methyl N-[3-(2-acetamidoethyl)-1H-indol-5-yl]carbamate

• ChemBase ID: 153181
• Molecular Formular: C14H17N3O3
• Molecular Mass: 275.30308
• Monoisotopic Mass: 275.12699142
• SMILES: CC(=O)NCCc1c[nH]c2c1cc(cc2)NC(=O)OC
• Canonical SMILES: COC(=O)Nc1ccc2c(c1)c(CCNC(=O)C)c[nH]2
• InChI: InChI=1S/C14H17N3O3/c1-9(18)15-6-5-10-8-16-13-4-3-11(7-12(10)13)17-14(19)20-2/h3-4,7-8,16H,5-6H2,1-2H3,(H,15,18)(H,17,19)
• InChIKey: MPZVHKLZCUEJFO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-[3-(2-acetamidoethyl)-1H-indol-5-yl]carbamate
• IUPAC Traditional name: methyl N-[3-(2-acetamidoethyl)-1H-indol-5-yl]carbamate
• Synonyms: N-[3-[2-(Acetylamino)ethyl]-1H-indol-5-yl]carbamic Acid Methyl Ester; 5-MCA-NAT; GR 135531; 5-Methoxycarbonylamino-N-acetyltryptamine; 5-Methoxycarbonylamino-N-acetyltryptamine; GR 135531

Database IDs

• CAS Number: 190277-13-5
• MDL Number: MFCD00672678
• PubChem SID: 24724487; 162247320
• PubChem CID: 4284525

CALCULATED PROPERTIES

• Acid pKa: 12.954511
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.1622853
• LogD (pH = 7.4): 1.1622844
• Log P: 1.1622856
• Molar Refractivity: 76.3033 cm^3
• Polarizability: 29.670958 Å^3
• Polar Surface Area: 83.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1,4-Dioxane; DMSO: soluble ~28 mg/mL; H2O: insoluble; Methanol; THF,
• Apperance: Brown Foam; off-white solid
• Melting Point: 68-70°C

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Safety Statements: 22-24/25

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C14H17N3O3

DETAILS

Sigma Aldrich - G0294

Biochem/physiol Actions
MT3 melatonin receptor agonist.
Caution
Desiccate.
Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline