1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one hydrochloride

• ChemBase ID: 133155
• Molecular Formular: C21H28ClNO3
• Molecular Mass: 377.90492
• Monoisotopic Mass: 377.17577144
• SMILES: CCCNCC(COc1ccccc1C(=O)CCc1ccccc1)O.Cl
• Canonical SMILES: CCCNCC(COc1ccccc1C(=O)CCc1ccccc1)O.Cl
• InChI: InChI=1S/C21H27NO3.ClH/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17;/h3-11,18,22-23H,2,12-16H2,1H3;1H
• InChIKey: XWIHRGFIPXWGEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one hydrochloride
• IUPAC Traditional name: propafenone hydrochloride
• Synonyms: 1-[2-(2-Hydroxy-3-(propylamino)propoxy)phenyl]-3-phenyl-1-propanone hydrochloride; Propafenone hydrochloride; 1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one hydrochloride; 1-[2-[2-Hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone Hydrochloride; 2'-[2-Hydroxy-3-(propylamino)propoxy]-3-phenylpropiophenone Hydrochloride; Arythmol; Pronon; Rythmol; Rytmonorm; Propafenone Hydrochloride

Database IDs

• CAS Number: 34183-22-7
• EC Number: 251-867-9
• MDL Number: MFCD00079243
• PubChem SID: 162227432; 24278636
• PubChem CID: 36708

CALCULATED PROPERTIES

• Acid pKa: 14.085882
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.34713113
• LogD (pH = 7.4): 1.3413471
• Log P: 3.5367227
• Molar Refractivity: 100.2064 cm^3
• Polarizability: 39.38228 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 149-151°C; 174 - 176°C
• Hydrophobicity(logP): 3.636

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 46-22
• Safety Statements: 53-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H340
• GHS Precautionary statements: P201-P308 + P313
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ABCB1(5243), ADRB1(153), ADRB2(154), ADRB3(155), CYP1A2(1544)

Product Information

• Purity: 95%

DETAILS

Sigma Aldrich - P4670

Biochem/physiol Actions
Blocks hKv1.5 and ATP-sensitive K+ channels; class 1C antiarrhythmic agent that is also an antagonist at β adrenergic receptors.

Toronto Research Chemicals - P757500

Sodium channel blocker. Antiarrhythmic (class IC).

REFERENCES

• Hollmann, M., et al.: Arzneim.-Forsch., 33, 763 (1983)
• Bryson, H. M., et al.:Drugs, 45, 85 (1983)
• Rae, A. P., et al.: Am. J. Cardiol., 82, 59N (1983)