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

• ChemBase ID: 163833
• Molecular Formular: C16H25ClN2O3
• Molecular Mass: 328.8343
• Monoisotopic Mass: 328.15537035
• SMILES: c1cc(c2c(c1)NC(=O)CC2)OCC(CNC(C)(C)C)O.Cl
• Canonical SMILES: OC(COc1cccc2c1CCC(=O)N2)CNC(C)(C)C.Cl
• InChI: InChI=1S/C16H24N2O3.ClH/c1-16(2,3)17-9-11(19)10-21-14-6-4-5-13-12(14)7-8-15(20)18-13;/h4-6,11,17,19H,7-10H2,1-3H3,(H,18,20);1H
• InChIKey: FYBXRCFPOTXTJF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinolin-2-one hydrochloride
• IUPAC Traditional name: carteolol hydrochloride
• Synonyms: 5-[3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-2(1H)-quinolinone Hydrochloride; (+/-)-Carteolol Hydrochloride; dl-Carteolol Hydrochloride; Abbott 43326; OPC-1085; Arteoptic; Endak; Mikelan; Teoptic; Carteolol Hydrochloride

Database IDs

• CAS Number: 51781-21-6
• PubChem SID: 162257968
• PubChem CID: 40127

CALCULATED PROPERTIES

• Acid pKa: 13.408522
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.7840903
• LogD (pH = 7.4): -0.8902049
• Log P: 1.4181689
• Molar Refractivity: 83.1416 cm^3
• Polarizability: 32.03236 Å^3
• Polar Surface Area: 70.59 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 269-272°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C184450

β-Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic; antiglaucoma.

REFERENCES

• Nakagawa, K., et al.: J. Med. Chem., 17, 529 (1974)
• Morita, S., et al.: Biochem. Pharmacol., 25, 1836 (1974)
• Chu, S.Y., et al.: J. Pharm. Sci., 67, 1623 (1974)
• Chiba, S., et al.: Arzneim.-Forsch., 29, 895 (1974)
• Chrisp, P., et al.: Drugs Aging, 2, 58