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

• ChemBase ID: 166731
• Molecular Formular: C18H26ClNO2
• Molecular Mass: 323.85754
• Monoisotopic Mass: 323.16520676
• SMILES: c1(cc2c(cc1)C[C@H]1[C@@H]3[C@]2(CCCC3)CC[N@+]1([O-])C)OC.Cl
• Canonical SMILES: COc1ccc2c(c1)[C@@]13CCCC[C@@H]3[C@H](C2)[N@@+](CC1)([O-])C.Cl
• InChI: InChI=1S/C18H25NO2.ClH/c1-19(20)10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(21-2)12-16(13)18;/h6-7,12,15,17H,3-5,8-11H2,1-2H3;1H/t15-,17+,18+,19-;/m1./s1
• InChIKey: JJXFRVFGFPYDCZ-SNNOFRMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9S,10S,17R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-17-ium-17-olate hydrochloride
• IUPAC Traditional name: (1S,9S,10S,17R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-17-ium-17-olate hydrochloride
• Synonyms: (9α,13α,14α)-3-Methoxy-17-methylmorphinan 17-Oxide; (9S,13S,14S)-3-Methoxy-17-methylmorphinan 17-Oxide; (+)-Dextromethorphan N-Oxide; Dextromethorphan N-Oxide

Database IDs

• CAS Number: 1177494-18-6
• PubChem SID: 162260864
• PubChem CID: 71315858

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.369212
• LogD (pH = 7.4): 2.3693967
• Log P: 2.369399
• Molar Refractivity: 84.6081 cm^3
• Polarizability: 32.567467 Å^3
• Polar Surface Area: 36.11 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 166-168°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D299465

The N-Oxide Dextromethorphan (D299455) used in the process for preparation of (+)-Morphinan N-oxides.

REFERENCES

• Abdel-Monem, M., et al.: J. Med. Chem., 15, 208 (1972)
• Berenyi, S., et al.: Curr. Med. Chem., 16, 3215 (1972)
• Emond, P., et al.: Bioorg. Med. Chem., 9, 1849 (1972)