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

• ChemBase ID: 34025
• Molecular Formular: C11H14N2O
• Molecular Mass: 190.24166
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
• IUPAC Traditional name: 5-methoxytryptamine; 5 methoxytryptamine
• Synonyms: 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; 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

Database IDs

• CAS Number: 608-07-1; 66-83-1
• EC Number: 210-153-7
• MDL Number: MFCD00005662
• Beilstein Number: 145587
• PubChem SID: 24883984; 24857245; 160997332
• PubChem CID: 1833
• CHEBI ID: 2089
• CHEMBL: 8165
• Chemspider ID: 1767
• IUPHAR ligand ID: 107
• KEGG ID: C05659
• Wikipedia Title: 5-Methoxytryptamine

CALCULATED PROPERTIES

• Acid pKa: 17.44662
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.6793671
• LogD (pH = 7.4): -0.9497424
• Log P: 1.3287662
• Molar Refractivity: 56.8361 cm^3
• Polarizability: 23.225039 Å^3
• Polar Surface Area: 51.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Light Brown Solid
• Melting Point: 118-120°C; 119 - 121°C; 120-122 °C; 121-123 °C; 121-123 °C(lit.); 121-123°C
• Hydrophobicity(logP): 1.444

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• Storage Warning: IRRITANT; Irritant
• RTECS: NL4059000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... HTR1A(3350), HTR2A(3356), HTR2C(3358)rat ... Htr2a(29595), Htr2c(25187), Htr7(65032)

Product Information

• Purity: ≥98.0% (NT); 95%; 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C11H14N2O
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02100847

Free Base
Off-white crystals

Sigma Aldrich - 286583

Packaging
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
Nonselective serotonin receptor agonist that lacks affinity for the 5-HT3 receptor.

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.

REFERENCES

• 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)