3-[(1R,2R)-2-(aminomethyl)-1-hydroxycyclohexyl]phenol

• ChemBase ID: 166399
• Molecular Formular: C13H19NO2
• Molecular Mass: 221.29546
• Monoisotopic Mass: 221.14157885
• SMILES: C1CCC[C@@]([C@H]1CN)(c1cc(ccc1)O)O
• Canonical SMILES: NC[C@H]1CCCC[C@]1(O)c1cccc(c1)O
• InChI: InChI=1S/C13H19NO2/c14-9-11-4-1-2-7-13(11,16)10-5-3-6-12(15)8-10/h3,5-6,8,11,15-16H,1-2,4,7,9,14H2/t11-,13+/m1/s1
• InChIKey: MJTYLDGVLFSXDG-YPMHNXCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1R,2R)-2-(aminomethyl)-1-hydroxycyclohexyl]phenol
• IUPAC Traditional name: 3-[(1R,2R)-2-(aminomethyl)-1-hydroxycyclohexyl]phenol
• Synonyms: (+)-O-Desmethyl-N,N-bisdesmethyl Tramadol

Database IDs

• CAS Number: 1235568-21-4
• PubChem SID: 162260532
• PubChem CID: 10220107

CALCULATED PROPERTIES

• Acid pKa: 9.1840315
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.5079147
• LogD (pH = 7.4): -0.64581835
• Log P: 0.6846154
• Molar Refractivity: 63.7176 cm^3
• Polarizability: 25.233875 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 83-85°C

DETAILS

Toronto Research Chemicals - D291155

A optically active metabolite of Tramadol.

REFERENCES

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