2-[(1R,9R,10R)-4-hydroxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-17-yl]-1-phenylethan-1-one

• ChemBase ID: 130434
• Molecular Formular: C24H27NO2
• Molecular Mass: 361.47668
• Monoisotopic Mass: 361.20417911
• SMILES: C1CC[C@@]23CCN([C@@H]([C@@H]2C1)Cc1c3cc(cc1)O)CC(=O)c1ccccc1
• Canonical SMILES: Oc1ccc2c(c1)[C@]13CCCC[C@H]3[C@@H](C2)N(CC1)CC(=O)c1ccccc1
• InChI: InChI=1S/C24H27NO2/c26-19-10-9-18-14-22-20-8-4-5-11-24(20,21(18)15-19)12-13-25(22)16-23(27)17-6-2-1-3-7-17/h1-3,6-7,9-10,15,20,22,26H,4-5,8,11-14,16H2/t20-,22+,24+/m0/s1
• InChIKey: RCYBMSQOSGJZLO-BGWNEDDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,9R,10R)-4-hydroxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-17-yl]-1-phenylethan-1-one
• IUPAC Traditional name: levophenacylmorphan
• Synonyms: 17-(2-Oxo-2-phenylethyl)morphinan-3-ol; 2-(1,3,4,9,10,10a-Hexahydro-6-hydroxy-2H-10,4a-iminoethanophenanthren-11-yl)acetophenone; 17-Phenacylmorphinan-3-ol; (-)-3-Hydroxy-N-phenacylmorphinan; Benzorphanol; Levophenacylmorphinan-3-ol; NIH 7525; Ro 4-0288/1; Levophenacylmorphan; Levophenacylmorphan

Database IDs

• CAS Number: 10061-32-2
• PubChem SID: 162224713
• PubChem CID: 5362482
• Unique Ingredient Identifier: 7Q24AL2BR2
• Wikipedia Title: Levophenacylmorphan

CALCULATED PROPERTIES

• Acid pKa: 10.261663
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.0833335
• LogD (pH = 7.4): 4.4376063
• Log P: 4.5801024
• Molar Refractivity: 107.9826 cm^3
• Polarizability: 41.876854 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Legal Status: Schedule I (US)

DETAILS

Toronto Research Chemicals - L375900

Morphinan derivative useful as antitussive and analgesic. An opiate.

REFERENCES

• Musumarra, G., et al.: J. Chromatogr. Sci., 22, 538 (1984)