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Aniracetam

Levetiracetam class brain cell metabolism drugs Pharmacological effects Pharmacokinetics Side effects Precautions Chemical Properties Uses Production methods
Aniracetam
Aniracetam structure
CAS No.
72432-10-1
Chemical Name:
Aniracetam
Synonyms
sarpul;AMpaMet;anixiku;draganon;Ro 13-3057;RO 13-5057;ANIRACETAM;Tegumetine;Anitracetam;Ro-13-5057/001
CBNumber:
CB6185499
Molecular Formula:
C12H13NO3
Formula Weight:
219.24
MOL File:
72432-10-1.mol

Aniracetam Properties

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)
FDA UNII
5L16LKN964
SAFETY
  • Risk and Safety Statements
Hazard statements  H303
WGK Germany  2
RTECS  UY5781900
Toxicity LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin)

Aniracetam price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A9950 Aniracetam ≥98% 72432-10-1 50mg $131 2020-08-18 Buy
Sigma-Aldrich A9950 Aniracetam ≥98% 72432-10-1 250mg $504 2018-11-20 Buy
TCI Chemical A2394 Aniracetam >98.0%(GC) 72432-10-1 1g $65 2021-03-22 Buy
TCI Chemical A2394 Aniracetam >98.0%(GC) 72432-10-1 5g $218 2021-03-22 Buy
Alfa Aesar J61661 Aniracetam 72432-10-1 1g $85.8 2021-03-22 Buy

Aniracetam Chemical Properties,Uses,Production

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%.

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.

Chemical Properties

Crystalline Solid

Originator

Roche (Switzerland)

Uses

cognitive enhancer

Uses

Cognition enhancer related to Piracetam. Nootropic.

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.]

Aniracetam Preparation Products And Raw materials

Raw materials

Preparation Products


Aniracetam Suppliers

Global( 319)Suppliers
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Hubei Langyou International Trading Co., Ltd
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View Lastest Price from Aniracetam manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-22 Aniracetam
72432-10-1
US $1.00 / KG 1KG 99% 100 Jinan Ande Pharmaceutical Co.,Ltd.
2021-10-22 Aniracetam
72432-10-1
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-10-21 Aniracetam
72432-10-1
US $1.00 / g 1000g 99% 20ton/month Wuhan Aoliqisi New Material Technology Co., Ltd.

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