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72432-10-1 molecular structure
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1-(4-methoxybenzoyl)pyrrolidin-2-one

ChemBase ID: 4164
Molecular Formular: C12H13NO3
Molecular Mass: 219.23652
Monoisotopic Mass: 219.08954328
SMILES and InChIs

SMILES:
O=C1N(CCC1)C(=O)c1ccc(OC)cc1
Canonical SMILES:
COc1ccc(cc1)C(=O)N1CCCC1=O
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

Cite this record

CBID:4164 http://www.chembase.cn/molecule-4164.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-(4-methoxybenzoyl)pyrrolidin-2-one
IUPAC Traditional name
aniracetam
1-(4-methoxybenzoyl)pyrrolidin-2-one
Brand Name
AMPAMET
Draganon
Sarpul
Synonyms
Aniracetam
Ro 13-3057
Ro 13-5057/001
1-P-ANISOYL-2-PYRROLIDINONE
Aniracetam
Draganon
Sarpul
Ampamet
Ro 13-5057
1-(4-Methoxybenzoyl)-2-pyrrolidinone
Reset
Sarpol
CAS Number
72432-10-1
MDL Number
MFCD00153767
PubChem SID
46506607
24277955
160967596
PubChem CID
2196

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.1055021  LogD (pH = 7.4) 1.1055021 
Log P 1.1055021  Molar Refractivity 58.9575 cm3
Polarizability 22.40938 Å3 Polar Surface Area 46.61 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 0.55  LOG S -1.95 
Solubility (Water) 2.47e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
121-122°C expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
UY5781900 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Target
AMPA receptor expand Show data source
Gene Information
human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM5(2915), GRM6(2916), GRM7(2917), GRM8(2918)rat ... Gria1(50592) expand Show data source
Mechanism of Action
Dopamine D2 receptor agonist expand Show data source
Nicotinic acetylcholine (nACh) receptor agonist expand Show data source
Selective AMPA receptor modulator expand Show data source
Serotonin (5-HT2A) receptor agonist expand Show data source
Purity
≥98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Antidepressant expand Show data source
Anxiolytic expand Show data source
Nootropic expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02193613 external link
Reported to increase ion conductance through AMPA receptors, and also involve the cholinergic system.
DrugBank - DB04599 external link
Item Information
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
Selleck Chemicals - S1281 external link
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, ,
Sigma Aldrich - A9950 external link
Biochem/physiol Actions
Cognition enhancer (nootropic) that potentiates AMPA receptor mediated ion conductance and potentiates metabotropic glutamate receptor activity.
Toronto Research Chemicals - A672800 external link
Cognition enhancer related to Piracetam. Nootropic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Toide, Arch. Int. Pharmacodyn. , 298 : 25 (1989).
  • • 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
  • • http://en.wikipedia.org/wiki/Aniracetam
  • • Foltyn, P., et al.: Arzneim.-Forsch., 33, 865 (1983)
  • • Yamada, K., et al.: Pharmacol. Biochem. Behav., 22, 645 (1983)
  • • Schlappi, B., et al.: Drug Invest., 5, 50 (1983)
  • • 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:
  • • 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.
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PATENTS

PATENTS

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