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

• ChemBase ID: 175718
• Molecular Formular: C18H19NO3
• Molecular Mass: 297.34836
• Monoisotopic Mass: 297.13649347
• SMILES: c1(c2c3c(cc1)C[C@@H]1C4=CC=C([C@@H]([C@]34CCN1)O2)OC)OC
• Canonical SMILES: COC1=CC=C2[C@@]34[C@H]1Oc1c4c(C[C@H]2NCC3)ccc1OC
• InChI: InChI=1S/C18H19NO3/c1-20-13-5-3-10-9-12-11-4-6-14(21-2)17-18(11,7-8-19-12)15(10)16(13)22-17/h3-6,12,17,19H,7-9H2,1-2H3/t12-,17+,18+/m1/s1
• InChIKey: QKQQEIVDLRUZRP-UUWFMWQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R)-10,14-dimethoxy-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,5R,13R)-10,14-dimethoxy-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: (5α)-6,7,8,14-Tetradehydro-4,5-epoxy-3,6-dimethoxymorphinan; Northebaine; (-)-Northebaine; N-Demethylthebaine; N-Northebaine; 17-Northebaine

Database IDs

• CAS Number: 2579-67-1
• PubChem SID: 164231628
• PubChem CID: 10881027

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.9922557
• LogD (pH = 7.4): -0.7610975
• Log P: 1.1491617
• Molar Refractivity: 85.365 cm^3
• Polarizability: 32.516727 Å^3
• Polar Surface Area: 39.72 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N826500

A metabolite of Thebaine.Controlled substance.

REFERENCES

• Barber, R., et al.: J. Med. Chem., 18, 1074 (1975)
• Yamazoe, Y., et al.: J. Pharmacol., 31, 433 (1975)