Aniracetam

HCID 2196CAS 72432-10-1
Substructure searchFind similar structures

Basic information

Standard SMILES
COc1ccc(C(=O)N2CCCC2=O)cc1
InChIKey
ZXNRTKGTQJPIJK-UHFFFAOYSA-N
Molecular formula
C12H13NO3
Average molar mass
219.24 g/mol
Monoisotopic mass
219.08954328

Overview

Aniracetam is a N-acylpyrrolidine and a member of pyrrolidin-2-ones.

Names & identifiers

Preferred name
Aniracetam
IUPAC
1-(4-methoxybenzoyl)pyrrolidin-2-one
English name
Aniracetam
Molecular formula
C12H13NO3
Molecular weight
219.24

Names & synonyms

aniracetam72432-10-1DraganonSarpul1-(4-Methoxybenzoyl)-2-pyrrolidinoneRo 13-50571-p-Anisoyl-2-pyrrolidinoneRo-13-50571-anisoyl-2-pyrrolidinone1-p-anisoylpyrrolidin-2-oneDTXSID5045128NSC-758223
Show more names
AMpaMetanixikuAnisitanRo 13-3057TegumetineAnitracetam
5L16LKN964Ro-135057DTXCID3025128CHEBI:479431-[(4-methoxyphenyl)carbonyl]pyrrolidin-2-one1-((4-methoxyphenyl)carbonyl)pyrrolidin-2-oneaniracetamumRefChem:558129

Database identifiers

CAS
72432-10-1
PubChem CID
2196
DTXSID
DTXSID5045128
ChEMBL
CHEMBL36994
ChEBI
CHEBI:47943
UNII
5L16LKN964
EC Number
615-758-3
Nikkaji
J18.602C

Properties

Computed structural properties

XLogP
1.6
Topological polar surface area
46.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
16

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Pharmaceuticals -> Listed in ZINC15

LogP0.93
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section · 2 items

145.49 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

146.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
121 · 121-122C
Boiling point
399.7 · 399.7±34.0 °C(Predicted)
Density
1.236 · 1.236±0.06 g/cm3(Predicted)
storage temp.
Sealed in dry,Room Temperature
solubility
Chloroform (Slightly), Methanol (Slightly)
pka
-1.74 · -1.74±0.20(Predicted)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H361 (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 information

Hazard Classes and CategoriesRepr. 2 (66.7%)

Safety data

wgk
2
rtecs
UY5781900
hs_code
2933.79.1500
Toxicity
LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin)
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

PharmacodynamicsAniracetam possesses a wide range of anxiolytic properties, which may be mediated by an interaction between cholinergic, dopaminergic and serotonergic systems.
Biological Half-Life1-2.5 hours
MeSH Pharmacological Classification · 2 items

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms.

Applications · 2 items

DescriptionAniracetam, 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.

UsesAniracetam 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 methods

PreparationAniracetam 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.

Upstream & downstream products

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东科立康药业有限公司053-88113608 17854192669
合肥翰刚医药科技有限公司+8618062405514 · [email protected]

Additional notes

DefinitionChEBI: Aniracetam is a member of pyrrolidin-2-ones and a N-acylpyrrolidine with anti-depressive properties used as a mental performance enhancer.

Related reactions

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Linked notes

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