(1S,5S,13R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one

• ChemBase ID: 170044
• Molecular Formular: C18H21NO3
• Molecular Mass: 299.36424
• Monoisotopic Mass: 299.15214354
• SMILES: [C@H]12C(=O)CCC3[C@]41c1c(C[C@@H]3N(CC4)C)ccc(c1O2)OC
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@@H](C2)C4CCC1=O)C
• InChI: InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-12,17H,4-5,7-9H2,1-2H3/t11?,12-,17-,18-/m0/s1
• InChIKey: LLPOLZWFYMWNKH-KSWAHXJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R)-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-trien-14-one
• IUPAC Traditional name: (1S,5S,13R)-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-trien-14-one
• Synonyms: (5α)-4,5-Epoxy-3-methoxy-17-methylmorphinan-6-one; (-)-Dihydrocodeinone; 6-Oxo-7,8-dihydrocodeine; Bekadid; Dihydrocodeinone; Hydrocodon; Multacodin; NSC 19044; Hydrocodone

Database IDs

• CAS Number: 125-29-1
• PubChem SID: 164225954
• PubChem CID: 22562

CALCULATED PROPERTIES

• Acid pKa: 18.002748
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.998823
• LogD (pH = 7.4): 0.7307476
• Log P: 1.960304
• Molar Refractivity: 82.7447 cm^3
• Polarizability: 32.383915 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Beige Solid
• Melting Point: 194-197°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H714610

Analgesic (narcotic); antitussive.Controlled substance (opiate).

REFERENCES

• Eddy, N.B., et al.: J. Pharmacol. Exp. Ther., 52, 468 (1934)
• Stein, A., et al.: Pharmazie, 10, 180 (1934)
• Peer, C., et al.: J. Anal. Toxicol., 31, 515 (1934)