3-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-[(4-methoxyphenyl)methyl]prop-2-enamide

• ChemBase ID: 153135
• Molecular Formular: C23H27N3O2
• Molecular Mass: 377.47938
• Monoisotopic Mass: 377.21032712
• SMILES: CN(C)CCc1c[nH]c2c1cc(cc2)/C=C/C(=O)NCc1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)CNC(=O)/C=C/c1ccc2c(c1)c(CCN(C)C)c[nH]2
• InChI: InChI=1S/C23H27N3O2/c1-26(2)13-12-19-16-24-22-10-6-17(14-21(19)22)7-11-23(27)25-15-18-4-8-20(28-3)9-5-18/h4-11,14,16,24H,12-13,15H2,1-3H3,(H,25,27)
• InChIKey: LBVZWEWTNUDWNS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-[(4-methoxyphenyl)methyl]prop-2-enamide
• IUPAC Traditional name: 3-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-[(4-methoxyphenyl)methyl]prop-2-enamide
• Synonyms: 3-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-(4-methoxybenzyl)-acrylamide; GR 46611

Database IDs

• CAS Number: 185259-85-2
• MDL Number: MFCD00953517
• PubChem SID: 24278785; 162247275
• PubChem CID: 6160690

CALCULATED PROPERTIES

• Acid pKa: 15.624061
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.055841595
• LogD (pH = 7.4): 1.3173208
• Log P: 3.4484415
• Molar Refractivity: 115.2388 cm^3
• Polarizability: 44.91191 Å^3
• Polar Surface Area: 57.36 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble28 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... HTR1A(3350), HTR1B(3351), HTR1D(3352)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H27N3O2

DETAILS

Sigma Aldrich - G8543

Biochem/physiol Actions
5-HT1D serotonin receptor agonist.
Caution
Protect from light.
Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline