Aniracetam Aniracetam
aniracetam
CAS: 72432-10-1
Molecular Formula: C12H13NO3
Aniracetam Aniracetam - Names and Identifiers
| Name | aniracetam |
| Synonyms | anixiku AMpaMet Ro 13-3057 aniracetam Aniracetam Aniracetam 1-p-anisoyl-2-pyrrolidinone 1-(p-methoxybenzoyl)-2-pyrrolidinon 1-(4-methoxybenzoyl)-2-pyrrolidinon 1-(4-methoxybenzoyl)-2-pyrrolidinone 1-(4-methoxybenzoyl)pyrrolidin-2-one |
| CAS | 72432-10-1 |
| EINECS | 615-758-3 |
| InChI | InChI=1/C12H13NO3/c1-16-10-6-4-9(5-7-10)12(15)13-8-2-3-11(13)14/h4-7H,2-3,8H2,1H3 |
| InChIKey | ZXNRTKGTQJPIJK-UHFFFAOYSA-N |
Aniracetam Aniracetam - Physico-chemical Properties
| Molecular Formula | C12H13NO3 |
| Molar Mass | 219.24 |
| Density | 1.236±0.06 g/cm3(Predicted) |
| Melting Point | 121-122?C |
| Boling Point | 399.7±34.0 °C(Predicted) |
| Flash Point | 195.5°C |
| Water Solubility | Soluble in chloroform. Also soluble in ethanol. Insoluble in water |
| Solubility | Chloroform (Slightly), Methanol (Slightly) |
| Vapor Presure | 1.34E-06mmHg at 25°C |
| Appearance | Solid |
| Color | White |
| Merck | 14,662 |
| pKa | -1.74±0.20(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.573 |
| Physical and Chemical Properties | Crystals from ethanol, melting point 12l ~ 122 °c. Acute toxicity LD50 rats, mice (mg/kg): about 4500,>5000 Oral. |
| Use | Gamma lactam brain function improving agent, can act on the brain tissue through the blood-brain barrier, improve brain function, improve memory |
Aniracetam Aniracetam - Risk and Safety
| WGK Germany | 2 |
| RTECS | UY5781900 |
| Toxicity | LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin) |
Aniracetam Aniracetam - Standard
Authoritative Data Verified Data
This product is 1-(4-methoxybenzoyl)-2-pyrrolidone. The content of C12H13N03 shall be between 98.0% and 102.0% based on the dry product.
Last Update：2024-01-02 23:10:35
Aniracetam Aniracetam - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Odorless.
- This product is soluble in chloroform, soluble in acetone or ethyl acetate, slightly soluble in anhydrous ethanol, insoluble in water.
melting point
The melting point of this product (General rule 0612) is 118-122°C.
absorption coefficient
take an appropriate amount of this product and weigh it accurately, add anhydrous ethanol to dissolve and quantitatively dilute to prepare a solution containing about 10ug per lml, according to ultraviolet-visible spectrophotometry (General rule 0401), the absorbance was measured at a wavelength of 282nm, and the absorption coefficient was 476 to 506.
Last Update：2022-01-01 13:38:29
Aniracetam Aniracetam - Differential diagnosis
Authoritative Data Verified Data
- take about 50mg of this product, put it in a test tube, add 2ml sulfuric acid to dissolve, the solution is pale yellow, add 2ml water, add several drops of sodium nitrite solution, shake for 10~15 minutes, generate white precipitate.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 769).
Last Update：2022-01-01 13:38:29
Aniracetam Aniracetam - Exam
Authoritative Data Verified Data
Related substances
take about 10 mg of this product, add mobile phase to dissolve and dilute to make a solution containing 1 mg per 1 ml, as a test solution; Take appropriate amount with precision, A solution containing 2ug per 1 ml was prepared as a control solution by quantitative dilution with mobile phase. The detection wavelength was 254nm according to the chromatographic conditions under the content measurement. Take 10 u1 of the test solution and the control solution respectively, inject the human liquid chromatograph, record the chromatogram to 4 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.2% ) , the sum of each impurity peak area shall not be greater than 5 times (1.0%) of the main peak area of the control solution.
residual solvent
take about 0.lg of this product, weigh it accurately, put it in a 20ml headspace bottle, add lml of N,N-dimethylformamide to dissolve it, seal it, shake it well, and use it as a test solution; respectively take the appropriate amount of ethanol, toluene, precision weighing, plus N,N-dimethylformamide quantitative dilution into each lml respectively containing ethanol 500ug, toluene 89ug solution, precision take lml, A 20ml headspace bottle was placed, sealed, and used as a control solution. According to the determination method of residual solvent (General Principle 0861 second method), the capillary column with 6% cyanopropyl phenyl-94% dimethyl polysiloxane as stationary liquid (or similar polarity) is the column; The initial temperature is 40°C, hold for 5 minutes, ramp to 160°C at a rate of 20°C per minute for 5 minutes at a detector temperature of 240°C. The inlet temperature was 220°C; The headspace bottle equilibration temperature was 100°C and the equilibration time was 30 minutes. Take the reference solution into the headspace, record the chromatogram, and the separation degree between the ethanol peak and the toluene peak should meet the requirements. The test solution and the reference solution were injected by Headspace, and the chromatograms were recorded. According to the external standard method to calculate the peak area, the residual amount of ethanol and toluene should be in accordance with the provisions.
loss on drying
taking this product, using phosphorus pentoxide as desiccant, drying under reduced pressure at 60°C for 4 hours, the weight loss shall not exceed 0.5% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Heavy metals
take the residue left by the ignition residue item, check according to law (General Principles 0821 second law), containing heavy metals shall not exceed 10 parts per million.
