Aniracetam
AMpaMet · sarpul · anixiku · draganon · Anisitan · Ro 13-3057 · RO 13-5057 · ANIRACETAM
Identifiers & Physical Properties
| CAS No. | 72432-10-1 |
|---|---|
| Molecular formula | C12H13NO3 |
| Average molar mass | 219.24 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | 1.6 |
|---|---|
| Topological polar surface area | 46.6 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 2 |
| Heavy atoms | 16 |
| Formal charge | 0 |
| Complexity | 282 |
| Drugs | Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Listed in ZINC15 |
| LogP (partition coefficient) | 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 |
| Melting point | 121-122C |
| Boiling point | 399.7±34.0 °C(Predicted) |
| Density | 1.236±0.06 g/cm3(Predicted) |
| Storage conditions | Sealed in dry,Room Temperature |
| Solubility | Chloroform (Slightly), Methanol (Slightly)Soluble in chloroform. Also soluble in ethanol. Insoluble in water |
| pKa (acidity coefficient) | -1.74±0.20(Predicted) |
| Physical state | Solid |
| Color | White |
| 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 DataBase Reference | 72432-10-1(CAS DataBase Reference) |
| FDA UNII | 5L16LKN964 |
| ATC code | N06BX11 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H303 |
| GHS precautionary statements | P270-P301+P312-P403-P501c |
| Water hazard class (WGK) | 2 |
| RTECS number | UY5781900 |
| Customs code | 2933.79.1500 |
| Toxicity | LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin) |
Safety & Regulations
| GHS classification | 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%) |
| Water hazard class (WGK) | 2 |
| RTECS number | UY5781900 |
| Customs code | 2933.79.1500 |
| Toxicity | LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin) |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| GHS hazard statements | H303 |
| GHS precautionary statements | P270-P301+P312-P403-P501c |
Applications & Uses
Description
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.
Uses
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.
Preparation & Synthesis
Preparation
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.