[(2S)-2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine

• ChemBase ID: 153378
• Molecular Formular: C14H20N2O2
• Molecular Mass: 248.3208
• Monoisotopic Mass: 248.15247789
• SMILES: CC(C)NC[C@@H](COc1cccc2c1cc[nH]2)O
• Canonical SMILES: O[C@H](COc1cccc2c1cc[nH]2)CNC(C)C
• InChI: InChI=1S/C14H20N2O2/c1-10(2)16-8-11(17)9-18-14-5-3-4-13-12(14)6-7-15-13/h3-7,10-11,15-17H,8-9H2,1-2H3/t11-/m0/s1
• InChIKey: JZQKKSLKJUAGIC-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine
• IUPAC Traditional name: (-)-pindolol
• Synonyms: S(-)-Pindolol

Database IDs

• CAS Number: 26328-11-0
• MDL Number: MFCD00153863
• PubChem SID: 162247517; 24278026
• PubChem CID: 688095

CALCULATED PROPERTIES

• Acid pKa: 14.086726
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.5002506
• LogD (pH = 7.4): -0.5322574
• Log P: 1.6929811
• Molar Refractivity: 71.462 cm^3
• Polarizability: 29.42685 Å^3
• Polar Surface Area: 57.28 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble20 mg/mL; 0.1 M NaOH: soluble0.2 mg/mL; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble3.4 mg/mL; H2O: insoluble; methanol: soluble18 mg/mL
• Apperance: white solid
• Optical Rotation: [α]23/D -4.38°, c = 1% in methanol(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADRB1(153), HTR1A(3350), HTR1B(3351)

Product Information

• Empirical Formula (Hill Notation): C14H20N2O2

DETAILS

Sigma Aldrich - P152

Biochem/physiol Actions
β1-adrenoceptor antagonist; putative 5-HT1A serotonin receptor agonist; vasodilator. Active enantiomer of pindolol.