CAS 72432-10-1|Sarpul|1-(4-methoxybenzoyl)pyrrolidin-2-one|Aniracetam|1-(4-methoxybenzoyl)pyrrolidin-2-one|Draganon|1-P-ANISOYL-2-PYRROLIDINONE|AMPAMET|1-(4-Methoxybenzoyl)-2-pyrrolidinone|Ro 13-505...

General Information

Structure

Molecular Formula

C₁₂H₁₃NO₃

Molecular Mass

219.23652

Exact Mass

219.08954328

Charge

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

Canonic Smiles

COc1ccc(cc1)C(=O)N1CCCC1=O

Isomeric Smiles

O=C1N(CCC1)C(=O)c1ccc(OC)cc1

Calculated Properties

JChem

LogD (pH = 7.4)

1.11

LogD (pH = 5.5)

1.11

Log P

1.11

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-4.79

Polar Surface Area

46.61

Polarizability

22.87

Molar Refractivity

58.96

LOG S

-2.44

Data Source

Names and Identifiers

IUPAC Traditional name

1-(4-methoxybenzoyl)pyrrolidin-2-one aniracetam

Synonyms

Aniracetam1-P-ANISOYL-2-PYRROLIDINONERo 13-50571-(4-Methoxybenzoyl)-2-pyrrolidinoneDraganonSarpulAmpametAniracetamRo 13-5057/001SarpolResetRo 13-30571-p-anisoylpyrrolidin-2-one1-(4-METHOXYBENZOYL)-2-PYRROLIDINONEAniracetamaniracetam

IUPAC name

1-(4-methoxybenzoyl)pyrrolidin-2-one

Brand Name

SarpulDraganonAMPAMET

Names and Identifiers

Registration numbers

CAS Number

72432-10-1

MDL Number

MFCD00153767

PubChem SID

242779554650660716096759646530484

PubChem CID

2196

MetaboLights Database

MTBLS2096MTBLS1622

SureChEMBL Database

SCHEMBL70998

CHEMBL

CHEMBL36994

CHEBI ID

CHEBI:31223CHEBI:47943CHEBI:40102

ACToR Database

72432-10-1

Drug Central Database

Protein Data Bank

LINCS Database

CompTox Database

DrugBank ID

Patent number

EP1356812WO2007137227US2006276462

Beilstein Number

KEGG ID

PDBeChem Database

KEGG DRUG Database

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

Room Temperature (15-30°C)

Refrigerator

RTECS

UY5781900

MSDS Link

Download link

German water hazard class

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

Target

AMPA receptor

Gene Information

human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM5(2915), GRM6(2916), GRM7(2917), GRM8(2918)rat ... Gria1(50592)

Mechanism of Action

Selective AMPA receptor modulator

Serotonin (5-HT2A) receptor agonist

Nicotinic acetylcholine (nACh) receptor agonist

Dopamine D2 receptor agonist

Physical Property

Apperance

White Solid

Melting Point

121-122°C

Solubility

Chloroform

Methanol

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S1281

Research Area: Neurological Disease
Biological Activity:
Aniracetam is an ampakine and nootropic of the racetam chemical class purported to be considerably more potent than piracetam. It selectively modulates the AMPA receptor. It is lipid soluble and has possible cognition enhancing effects. It has been tested in animals extensively, Alzheimer’s patients and temporarily-impaired healthy subjects. It has shown potential as an anxiolytic in three clinical animal models. [1]References on Aniracetam[1] http://en.wikipedia.org/wiki/Aniracetam, ,

MP Biomedicals

02193613

Reported to increase ion conductance through AMPA receptors, and also involve the cholinergic system.

Sigma Aldrich

A9950

Biochem/physiol Actions
Cognition enhancer (nootropic) that potentiates AMPA receptor mediated ion conductance and potentiates metabotropic glutamate receptor activity.

DrugBank

DB04599

Drug Groups

experimental

Description

Compound with anti-depressive properties used as a mental performance enhancer.

Pharmacology

Aniracetam possesses a wide range of anxiolytic properties, which may be mediated by an interaction between cholinergic, dopaminergic and serotonergic systems.

Affected Organisms

Humans and other mammals

Half Life

1-2.5 hours

References

• Nakamura K, Kurasawa M: Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43. [Pubmed]

• Lawrence JJ, Brenowitz S, Trussell LO: The mechanism of action of aniracetam at synaptic alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors: indirect and direct effects on desensitization. Mol Pharmacol. 2003 Aug;64(2):269-78. [Pubmed]

External Links

• [Wikipedia]

TRC

A672800

Cognition enhancer related to Piracetam. Nootropic.

