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

• ChemBase ID: 170192
• Molecular Formular: C18H26ClNO2
• Molecular Mass: 323.85754
• Monoisotopic Mass: 323.16520676
• SMILES: c1(cc2c(cc1)[C@@H]([C@H]1[C@@H]3[C@]2(CCCC3)CCN1C)O)OC.Cl
• Canonical SMILES: COc1ccc2c(c1)[C@@]13CCCC[C@@H]3[C@H]([C@H]2O)N(CC1)C.Cl
• InChI: InChI=1S/C18H25NO2.ClH/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;1H/t14-,16-,17+,18+;/m1./s1
• InChIKey: UFGACSXJDNIRCR-FMMMQXAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,8S,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-ol hydrochloride
• IUPAC Traditional name: (1S,8S,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-ol hydrochloride
• Synonyms: (9S,13S,14S)-3-Methoxy-10α-hydroxy-N-methylmorphinan; (9α,10α,13α,14α)-3-Methoxy-17-methylmorphinan-10-ol; 10α-Hydroxy Dextromethorphan Hydrochloride

Database IDs

• PubChem SID: 164226102
• PubChem CID: 71748850

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

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 170-173°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H825236

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)