2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

• ChemBase编号: 34025
• 分子式: C11H14N2O
• 平均质量: 190.24166
• 单一同位素质量: 190.11061308
• SMILES: [nH]1cc(c2c1ccc(c2)OC)CCN
• Canonical SMILES: NCCc1c[nH]c2c1cc(OC)cc2
• InChI: InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
• InChIKey: JTEJPPKMYBDEMY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
• IUPAC传统名: 5-methoxytryptamine; 5 methoxytryptamine
• 别名: 5-甲氧基色胺; 3-(2-氨基乙基)-5-甲氧基吲哚; 5-甲基羟色胺; 甲氧色胺; O-甲氧基色胺; 5-Methoxytryptamine; 2-(5-Methoxyindol-3-yl)ethylamine; 3-(2-Aminoethyl)-5-methoxyindole; 5-Methoxyindole-3-ethanamine; 5-MOT; Deacetylmelatonin; NSC 56422; 5-Methoxytryptamine; 2-(5-Methoxy-1H-indol-3-yl)ethanamine; 2-(5-methoxy-1H-indol-3-yl)ethan-1-amine; 5-METHOXYTRYPTAMINE FREE BASE; Mexamine; O-Methylserotonin; 2-(5-Methoxy-1H-indol-3-yl)ethylamine; 5-Methoxytryptamine; 3-(2-Aminoethyl)-5-methoxy-1H-indole; 2-(5-Methoxy-1H-indol-3-yl)ethanamine; 2-[5-(Methyloxy)-1H-indol-3-yl]ethanamine; 5-Methoxy-1H-indole-3-ethanamine; [2-(5-Methoxy-1H-indol-3-yl)ethyl]amine; Methoxytryptamine

登记号

• CAS号: 608-07-1; 66-83-1
• EC号: 210-153-7
• MDL号: MFCD00005662
• Beilstein号: 145587
• PubChem SID: 24883984; 160997332; 24857245
• PubChem CID: 1833
• CHEBI ID: 2089
• CHEMBL: 8165
• Chemspider ID: 1767
• IUPHAR配体索引: 107
• KEGG ID: C05659
• 维基百科标题: 5-Methoxytryptamine

理论计算性质

• Acid pKa: 17.44662
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): -1.6793671
• LogD (pH = 7.4): -0.9497424
• Log P: 1.3287662
• 摩尔折射率: 56.8361 cm^3
• 极化性: 23.225039 Å^3
• 极化表面积: 51.04 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; DMSO; Methanol
• 外观: Light Brown Solid
• 熔点: 118-120°C; 119 - 121°C; 120-122 °C; 121-123 °C; 121-123 °C(lit.); 121-123°C
• 疏水性(logP): 1.444

安全信息

• 保存条件: 2-8°C; Refrigerator
• 保存注意事项: IRRITANT; Irritant
• RTECS编号: NL4059000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 相关基因信息: human ... HTR1A(3350), HTR2A(3356), HTR2C(3358)rat ... Htr2a(29595), Htr2c(25187), Htr7(65032)

产品相关信息

• 纯度: ≥98.0% (NT); 95%; 97%; 98%
• 级别: purum
• Empirical Formula (Hill Notation): C11H14N2O
• 分类: Genuine Natural Compounds

详细说明

MP Biomedicals - 02100847

Free Base
Off-white crystals

Sigma Aldrich - 286583

包装
1 g in glass bottle
100 mg in glass bottle
Application
Reactant for preparation of:
• Carboline disaccharide domain of shishijimicin A1
• Melatonin analogs for the reduction of intraocular pressure2
• 5-HT4 receptor ligands3
• inhibitors of sortase A and isocitrate lyase4
• Therapeutic agents for treatment of ischemia/reperfusion (I/R) injury5
• Aurora and epidermal growth factor receptor kinase inhibitors6
• Agents for the treatment of human papillomavirus infection7
• Manzamine analogues for the control of neuroinflammation and cerebral infections8
• Inhibitors of pro-inflammatory cytokines9
• Tacrine-melatonin hybrids as multifunctional agents for alzheimer′s disease10

Sigma Aldrich - 65372

Biochem/physiol Actions
非选择性血清素受体激动剂，不具有 5-HT3 受体亲和性。

Toronto Research Chemicals - M271695

A tryptamine derivative that is closely related to the neurotransmitter Melatonin (M215000) and Serotonin (S274980). It acts as a full agonist at the 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors but has no affinity for the 5-HT3 receptor.

参考文献

• Yamada, J. et al.: Eur. J. Pharmacol., 323, 235 (1997)
• Craig, D.A. et al.: NAun. Schmied. Arch. Pharmacol., 342, 9 (1997)
• Hemedah, M. et al.: Br. J. Pharmacol., 126, 179 (1997)
• Millan-Plano, S. et al.: Int. J. Mol. Sci., 11, 312 (1997)