4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]naphthalen-1-ol hydrochloride

• ChemBase ID: 171203
• Molecular Formular: C16H22ClNO3
• Molecular Mass: 311.80378
• Monoisotopic Mass: 311.12882125
• SMILES: c1cccc2c1c(ccc2O)OC[C@H](CNC(C)C)O.Cl
• Canonical SMILES: O[C@H](COc1ccc(c2c1cccc2)O)CNC(C)C.Cl
• InChI: InChI=1S/C16H21NO3.ClH/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16;/h3-8,11-12,17-19H,9-10H2,1-2H3;1H/t12-;/m0./s1
• InChIKey: ROUJENUXWIFONU-YDALLXLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]naphthalen-1-ol hydrochloride
• IUPAC Traditional name: 4-[(2S)-2-hydroxy-3-(isopropylamino)propoxy]naphthalen-1-ol hydrochloride
• Synonyms: 4-[(2S)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol Hydrochloride; (-)-4-Hydroxypropranolol Hydrochloride; (-)-Hydroxypropranolol Hydrochloride; (S)-4-Hydroxy Propranolol HydrochlorideDiscontinued See H952533

Database IDs

• CAS Number: 135201-50-2
• PubChem SID: 164227113
• PubChem CID: 46781877

CALCULATED PROPERTIES

• Acid pKa: 9.301043
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.90915066
• LogD (pH = 7.4): 0.084633276
• Log P: 1.5727339
• Molar Refractivity: 78.8066 cm^3
• Polarizability: 32.33075 Å^3
• Polar Surface Area: 61.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 156-158°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - H952531

(S)-4-Hydroxy Propranolol is the main metabolite of (S)-Propranolol (P831795).

REFERENCES

• Shwed, J., et al.: Xenobiotica, 22, 973 (1992)
• Fujita, K., et al.: Biol. Pharm. Bull., 22, 446 (1992)
• Walle, U., et al.: Drug Metab. Dispos., 30, 564 (1992)