9-{10,14-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-9-yl}-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraene-10,14-diol

• ChemBase ID: 129163
• Molecular Formular: C34H36N2O6
• Molecular Mass: 568.65944
• Monoisotopic Mass: 568.25733688
• SMILES: CN1CCC23C4C1Cc1c2c(c(c(c1)c1cc2c5c(c1O)OC1C65CCN(C(C2)C6C=CC1O)C)O)OC3C(C=C4)O
• Canonical SMILES: CN1CCC23C4C1Cc1c3c(OC2C(C=C4)O)c(c(c1)c1cc2CC3N(C)CCC45c2c(c1O)OC4C(O)C=CC35)O
• InChI: InChI=1S/C34H36N2O6/c1-35-9-7-33-19-3-5-23(37)31(33)41-29-25(33)15(13-21(19)35)11-17(27(29)39)18-12-16-14-22-20-4-6-24(38)32-34(20,8-10-36(22)2)26(16)30(42-32)28(18)40/h3-6,11-12,19-24,31-32,37-40H,7-10,13-14H2,1-2H3
• InChIKey: FOJYFDFNGPRXDR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-{10,14-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-9-yl}-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraene-10,14-diol
• IUPAC Traditional name: pseudomorphine
• Synonyms: Pseudomorphine; (5α,6α)-(5'α,6'α-7,7',8,8'-Tetradehydro-4,5:4',5'-diepoxy-17,17'-dimethyl-[2,2'-bimorphinan]-3,3',6,6'-tetrol; 2,2'-Dehydrodimorphine; Dehydromorphine; Oxydimorphine; Morphine Impurity; Pseudo Morphine (Morphine Impurity)

Database IDs

• CAS Number: 125-24-6
• PubChem SID: 162223460
• PubChem CID: 234570
• Chemspider ID: 4590027
• Unique Ingredient Identifier: AEZ78QX2G7
• Wikipedia Title: Pseudomorphine

CALCULATED PROPERTIES

• Acid pKa: 9.328563
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.599711
• LogD (pH = 7.4): -1.773907
• Log P: 1.039397
• Molar Refractivity: 159.323 cm^3
• Polarizability: 62.01327 Å^3
• Polar Surface Area: 105.86 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Beige Solid
• Melting Point: >225°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - P839540

A degradation product of Morphine. A dimolecular base formed by the gentle oxidation of Morphine in alkaline solution. Name Pseudomorphine is also used for the C17 alkaloid base.

REFERENCES

• Rosenberger, R., et al.: J. Gen. Microbiol., 22, 726 (1960)
• Rahim, M., et al.: J. Biol. Chem., 241, 3615 (1960)
• Dolezalova, M., et al.: J. Pharm. Biomed. Anal., 10, 507 (1960)
• Willey, D., et al.: Biochem. J., 290, 539 (1960)