Last Update：2022-01-01 13:38:30
Aniracetam Aniracetam - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
silica gel bonded with eighteen alkyl silane was used as the filler; Acetonitrile-water (35:65) was used as the mobile phase; The detection wavelength was 283nm. Take aniracetam 50mg, put it in a 50ml Cuvette, add methanol 5ml, place it in a 70°C water bath and heat it for 1 hour, let it cool, dilute it with mobile phase to make a solution containing 1 mg per 1 ml, lOul injection liquid chromatograph, record chromatogram, aniracetam peak and degradation product peak (relative retention time is about 0.88) separation degree should meet the requirements. The number of theoretical plates is not less than 1500 based on the aniracetam peak.
assay
take an appropriate amount of this product, precision weigh, add mobile phase to dissolve and quantitatively dilute to prepare a solution containing 0.08mg per lml, as a test solution, take 10 u1 for precision measurement, inject into liquid chromatograph, record chromatogram; Take aniracetam control., same method determination. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 13:38:31
Aniracetam Aniracetam - Category
Authoritative Data Verified Data
drugs for improving brain function.
Last Update：2022-01-01 13:38:32
Aniracetam Aniracetam - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 13:38:32
Aniracetam Aniracetam - Aniracetam Capsules
Authoritative Data Verified Data
This product contains aniracetam (C12H13NO3) should be labeled the amount of 93.0% to 107.0%.
trait
The content of this product is white or white powder.
identification
- take an appropriate amount of the content of this product (about 50mg of aniracetam), add 5ml of chloroform, shake, filter, the filtrate is evaporated on a water bath, and the residue is identified under aniracetam (1) the test showed the same response.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
- Related Substances: take an appropriate amount of the contents of this product (about 10 mg equivalent to aniracetam), dissolve it with mobile phase and dilute it to prepare a solution containing 1 mg of aniracetam per 1 ml, and filter it, the filtrate was used as a test solution; An appropriate amount was taken in a precise amount and quantitatively diluted with a mobile phase to prepare a solution containing 5ug of aniracetam per 1 ml as a control solution. The detection wavelength was 254nm according to the chromatographic conditions under the content measurement. Take 10 u1 of the test solution and the control solution respectively, inject the human liquid chromatograph, record the chromatogram to 4 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.5% ) , the sum of each impurity peak area shall not be greater than 2 times (1.0%) of the main peak area of the control solution.
- dissolution dissolution of this product, according to the dissolution and release determination method (General rule 0931 The first method), hydrochloric acid solution (9-100) as the dissolution medium, the speed is rpm, operate according to law, after 45 minutes, take 20ml of the solution, filter, take 5ml of the filtrate with precision, put it in a 50ml measuring flask, dilute it to the scale with dissolution medium, shake well, measure absorbance at the wavelength of 282nm according to UV-visible spectrophotometry (General rule 0401); Take appropriate amount of aniracetam reference substance and add appropriate amount of ethanol to dissolve, A solution containing about 10ug per 1 ml was prepared by dissolving and quantitatively diluting with the dissolution medium, and the absorbance was measured by the same method to calculate the dissolution amount of each particle. The limit is 80% of the labeled amount and shall be in accordance with the provisions.
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; Acetonitrile-water (35:65) as mobile phase; The detection wavelength was 283nm. Take aniracetam 50mg, put it in a 50ml Cuvette, add methanol 5ml, place it in a 70°C water bath and heat it for 1 hour, let it cool, dilute it with mobile phase to make a solution containing 1 mg per 1 ml, 10u1 injection liquid chromatograph, record chromatogram, aniracetam peak and degradation product peak (relative retention time is about 0.88) separation degree should meet the requirements. The number of theoretical plates is not less than 1500 based on the aniracetam peak.
- the appropriate amount of the content under the difference item of the device was measured, accurately weighed, dissolved and quantitatively diluted with mobile phase to prepare a solution containing 0.08mg of aniracetam per 1 ml, filtered, the continuous filtrate was taken as the test solution, and 10ul of the sample was accurately measured. The liquid chromatograph was injected and the chromatogram was recorded, the mobile phase was added to dissolve and quantitatively dilute to prepare a solution containing 0.08mg per 1 ml, which was determined by the same method. According to the external standard method to calculate the peak area, that is.
category
Same as aniracetam.
specification
(1)0.lg (2)0.2g
storage
light shielding, sealed storage.
