(1S,5S,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-yl methanesulfonate

• ChemBase ID: 164944
• Molecular Formular: C19H23NO5S
• Molecular Mass: 377.45462
• Monoisotopic Mass: 377.12969384
• SMILES: [C@H]12[C@H](C=C[C@@H]3[C@]41c1c(C[C@@H]3N(CC4)C)ccc(c1O2)OC)OS(=O)(=O)C
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@@H](C2)[C@@H]4C=C[C@@H]1OS(=O)(=O)C)C
• InChI: InChI=1S/C19H23NO5S/c1-20-9-8-19-12-5-7-15(25-26(3,21)22)18(19)24-17-14(23-2)6-4-11(16(17)19)10-13(12)20/h4-7,12-13,15,18H,8-10H2,1-3H3/t12-,13-,15-,18-,19-/m0/s1
• InChIKey: VZMWUVNHCHKXJT-QBQAKCNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-14-yl methanesulfonate
• IUPAC Traditional name: (1S,5S,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-14-yl methanesulfonate
• Synonyms: (5α,6α)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methyl-morphinan-6-ol 6-Methanesulfonate; Codeine 6-Methanesulfonate

Database IDs

• CAS Number: 22952-80-3
• PubChem SID: 162259078
• PubChem CID: 71314975

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.9952155
• LogD (pH = 7.4): -0.48474368
• Log P: 1.2791156
• Molar Refractivity: 97.3572 cm^3
• Polarizability: 38.81366 Å^3
• Polar Surface Area: 65.07 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White Solid

Safety Information

• Storage Condition: Controlled Substance, Freezer

DETAILS

Toronto Research Chemicals - C634085

Protected Codeine (C634075). Present in opium from 0.7% to 2.5%, depending on the source. Weak narcotic analgesic, perhaps due to conversion to morphine, with minimal hypnotic properties; potent antitussive.

REFERENCES

• Eddy, S., et al.: J. Pharmacol. Exp. Ther., 67, 127 (1939)
• Muhtadi, F.J., et al.: Anal. Profiles Drug Subs., 10, 93 (1981).