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

• ChemBase ID: 4164
• Molecular Formular: C12H13NO3
• Molecular Mass: 219.23652
• Monoisotopic Mass: 219.08954328
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 72432-10-1
• MDL Number: MFCD00153767
• PubChem SID: 24277955; 46506607; 160967596
• PubChem CID: 2196

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.1055021
• LogD (pH = 7.4): 1.1055021
• Log P: 1.1055021
• Molar Refractivity: 58.9575 cm^3
• Polarizability: 22.40938 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.55
• LOG S: -1.95
• Solubility (Water): 2.47e+00 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 121-122°C

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: UY5781900
• German water hazard class: 2
• 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: Dopamine D2 receptor agonist; Nicotinic acetylcholine (nACh) receptor agonist; Selective AMPA receptor modulator; Serotonin (5-HT2A) receptor agonist

Product Information

• Purity: ≥98%
• Salt Data: Free Base
• Application(s): Antidepressant; Anxiolytic; Nootropic

DETAILS

MP Biomedicals - 02193613

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

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

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, ,

Sigma Aldrich - A9950

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

Toronto Research Chemicals - A672800

Cognition enhancer related to Piracetam. Nootropic.

REFERENCES

• 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.