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

• ChemBase ID: 166601
• 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+;/m1./s1
• InChIKey: IRGWVAWLHXDKIX-PBCQUBLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol hydrochloride
• IUPAC Traditional name: 3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol hydrochloride
• Synonyms: 3-[(rel-1R,2R)2-[(Dimethylamino)methyl]-1-hydroxycyclohexyl]phenol Hydrochloride; 2-[(rel-1R, 2R)(Dimethylamino)methyl]-1-(m-hydroxyphenyl)cyclohexanol Hydrochloride; O-Desmethyl Tramadol Hydrochloride; 3-[(1R,2R)-2-[(Dimethylamino)methyl]-1-hydroxycyclohexyl]phenol Hydrochloride; (1R-cis)-3-[2-[(Dimethylamino)methyl]-1-hydroxycyclohexyl]phenol Hydrochloride; EM 723; (+)-O-Desmethyl Tramadol Hydrochloride

Database IDs

• CAS Number: 185453-02-5; 148262-77-5
• PubChem SID: 162260734
• PubChem CID: 9838802

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: Methanol; Water
• Apperance: White Solid
• Melting Point: 219-221°C; 248-250°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D294755

An optically active metabolite of Tramadol. Enantiomer R.

Toronto Research Chemicals - D294740

A metabolite of Tramadol, an analgesic.

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)
• Frink, M.C., et al.: Arzneim-Forsch., 46, 1029 (1996)