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

• ChemBase ID: 172703
• 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-FXAWDEMLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-ol
• IUPAC Traditional name: (3R,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-ol
• Synonyms: (αR)-β-[(2R)-2-(Dimethylamino)propyl]-α-ethyl-β-phenylbenzeneethanol; (3R,6R)-(+)-6-(Dimethylamino)-4,4-diphenyl-3-Heptanol; Alphamethadol; D-α-Methadol; (+)-α-Methadol; (R*,R*)-(±)-β-[2-(dimethylamino)propyl]-α-ethyl-β-phenylbenzeneethanol; (±)-α-Methadol; rac α-Methadol

Database IDs

• CAS Number: 17199-54-1; 63869-11-4
• PubChem SID: 164228613
• PubChem CID: 11220657

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 - M225860

A reduction product of (R)-Methadone. Analgesic. The enatiomer of (-)-α-Methadol (M225861) and is less effective in binding to opiate receptors. The relative activities of (-)-α-Methadol and (+)-α-Methadol are reversed upon acetylation.

Toronto Research Chemicals - M225920

A reduction product of Methadone. α-Methadol is an analgesic that effectively binds to opiate receptors.

REFERENCES

• Portoghese, P.S., et al.: J. Med. Chem., 12, 839 (1969)
• Ruemmler, R., et al.: Arzneim.-Forsch., 20, 281 (1969)
• Horng, J.S. et al.: Res. Comm. Chem. Pathol. Pharmacol., 14, 621 (1969)
• Casy, A.F. et al.: J. Med. Chem., 11, 601 (1969)