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

• ChemBase ID: 166604
• Molecular Formular: C15H24ClNO2
• Molecular Mass: 285.80956
• Monoisotopic Mass: 285.14955669
• SMILES: C1CCC[C@]([C@@H]1CN(C)C)(c1cc(ccc1)O)O.Cl
• Canonical SMILES: CN(C[C@@H]1CCCC[C@@]1(O)c1cccc(c1)O)C.Cl
• InChI: InChI=1S/C15H23NO2.ClH/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;1H/t13-,15+;/m0./s1
• InChIKey: IRGWVAWLHXDKIX-NQQJLSKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol hydrochloride
• IUPAC Traditional name: 3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol hydrochloride
• Synonyms: 3-[(1S,2S)-2-[(Dimethylamino)methyl]-1-hydroxycyclohexyl]phenol Hydrochloride; (1S-cis)-3-[2-[(Dimethylamino)methyl]-1-hydroxycyclohexyl]phenol Hydrochloride; EM 724; (-)-O-Desmethyl Tramadol Hydrochloride

Database IDs

• CAS Number: 148218-19-3
• PubChem SID: 162260737
• PubChem CID: 46781196

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: Ethanol; Methanol; Water
• Apperance: White Solid
• Melting Point: 256-257°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D294750

An optically active metabolite of Tramadol. Enantiomer S.

REFERENCES

• Raffa, R., et al.: J. Pharm. Exp. Ther., 267, 331 (1993)
• Dayer, P., et al.: Drugs, 47, 3 (1993)
• Lai, J., et al.: Eur. J. Pharmacol., 316, 369 (1993)
• Poulsen, L., et al.: Clin. Pharmacol. Ther., 60, 637 (1993)