(1s,4s)-4-{[(2-amino-3,5-dibromophenyl)methyl]amino}(1,2,2,6,6-2H5)cyclohexan-1-ol

• ChemBase ID: 159770
• Molecular Formular: C13H18Br2N2O
• Molecular Mass: 378.10282
• Monoisotopic Mass: 375.97858721
• SMILES: c1c(cc(c(c1CN[C@H]1CC[C@H](CC1)O)N)Br)Br
• Canonical SMILES: O[C@@H]1CC[C@@H](CC1)NCc1cc(Br)cc(c1N)Br
• InChI: InChI=1S/C13H18Br2N2O/c14-9-5-8(13(16)12(15)6-9)7-17-10-1-3-11(18)4-2-10/h5-6,10-11,17-18H,1-4,7,16H2/t10-,11+
• InChIKey: JBDGDEWWOUBZPM-PHIMTYICSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1s,4s)-4-{[(2-amino-3,5-dibromophenyl)methyl]amino}(1,2,2,6,6-^2H₅)cyclohexan-1-ol
• IUPAC Traditional name: (1s,4s)-4-{[(2-amino-3,5-dibromophenyl)methyl]amino}(1,2,2,6,6-^2H₅)cyclohexan-1-ol
• Synonyms: cis-4-[[(2-Amino-3,5-dibromophenyl)methyl]amino]cyclohexanol-d5; Ambroxol EP Impurity D-d5; rac-cis-Ambroxol-d5

Database IDs

• PubChem SID: 162253905
• PubChem CID: 45038101

CALCULATED PROPERTIES

• Acid pKa: 15.256605
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.48352024
• LogD (pH = 7.4): 0.76556224
• Log P: 2.652726
• Molar Refractivity: 81.9357 cm^3
• Polarizability: 31.45754 Å^3
• Polar Surface Area: 58.28 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A575907

Labelled anaologue of cis-Ambroxol, the cis-isomeric impurity of Ambroxol (A575905). cis-Ambroxol is a metabolite Bromhexine (B678600).

REFERENCES

• Liu, J. et al.: J. Pharmac. Biomed. Anal., 51, 1134 (2010)
• Schmid, J.: J. Chrom. Biomed. Appl., 414, 65 (2010)