アニラセタム
ドラガノン · サープル · 1-(4-メトキシベンゾイル)ピロリジン-2-オン · アニラセタム · サルプル · アミダセダン · 1-(4-メトキシベンゾイル)-2-ピロリドン · アニラセタム (JAN)
識別子と物理属性
| CAS No. | 72432-10-1 |
|---|---|
| 分子式 | C12H13NO3 |
| 平均分子量 | 219.24 g/mol |
| 単同位体質量 | 219.08954328 g/mol |
| SMILES | COc1ccc(C(=O)N2CCCC2=O)cc1 |
| InChIKey | ZXNRTKGTQJPIJK-UHFFFAOYSA-N |
| PubChem CID | 2196 |
| ChEMBL | CHEMBL36994 |
| ChEBI | CHEBI:47943 |
| EC No. | 615-758-3 |
| DTXSID | DTXSID5045128 |
| 現地名 | アニラセタム |
化学・物理的性質
| XLogP | 1.6 |
|---|---|
| 極性表面積 | 46.6 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 2 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 282 |
| 医薬品 | Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Listed in ZINC15 |
| LogP（分配係数） | 0.93 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Collision Cross Section | 145.49 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]146.6 Ų [M+H]+ [CCS Type: TW |
| 融点 | 121-122C |
| 沸点 | 399.7±34.0 °C(Predicted) |
| 密度 | 1.236±0.06 g/cm3(Predicted) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 溶解度 | クロロホルム（微量）、メタノール（微量）クロロホルムに可溶。エタノールにも可溶。水に不溶 |
| pKa（酸解離定数） | -1.74±0.20(Predicted) |
| 外観・状態 | 個体 |
| 色 | 白い |
| Merck | 14,662 |
| InChI | InChI=1S/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 |
| SMILES | N1(C(=O)C2=CC=C(OC)C=C2)CCCC1=O |
| CAS データベース | 72432-10-1(CAS DataBase Reference) |
化学的特性
Aniracetam is a white or colorless solid. It has a molecular structure that consists of an organic compound with a methoxy group attached to one side of a benzene ring, and a carboxylic acid group attached to the other side. It forms crystals when dissolved in ethanol, and has a melting point of 121-122°C. Exhibits acute toxicity in rats and mice, with LD50 values of approximately 4500mg/kg and >5000mg/kg when administered orally.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.WarningH361 (66.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Repr. 2 (66.7%) |
| 水環境危害等級（WGK） | 2 |
| RTECS 番号 | UY5781900 |
| 毒性 | LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin) |
| 税関コード | 2933.79.1500 |
用途
説明
Aniracetam, also known as N-anisoyl-2-pyrrolidinone, together with piracetam and nefiracetam, belong to the same class of piracetam metabolized drugs of brain cells. It is a non-NMDA receptor agent useful for the treatment of cognitive impairment. 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. It is well tolerated and efficacious in improving velocity and accuracy of the saccades, complex reaction time, and other aspects of performance.
使用
Aniracetam is AMPA receptor potentiator with Cognition enhancer related to Piracetam. It is used as a nootropic drug to ameliorate memory and attention disturbances accompanying cerebrovascular diseases and degenerative brain disorders. Compound with anti-depressive properties used as a mental performance enhancer. Slows the rate of ion-channel closing.
製法・合成法
製造方法
Aniracetam is prepared by condensing 2-pyrrolidone with 4-methoxybenzoyl chloride. The drug was first made in the 1970s by Hoffmann-La Roche. This piracetam-related cognition enhancer reduces glutamate receptor desensitization.
純化方法
Purify aniracetam by recrystallisation from EtOH. It is a nootropic (Alzheimer) drug. [Gouliaev & Senning Brain Research Rev 19 180 1994.]