toxicity]

LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin)
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Thionyl chloride-->1,4-Dioxane-->4-Dimethylaminopyridine-->Chlorotrimethylsilane-->4-Aminobutyric acid-->2-Pyrrolidinone-->Anisic acid-->4-Methoxybenzoyl chloride-->Triethylamine-->1-TRIMETHYLSILYL-2-PYRROLIDINONE-->Sodium hydride
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

1-(4-Methoxybenzoyl)-2-pyrrolidinone(72432-10-1).msds
Hazard InformationBack Directory
[Description]

Aniracetam is a non-NMDA receptor agent useful for the treatment of cognitive impairment. In a clinical study, it showed good to very good improvement in 60% of patients with cerebral insufficiency. Statistically significant improvement in the psychobehavioral parameters has been observed in a group of patients with senile dementia of the Alzheimer’s type. Aniracetam is well tolerated and efficacious in improving velocity and accuracy of the saccades, complex reaction time, and other aspects of performance compared with placebo group in hypoxic volunteers. Its nootropic property has been attributed to the cholinergic blockade.
[Originator]

Roche (Switzerland)
[Manufacturing Process]

40.0 g of p-methoxybenzoyl chloride, 25.0 g of 2-pyrrolidinone and 110 ml of absolute diethyl ether are treated at between 0°C and 10°C while stirring with 52.5 ml of triethylamine. The mixture is stirred at room temperature for a further 30 minutes and at reflux for 3 hours, then cooled down and treated at 2°C with cold water. The insoluble constituents are filtered off under suction and washed with water and diethyl ether. The thus obtained solid substance is recrystallized from alcohol after drying over phosphorus pentoxide. There is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone which melts at 121°-122°C.
[Brand name]

Draganon; Sarpul;Ampamet; Reset
[Therapeutic Function]

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.
[Purification Methods]

Purify aniracetam by recrystallisation from EtOH. It is a nootropic (Alzheimer) drug. [Gouliaev & Senning Brain Research Rev 19 180 1994.]
Questions And AnswerBack Directory
[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.
[Side effects]

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.
[Uses]

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%.
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

72432-10-1(sigmaaldrich)
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