N-[2-(2-bromo-5-methoxy-1H-indol-3-yl)ethyl]acetamide

• ChemBase ID: 60151
• Molecular Formular: C13H15BrN2O2
• Molecular Mass: 311.1744
• Monoisotopic Mass: 310.03168973
• SMILES: c1(c(c2c([nH]1)ccc(c2)OC)CCNC(=O)C)Br
• Canonical SMILES: COc1ccc2c(c1)c(CCNC(=O)C)c([nH]2)Br
• InChI: InChI=1S/C13H15BrN2O2/c1-8(17)15-6-5-10-11-7-9(18-2)3-4-12(11)16-13(10)14/h3-4,7,16H,5-6H2,1-2H3,(H,15,17)
• InChIKey: FNHLXIXCQDGUCQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(2-bromo-5-methoxy-1H-indol-3-yl)ethyl]acetamide
• IUPAC Traditional name: N-[2-(2-bromo-5-methoxy-1H-indol-3-yl)ethyl]acetamide
• Synonyms: N-[2-(2-Bromo-5-methoxy-1H-indol-3-yl)ethyl]acetamide; N-Acetyl-2-bromo-5-methoxytryptamine; NSC 674637; 2-Bromo Melatonin; N-[2-(2-Bromo-5-methoxy-1H-indol-3-yl)ethyl]-acetamide

Database IDs

• CAS Number: 142959-59-9
• MDL Number: MFCD01076464
• PubChem SID: 162025892
• PubChem CID: 126731

CALCULATED PROPERTIES

• Acid pKa: 14.138614
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.6167208
• LogD (pH = 7.4): 1.6167208
• Log P: 1.6167209
• Molar Refractivity: 73.6847 cm^3
• Polarizability: 29.395294 Å^3
• Polar Surface Area: 54.12 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol; Water
• Apperance: Yellow Solid
• Melting Point: 138-140°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

DETAILS

Toronto Research Chemicals - B684500

A melatonin agonist with high affinity for chicken brain membrane melatonin receptors (Ki=0.031nM) in a comptetition radioligand binding assay using 2-[125I]iodomelatonin.

REFERENCES

• Spandoni, G., et al.: J. Med. Chem., 36, 25, 4069 (1993)