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Aniracetam

Basic information Levetiracetam class brain cell metabolism drugs Pharmacological effects Pharmacokinetics Side effects Precautions Chemical Properties Uses Production methods Safety Related Supplier

Aniracetam Basic information

Product Name:
Aniracetam
CAS:
72432-10-1
MF:
C12H13NO3
MW:
219.24
EINECS:
615-758-3
Mol File:
72432-10-1.mol
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Aniracetam Chemical Properties

Melting point:
121-122?C
Boiling point:
399.7±34.0 °C(Predicted)
Density 
1.236±0.06 g/cm3(Predicted)
storage temp. 
Store at RT
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)
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Safety Information

WGK Germany 
2
RTECS 
UY5781900
Toxicity
LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin)

MSDS

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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.

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.

brand name

Draganon; Sarpul;Ampamet; Reset

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.]

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AniracetamSupplierMore

Shanghai Everchem Co., Ltd Gold
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86-29-81325371
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info@everchem.cn
JX NUTRITIONAL CHEMICAL CO., LIMITED Gold
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86-21-66278832
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sales@jxnutritionalchemical.com
J & K SCIENTIFIC LTD.
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010-82848833- ;010-82848833-
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jkinfo@jkchemical.com;market6@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
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21-61259100-
Email:
sh@meryer.com
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel:
86-21-50328103 * 801、802、803、804 Mobile:18930552037
Email:
3bsc@sina.com
Basic information Levetiracetam class brain cell metabolism drugs Pharmacological effects Pharmacokinetics Side effects Precautions Chemical Properties Uses Production methods Safety Related Supplier