(1r,4r)-4-(6,8-dibromo-1,2,3,4-tetrahydroquinazolin-3-yl)cyclohexan-1-ol

• ChemBase ID: 159771
• Molecular Formular: C14H18Br2N2O
• Molecular Mass: 390.11352
• Monoisotopic Mass: 387.97858721
• SMILES: c1c(cc(c2c1CN([C@@H]1CC[C@H](CC1)O)CN2)Br)Br
• Canonical SMILES: O[C@@H]1CC[C@H](CC1)N1CNc2c(C1)cc(cc2Br)Br
• InChI: InChI=1S/C14H18Br2N2O/c15-10-5-9-7-18(8-17-14(9)13(16)6-10)11-1-3-12(19)4-2-11/h5-6,11-12,17,19H,1-4,7-8H2/t11-,12-
• InChIKey: AJOQVCHLLULVGK-HAQNSBGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1r,4r)-4-(6,8-dibromo-1,2,3,4-tetrahydroquinazolin-3-yl)cyclohexan-1-ol
• IUPAC Traditional name: (1r,4r)-4-(6,8-dibromo-2,4-dihydro-1H-quinazolin-3-yl)cyclohexan-1-ol
• Synonyms: trans-4-(6,8-Dibromo-1,4-dihydro-3(2H)-quinazolinyl)cyclohexanol Hydrochloride; NA 873 Hydrochloride; Ambroxol EP Impurity B Hydrochloride; Ambroxol Cyclic Impurity Hydrochloride

Database IDs

• PubChem SID: 162253906
• PubChem CID: 52914942

CALCULATED PROPERTIES

• Acid pKa: 14.8315325
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.2601094
• LogD (pH = 7.4): 3.2758496
• Log P: 3.276054
• Molar Refractivity: 85.5643 cm^3
• Polarizability: 32.56954 Å^3
• Polar Surface Area: 35.5 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A575910

Ambroxol Cyclic Impurity is a metabolite as well as an impurity of the bronchosecretolytic drug, Ambroxol (A575900).

REFERENCES

• Hammer, R. et al.: Arzneim.-Forsch., 28, 899 (1978)
• Nieder, M. et al.: HRC & CC, 9, 561 (1978)
• Huq, F. et al.: J. Pharmacol. Toxicol., 3, 147 (1978)