(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate

• ChemBase编号: 153858
• 分子式: C20H23N3O2
• 平均质量: 337.41552
• 单一同位素质量: 337.17902699
• SMILES: C[C@@]12CCN([C@@H]1N(c1c2cc(cc1)OC(=O)Nc1ccccc1)C)C
• Canonical SMILES: O=C(Nc1ccccc1)Oc1ccc2c(c1)[C@]1(C)CCN([C@@H]1N2C)C
• InChI: InChI=1S/C20H23N3O2/c1-20-11-12-22(2)18(20)23(3)17-10-9-15(13-16(17)20)25-19(24)21-14-7-5-4-6-8-14/h4-10,13,18H,11-12H2,1-3H3,(H,21,24)/t18-,20+/m1/s1
• InChIKey: PBHFNBQPZCRWQP-QUCCMNQESA-N

名称和登记号

名称

• IUPAC标准名: (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate
• IUPAC传统名: (3aS,8aR)-1,3a,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate
• 别名: (-)-N-Phenylcarbamoyleseroline; 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester); Phenserine

登记号

• CAS号: 101246-66-6
• MDL号: MFCD00672748
• PubChem SID: 162247997
• PubChem CID: 192706

理论计算性质

• 质子供体: 1
• LogD (pH = 5.5): 3.1347353
• LogD (pH = 7.4): 4.18858
• Log P: 4.2501016
• 摩尔折射率: 99.9552 cm^3
• 极化性: 37.64495 Å^3
• 极化表面积: 44.81 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true
• Acid pKa: 12.859102
• 质子受体: 4

分子性质

理化性质

• 溶解度: DMSO: >5 mg/mL; H2O: <2 mg/mL
• 外观: off-white solid

安全信息

• RTECS编号: UY8586000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H23N3O2

详细说明

Sigma Aldrich - P0111

Biochem/physiol Actions
(-)-Phenserine, a phenylcarbamate derivative, is a selective, non-competitive inhibitor of acetylcholinesterase (AChE). (-)-Phenserine produces rapid, potent, and long-lasting AChE inhibition, in vivo. It is significantly less toxic than (-)-physostigmine. (-)-Phenserine improves cognitive performance in both young learning-impaired and elderly rats. Reduced secretion of β-amyloid (Abeta) has been observed in cell lines exposed to (-)-phenserine, occurring through translational regulation of β-amyloid precursor protein (beta-APP) mRNA via a non-cholinergic mechanism. These in vitro findings appear to translate in vivo into animal models and humans.