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

• ChemBase ID: 175914
• Molecular Formular: C18H19NO3
• Molecular Mass: 297.34836
• Monoisotopic Mass: 297.13649347
• SMILES: c1(c2c3c(cc1)C[C@H]1C4=CC=C([C@@H]([C@]34CCN1C)O2)OC)O
• Canonical SMILES: COC1=CC=C2[C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)C)ccc1O
• InChI: InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,12,17,20H,7-9H2,1-2H3/t12-,17-,18-/m0/s1
• InChIKey: ZKLXUUYLEHCAMF-IGNZVWTISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R)-14-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-pentaen-10-ol
• IUPAC Traditional name: (1S,5S,13R)-14-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-pentaen-10-ol
• Synonyms: (5α)-6,7,8,14-Tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol; 3-O-Demethylthebaine; Oripavine

Database IDs

• CAS Number: 467-04-9
• PubChem SID: 164231824
• PubChem CID: 120687

CALCULATED PROPERTIES

• Acid pKa: 10.070539
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.4085258
• LogD (pH = 7.4): 0.35481924
• Log P: 1.2523338
• Molar Refractivity: 86.1774 cm^3
• Polarizability: 32.445 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: Light Tan Solid
• Melting Point: >155°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - O675000

The major metabolite of Thebaine. Oripavine possesses an analgesic potency comparable to Morphine; it is not clinically useful due to severe toxicity and low therapeutic index. An opiate.

REFERENCES

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