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

• ChemBase编号: 4164
• 分子式: C12H13NO3
• 平均质量: 219.23652
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1-(4-methoxybenzoyl)pyrrolidin-2-one
• IUPAC传统名: aniracetam; 1-(4-methoxybenzoyl)pyrrolidin-2-one
• 商标名: AMPAMET; Draganon; Sarpul
• 别名: 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

登记号

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

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 1.1055021
• LogD (pH = 7.4): 1.1055021
• Log P: 1.1055021
• 摩尔折射率: 58.9575 cm^3
• 极化性: 22.40938 Å^3
• 极化表面积: 46.61 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.55
• LOG S: -1.95
• 溶解度: 2.47e+00 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 121-122°C

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: UY5781900
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: AMPA receptor
• 相关基因信息: human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM5(2915), GRM6(2916), GRM7(2917), GRM8(2918)rat ... Gria1(50592)
• 生物活性机理: Dopamine D2 receptor agonist; Nicotinic acetylcholine (nACh) receptor agonist; Selective AMPA receptor modulator; Serotonin (5-HT2A) receptor agonist

产品相关信息

• 纯度: ≥98%
• 成盐信息: Free Base
• 应用领域: Antidepressant; Anxiolytic; Nootropic

详细说明

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.

参考文献

• 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.