Last Update：2022-01-01 13:38:33
Aniracetam Aniracetam - Reference Information
| laciracetam-like brain cell metabolism drug | aniracetam, also known as aniracetam, nafeacetam belongs to the class of brain cell metabolism drugs, which can enhance the activity of phospholipase in neuronal synapses, increase the formation and transport of ATP in the brain, and increase the synthesis of protein and RNA, promotes brain utilization of amino acids, phospholipids, glucose, and oxygen, and increases patient responsiveness, excitability, and memory. Aniracetam is more potent than piracetam, with mild adverse effects. |
| pharmacological action | aniracetam is a cyclized derivative of γ-aminobutyric acid, which is a drug for improving brain function. Selectively affects the central nervous system through the blood-brain barrier. It has an activating effect on the metabolism of brain cells and a protective effect on nerve cells. This product can also produce nootropic effect by affecting the glutamate receptor system. Can improve the cortical anti-hypoxia ability, prevent by a variety of chemicals, hypercapnia, scopolamine or electric shock caused by learning, memory loss. This product has no sedative or Excitatory effect, and also has no vasodilator effect. Animal experiments show that this product has a good promoting effect on the memory reproduction process of normal rats, can resist the memory impairment caused by hypoxia, and can effectively improve the memory impairment caused by some reasons. [indications] clinical for the treatment of mild and moderate learning, memory and cognitive dysfunction in vascular dementia and Alzheimer's disease. It is also used for memory impairment after stroke, benign memory impairment in the elderly and delayed brain development in children. |
| pharmacokinetics | It is reported in the literature that the absorption is rapid after oral administration in rats, and the blood concentration can reach the peak value in 20~40 minutes. The drug is mainly distributed in the gastrointestinal tract, kidney, liver, brain and blood. After 24 hours, 77% ~ 85% from the urine, 4% from the feces. The main metabolites in urine are N-p-methoxybenzoylaminobutyric acid and 5-hydroxy-2-pyrrolidone. Human Body: After oral absorption, the elimination half-life of the original drug in blood is 20~30 minutes on average, and the blood drug concentration is difficult to measure after 2 hours. |
| adverse reactions | This product has few adverse reactions, such as dry mouth, anorexia, constipation, dizziness and drowsiness, the drug was discontinued and disappeared. |
| precautions | (1) patients with obvious abnormal liver function should adjust the dosage appropriately. (2) This product can aggravate Huntington's Chorea Symptoms. (3) allergic to this product or other pyrrolidone drugs can not be tolerated by the disabled. (4) the recommended safe use range is 0.3 ~ 1.8g/d. |
| uses | piracetam derivatives, gamma-lactam brain function improvers, selectively acting on the brain system, promote and enhance memory function. Compared with piracetam, it has the advantages of strong effect, rapid onset and low toxicity. For improving brain function, especially in patients with senile dementia, cerebrovascular disease sequelae of behavior and Mental Disorder. It is a gamma lactam brain function improving agent, which can act on brain tissue through blood-brain barrier, improve brain function and improve memory. |
| production method | Method 1: 2-pyrrolidone and p-methoxybenzoyl chloride in diethyl ether in the presence of triethylamine, reflux at 0~10 ℃ for 3H, aniracetam. Method 2: P-methoxybenzoic acid was reacted with thionyl chloride to give P-methoxybenzoyl chloride (yield 90%). Then p-methoxybenzoyl chloride was reacted with 4-aminobutyric acid in an aqueous solution of sodium hydroxide in the presence of triethylbenzylammonium salt (TEBA) to give 4-(4-methoxybenzoyl) aminobutyric acid (yield 69.4%), then, the product was cyclized in toluene in the presence of dichlorosulfoxide to obtain aniracetam with a yield of 80.4% and a melting point of 118-120 °c. Method 3: P-methoxybenzoic acid was chlorinated to p-methoxybenzoyl chloride, and then reacted with 2-pyrrolidone sodium in tetrahydrofuran in the presence of 4-dimethylaminopyridine (DMAP), yield 76.2% (based on p-methoxybenzoyl chloride), melting point 118-119 °c. Method 4: 2-pyrrolidone was refluxed in toluene containing sodium methoxide for 1H, and then methanol was distilled off. TEBA was added at 10 °c and a solution of p-methoxybenzoyl chloride in toluene was added dropwise and stirred at room temperature for 0.5h and then at 50 °c for 6h. The treatment gave aniracetam in 85% yield (based on 2-pyrrolidone) with a melting point of 120-121 °c. Method 5: 2-pyrrolidone and triethylamine were mixed, and chlorotrimethylsilane was added dropwise at 0-10 °c. The reaction was completed at room temperature for 2H. The dioxane solution of p-methoxybenzoyl chloride was added and stirred at 40 °c for 2H to obtain aniracetam in 65% yield. |
Last Update：2024-04-10 22:29:15
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