ethyl 5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylate

• ChemBase ID: 15877
• Molecular Formular: C13H15NO3
• Molecular Mass: 233.2631
• Monoisotopic Mass: 233.10519335
• SMILES: c1(c(n(c2c1cc(cc2)O)C)C)C(=O)OCC
• Canonical SMILES: Cc1c(C(=O)OCC)c2c(n1C)ccc(c2)O
• InChI: InChI=1S/C13H15NO3/c1-4-17-13(16)12-8(2)14(3)11-6-5-9(15)7-10(11)12/h5-7,15H,4H2,1-3H3
• InChIKey: YTBNTDMBGXAOCG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylate
• IUPAC Traditional name: ethyl 5-hydroxy-1,2-dimethylindole-3-carboxylate; ethyl 5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylate
• Synonyms: Ethyl 5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylate; Dimecarbine; Mecarbinate; Mecarbinate; 5-Hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid ethyl ester

Database IDs

• CAS Number: 15574-49-9
• MDL Number: MFCD00451373
• PubChem SID: 160979184
• PubChem CID: 616236

CALCULATED PROPERTIES

• Acid pKa: 9.491993
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.551921
• LogD (pH = 7.4): 2.548487
• Log P: 2.5519648
• Molar Refractivity: 65.9457 cm^3
• Polarizability: 25.926277 Å^3
• Polar Surface Area: 51.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 211 - 213°C
• Partition Coefficient: 2.931
• Hydrophobicity(logP): 3.448

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Target: Others
• Mechanism of Action: Serotonin release regulator

Product Information

• Purity: 95%; 95+%
• Salt Data: Free Base
• Application(s): Antihypertensive agent

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 152A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 676C, (ir)
• Fr. Pat., 1967, M5142, (synth, pharmacol)
• Bell, M.R. et al., J. Med. Chem., 1967, 10, 264, (synth, bibl)
• Kucklaender, U., Tetrahedron, 1972, 28, 5251, (synth)
• Macor, J.E. et al., Tet. Lett., 1989, 30, 2509, (synth)