(3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-ol

• ChemBase ID: 172704
• Molecular Formular: C21H29NO
• Molecular Mass: 311.46106
• Monoisotopic Mass: 311.22491455
• SMILES: [C@H](C(C[C@H](C)N(C)C)(c1ccccc1)c1ccccc1)(O)CC
• Canonical SMILES: CC[C@@H](C(c1ccccc1)(c1ccccc1)C[C@@H](N(C)C)C)O
• InChI: InChI=1S/C21H29NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17,20,23H,5,16H2,1-4H3/t17-,20-/m0/s1
• InChIKey: QIRAYNIFEOXSPW-PXNSSMCTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-ol
• IUPAC Traditional name: (3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-ol
• Synonyms: (αS)-β-[(2S)-2-(dimethylamino)propyl]-α-ethyl-β-phenylbenzeneethanol; (S,S)-(-)-6-(Dimethylamino)-4,4-diphenyl-3-heptanol; [S-(R*,R*)]-β-[2-(dimethylamino)propyl]-α-ethyl-β-phenylbenzeneethanol; (3S,6S)-Methadol; L-α-Methadol; α-l-Methadol; (-)-α-Methadol

Database IDs

• CAS Number: 14019-10-4
• PubChem SID: 164228614
• PubChem CID: 3041256

CALCULATED PROPERTIES

• Acid pKa: 14.523448
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0457338
• LogD (pH = 7.4): 2.289213
• Log P: 4.443644
• Molar Refractivity: 108.7061 cm^3
• Polarizability: 38.64026 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225861

The enatiomer of (+)-α-Methadol (M225860) and is more effective in binding to opiate receptors. The relative activities of (-)-α-Methadol and (+)-α-Methadol are reversed upon acetylation. A metabolite of (-)-α-Acetylmethadol (A186325).

REFERENCES

• Horng, J.S. et al.: Res. Comm. Chem. Pathol. Pharmacol., 14, 621 (1976)
• Casy, A.F. et al.: J. Med. Chem., 11, 601 (1976)
• Ruemmler, R., et al.: Arzneim.-Forsch., 20, 281 (1976)