Molecule Details

References

PubChem Literature

From Data Sources

• Nakamura K, Kurasawa M: Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43. Pubmed

• http://en.wikipedia.org/wiki/Aniracetam

• Toide, Arch. Int. Pharmacodyn. , 298 : 25 (1989).

• Yamada, K., et al.: Pharmacol. Biochem. Behav., 22, 645 (1983)

• Schlappi, B., et al.: Drug Invest., 5, 50 (1983)

• Foltyn, P., et al.: Arzneim.-Forsch., 33, 865 (1983)

• indirect and direct effects on desensitization. Mol Pharmacol. 2003 Aug;64(2):269-78.

• 2. Nakamura K, Kurasawa M. Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43.

• 1. Lawrence JJ, Brenowitz S, Trussell LO: The mechanism of action of aniracetam at synaptic alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors:

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

1-(4-methoxybenzoyl)pyrrolidin-2-one aniracetam

Synonyms

IUPAC name

1-(4-methoxybenzoyl)pyrrolidin-2-one

Brand Name

SarpulDraganonAMPAMET

Registration numbers

CAS Number

72432-10-1

MDL Number

MFCD00153767

PubChem SID

242779554650660716096759646530484

PubChem CID

2196

MetaboLights Database

MTBLS2096MTBLS1622

SureChEMBL Database

SCHEMBL70998

CHEMBL

CHEMBL36994

CHEBI ID

CHEBI:31223CHEBI:47943CHEBI:40102

ACToR Database

72432-10-1

Drug Central Database

Protein Data Bank

LINCS Database

CompTox Database

DrugBank ID

Patent number

EP1356812WO2007137227US2006276462

Beilstein Number

KEGG ID

PDBeChem Database

KEGG DRUG Database

Properties

Safety Information

Storage Condition

-20°C

Room Temperature (15-30°C)

Refrigerator

RTECS

UY5781900

MSDS Link

Download link

German water hazard class

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

Target

AMPA receptor

Gene Information

human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM5(2915), GRM6(2916), GRM7(2917), GRM8(2918)rat ... Gria1(50592)

Mechanism of Action

Selective AMPA receptor modulator

Serotonin (5-HT2A) receptor agonist

Nicotinic acetylcholine (nACh) receptor agonist

Dopamine D2 receptor agonist

Physical Property

Apperance

White Solid

Melting Point

121-122°C

Solubility

Chloroform

Methanol

Molecule Details

Selleck Chemicals

S1281

MP Biomedicals

02193613

Reported to increase ion conductance through AMPA receptors, and also involve the cholinergic system.

Sigma Aldrich

A9950

Biochem/physiol Actions
Cognition enhancer (nootropic) that potentiates AMPA receptor mediated ion conductance and potentiates metabotropic glutamate receptor activity.

DrugBank

DB04599

Drug Groups

experimental

Description

Compound with anti-depressive properties used as a mental performance enhancer.

Pharmacology

Aniracetam possesses a wide range of anxiolytic properties, which may be mediated by an interaction between cholinergic, dopaminergic and serotonergic systems.

Affected Organisms

Humans and other mammals

Half Life

1-2.5 hours

References

• Nakamura K, Kurasawa M: Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43. [Pubmed]

External Links

• [Wikipedia]

TRC

A672800

Cognition enhancer related to Piracetam. Nootropic.

References

PubChem Literature

From Data Sources

• Nakamura K, Kurasawa M: Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43. Pubmed

• http://en.wikipedia.org/wiki/Aniracetam

• Toide, Arch. Int. Pharmacodyn. , 298 : 25 (1989).

• Yamada, K., et al.: Pharmacol. Biochem. Behav., 22, 645 (1983)

• Schlappi, B., et al.: Drug Invest., 5, 50 (1983)

• Foltyn, P., et al.: Arzneim.-Forsch., 33, 865 (1983)

• indirect and direct effects on desensitization. Mol Pharmacol. 2003 Aug;64(2):269-78.

• 2. Nakamura K, Kurasawa M. Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43.

• 1. Lawrence JJ, Brenowitz S, Trussell LO: The mechanism of action of aniracetam at synaptic alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors:

Bioactivity

PubChem BioAssay

Molecule

ID:4164