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

• ChemBase ID: 170191
• Molecular Formular: C18H25NO2
• Molecular Mass: 287.3966
• Monoisotopic Mass: 287.18852905
• SMILES: c1(cc2c(cc1)[C@H]([C@H]1[C@H]3[C@]2(CCCC3)CCN1C)O)OC
• Canonical SMILES: COc1ccc2c(c1)[C@@]13CCCC[C@H]3[C@H]([C@@H]2O)N(CC1)C
• InChI: InChI=1S/C18H25NO2/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/h6-7,11,14,16-17,20H,3-5,8-10H2,1-2H3/t14-,16+,17+,18-/m0/s1
• InChIKey: VHADEHXKPTVSKZ-HPBDAGMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,8R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-8-ol
• IUPAC Traditional name: (1S,8R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-8-ol
• Synonyms: (9S,13S,14S)-3-Methoxy-10β-hydroxy-N-methylmorphinan; (9α,13α,14α)-3-Methoxy-10β-hydroxy-N-methylmorphinan; 10β-Hydroxy Dextromethorphan Hydrochloride

Database IDs

• PubChem SID: 164226101
• PubChem CID: 13309234

CALCULATED PROPERTIES

• Acid pKa: 13.852836
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.76098907
• LogD (pH = 7.4): 0.64696085
• Log P: 2.5747783
• Molar Refractivity: 83.7707 cm^3
• Polarizability: 32.979218 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H825235

A major 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)