(1S,5S,13R,14S,17R)-10-(2H3)methoxy-4-(2H3)methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol

• ChemBase ID: 164943
• Molecular Formular: C18H21NO3
• Molecular Mass: 299.36424
• Monoisotopic Mass: 299.15214354
• SMILES: [C@H]12[C@H](C=C[C@@H]3[C@]41c1c(C[C@@H]3N(CC4)C)ccc(c1O2)OC)O
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@@H](C2)[C@@H]4C=C[C@@H]1O)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/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12-,13-,17-,18-/m0/s1
• InChIKey: OROGSEYTTFOCAN-DHMYTKHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R,14S,17R)-10-(^2H₃)methoxy-4-(^2H₃)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-ol
• IUPAC Traditional name: (1S,5S,13R,14S,17R)-10-(^2H₃)methoxy-4-(^2H₃)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-ol
• Synonyms: (5α,6α)-7,8-Didehydro-4,5-epoxy-3-methoxy-d3-17-(methyl-d3)-morphinan-6-ol; (-)-Codeine-d6; Codicept-d6; Coducept-d6; Methylmorphine-d6; Morphine-d6 3-Methyl Ether; l-Codeine-d6; Codeine-d6

Database IDs

• CAS Number: 1007844-34-9
• PubChem SID: 162259077
• PubChem CID: 71314974

CALCULATED PROPERTIES

• Acid pKa: 13.78274
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.9427414
• LogD (pH = 7.4): -0.44837403
• Log P: 1.3429513
• Molar Refractivity: 84.6047 cm^3
• Polarizability: 32.611034 Å^3
• Polar Surface Area: 41.93 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 146-148°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C634083

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.Controlled substance (opiate).

REFERENCES

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