1-{[2-(2H3)methyl(2H6)propan-2-yl]amino}-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate

• ChemBase ID: 162698
• Molecular Formular: C23H28N2O3
• Molecular Mass: 380.48002
• Monoisotopic Mass: 380.20999277
• SMILES: c1cc(c2c(c1)[nH]c(c2)C)OCC(OC(=O)c1ccccc1)CNC(C)(C)C
• Canonical SMILES: O=C(c1ccccc1)OC(COc1cccc2c1cc([nH]2)C)CNC(C)(C)C
• InChI: InChI=1S/C23H28N2O3/c1-16-13-19-20(25-16)11-8-12-21(19)27-15-18(14-24-23(2,3)4)28-22(26)17-9-6-5-7-10-17/h5-13,18,24-25H,14-15H2,1-4H3
• InChIKey: UUOJIACWOAYWEZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]amino}-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate
• IUPAC Traditional name: 1-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]amino}-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate
• Synonyms: 1-[(1,1-Dimethylethyl-d9)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-2-propanol 2-Benzoate; (±)-1-[(1,1-Dimethylethyl-d9)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-2-propanol Benzoate (Ester); (±)-Bopindolol-d9; rac Bopindolol-d9

Database IDs

• PubChem SID: 162256833
• PubChem CID: 71314196

CALCULATED PROPERTIES

• Acid pKa: 16.797941
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.534566
• LogD (pH = 7.4): 2.7915826
• Log P: 4.668419
• Molar Refractivity: 111.0719 cm^3
• Polarizability: 44.592506 Å^3
• Polar Surface Area: 63.35 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B675402

Labelled Bopindolol. Bopindolol is an ester prodrug of Pindolol (P468000). Bopindolol is a long acting β-adrenoceptor blocking agent. Bopindolol displays antispasmogenic activity mediated by α1-adrenoceptors and 5-HT2 receptors.

REFERENCES

• Turner, D.R. et al.: Br. J. Clin. Pharmacol., 17, 295 (1984)
• Brodde, O.E. et al.: J. Cardio. Pharmacol., 8, S70 91986); Doggrell, S.A.: Med, Sci. Res., 17, 681 (1984)