3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol

• ChemBase ID: 166603
• Molecular Formular: C15H23NO2
• Molecular Mass: 249.34862
• Monoisotopic Mass: 249.17287898
• SMILES: C1CCC[C@]([C@@H]1CN(C)C)(c1cc(ccc1)O)O
• Canonical SMILES: CN(C[C@@H]1CCCC[C@@]1(O)c1cccc(c1)O)C
• InChI: InChI=1S/C15H23NO2/c1-16(2)11-13-6-3-4-9-15(13,18)12-7-5-8-14(17)10-12/h5,7-8,10,13,17-18H,3-4,6,9,11H2,1-2H3/t13-,15+/m0/s1
• InChIKey: UWJUQVWARXYRCG-DZGCQCFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol
• IUPAC Traditional name: 3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol
• Synonyms: 3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol; (-)-2-[(Dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol; ODT; (-)-O-Demethyltramadol; (-)-O-Desmethyl Tramadol

Database IDs

• CAS Number: 144830-15-9
• PubChem SID: 162260736
• PubChem CID: 15645279

CALCULATED PROPERTIES

• Acid pKa: 9.616299
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.99180937
• LogD (pH = 7.4): 0.48243254
• Log P: 1.7186112
• Molar Refractivity: 73.7869 cm^3
• Polarizability: 28.921167 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethanol; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 131-142°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D294745

A optically active metabolite of Tramadol.

REFERENCES

• Lintz, V.W., et al.: Arzneim.-Forsch./Drug Res., 31, II, 11, 1932 (1981)