(1S,5S,13S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-10-ol

• ChemBase ID: 166640
• Molecular Formular: C17H21NO2
• Molecular Mass: 271.35414
• Monoisotopic Mass: 271.15722892
• SMILES: c1(c2c3c(cc1)C[C@H]1[C@H]4[C@@]3([C@H](CCC4)O2)CCN1C)O
• Canonical SMILES: CN1CC[C@@]23[C@@H]4[C@@H]1Cc1c3c(O[C@H]2CCC4)c(cc1)O
• InChI: InChI=1S/C17H21NO2/c1-18-8-7-17-11-3-2-4-14(17)20-16-13(19)6-5-10(15(16)17)9-12(11)18/h5-6,11-12,14,19H,2-4,7-9H2,1H3/t11-,12-,14-,17+/m0/s1
• InChIKey: LNNWVNGFPYWNQE-MYLCLEHYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13S,17R)-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-trien-10-ol
• IUPAC Traditional name: (1S,5S,13S,17R)-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-trien-10-ol
• Synonyms: (5α)-4,5-Epoxy-17-methylmorphinan-3-ol; 6-Deoxy-7,8-dihydromorphine; 4,5-Epoxy-3-hydroxy-N-methylmorphinan; Deoxydihydromorphine D; Desomorphine; Dihydrodeoxymorphine; Dihydrodesoxymorphine D; Dihydroepoxymorphine; Permonid; Desomorphine

Database IDs

• CAS Number: 427-00-9
• PubChem SID: 162260773
• PubChem CID: 61114

CALCULATED PROPERTIES

• Acid pKa: 10.350201
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.90902036
• LogD (pH = 7.4): 0.36914033
• Log P: 2.1093748
• Molar Refractivity: 77.7983 cm^3
• Polarizability: 30.317175 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Off-White to Light Beige Solid
• Melting Point: 188-190°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D296900

Analgesic (narcotic). Controlled substance (opium derivative).

REFERENCES

• Zhao, M., et al.: Bioorg. Med. Chem., 15, 2815 (2007)
• Zhao, M., et al.: Eur. J. Med. Chem., 43, 1048 (2007)
• Roy, K., et al.: Eur. J. Med. Chem., 44, 2913 (2007)