(1S,9R,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-8-one

• ChemBase ID: 172060
• Molecular Formular: C18H23NO2
• Molecular Mass: 285.38072
• Monoisotopic Mass: 285.17287898
• SMILES: c1(cc2c(cc1)C(=O)[C@H]1[C@@H]3[C@]2(CCCC3)CCN1C)OC
• Canonical SMILES: COc1ccc2c(c1)[C@@]13CCCC[C@@H]3[C@H](C2=O)N(CC1)C
• InChI: InChI=1S/C18H23NO2/c1-19-10-9-18-8-4-3-5-14(18)16(19)17(20)13-7-6-12(21-2)11-15(13)18/h6-7,11,14,16H,3-5,8-10H2,1-2H3/t14-,16-,18+/m1/s1
• InChIKey: UOCRGKKCNCIQCZ-KYJSFNMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-8-one
• IUPAC Traditional name: (1S,9R,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-8-one
• Synonyms: (9R,13S,14S)-3-Methoxy-17-methylmorphinan-10-one; 10-Oxo Dextromethorphan; (9R,13S,14S)-3-Methoxy-10-oxo-N-methylmorphinan; 10-Keto Dextromethorphan

Database IDs

• CAS Number: 57969-05-8
• PubChem SID: 164227970
• PubChem CID: 21780010

CALCULATED PROPERTIES

• Acid pKa: 17.579145
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.77647734
• LogD (pH = 7.4): 2.451515
• Log P: 2.8650515
• Molar Refractivity: 83.1724 cm^3
• Polarizability: 32.491783 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 184-186°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - K187800

A product formed from the photochemical reaction of Dextromethorphan (D299455) after light or sunlight exposure.

REFERENCES

• Halstead, G.W., et al.: J. Pharm. Sci., 71, 1108 (1982)
• Koeppel, C., et al.: Arzneim.-Forsch., 37, 1304 (1982)