5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalen-1-one hydrochloride

• ChemBase ID: 172277
• Molecular Formular: C17H26ClNO3
• Molecular Mass: 327.84624
• Monoisotopic Mass: 327.16012138
• SMILES: C1CC(=O)c2c(C1)c(ccc2)OC[C@H](CNC(C)(C)C)O.Cl
• Canonical SMILES: O[C@H](COc1cccc2c1CCCC2=O)CNC(C)(C)C.Cl
• InChI: InChI=1S/C17H25NO3.ClH/c1-17(2,3)18-10-12(19)11-21-16-9-5-6-13-14(16)7-4-8-15(13)20;/h5-6,9,12,18-19H,4,7-8,10-11H2,1-3H3;1H/t12-;/m0./s1
• InChIKey: DNTDOBSIBZKFCP-YDALLXLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalen-1-one hydrochloride
• IUPAC Traditional name: akβ hydrochloride
• Synonyms: 5-[(2S)-3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-1(2H)-naphthalenone; (S)-5-[3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-1(2H)-naphthalenone; (-)-Bunolol; W 6421A; l-Bunolol; Levobunolol Hydrochloride

Database IDs

• CAS Number: 47141-42-4
• PubChem SID: 164228187
• PubChem CID: 5284409

CALCULATED PROPERTIES

• Acid pKa: 14.085866
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.009857
• LogD (pH = 7.4): -0.036677748
• Log P: 2.1826746
• Molar Refractivity: 83.2824 cm^3
• Polarizability: 32.726128 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Hot Ethanol; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 209-211°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L335000

A non-selective β-adrenoceptor antagonist used as an anticonvulsant.

REFERENCES

• Kaplan, H.R., et al.: Eur. J. Pharm., 16, 237 (1971)
• DiCarlo,F.J., et al.: Clin. Pharm. Ther., 22, 858 (1977)