(1S,5S,13R)-14-(2H3)methoxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,14,16-pentaene

• ChemBase ID: 178491
• Molecular Formular: C19H21NO3
• Molecular Mass: 311.37494
• Monoisotopic Mass: 311.15214354
• SMILES: c1(c2c3c(cc1)C[C@H]1C4=CC=C([C@@H]([C@]34CCN1C)O2)OC)OC
• Canonical SMILES: COC1=CC=C2[C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)C)ccc1OC
• InChI: InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13-,18-,19-/m0/s1
• InChIKey: FQXXSQDCDRQNQE-AGRHKRQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R)-14-(^2H₃)methoxy-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),8,10,14,16-pentaene
• IUPAC Traditional name: (1S,5S,13R)-14-(^2H₃)methoxy-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),8,10,14,16-pentaene
• Synonyms: 6,7,8,14-Tetradehydro-4,5α-epoxy-3-methoxy-6-(methoxy-d3)-17-methylmorphinan; Thebaine 6-O-Methyl-d3

Database IDs

• CAS Number: 18161-81-4
• PubChem SID: 164234401
• PubChem CID: 71752500

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.2559863
• LogD (pH = 7.4): 0.5094419
• Log P: 1.5322096
• Molar Refractivity: 90.6597 cm^3
• Polarizability: 34.35827 Å^3
• Polar Surface Area: 30.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T342453

Labelled Thebaine. Controllled substance (opiate).

REFERENCES

• Csokan, Z., et al.: Anal. Chem., 124, 344 (1942)
• Barber, R., et al.: J. Med.Chem., 18, 1074 (1942)
• Bird, D., et al.: Plant Cell, 15, 2626 (1942)
• Park, S., et al.: Plant Mol. Biol., 51, 153 (1942)