(1S,5R,13R,14S,17R)-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: 175691
• Molecular Formular: C16H17NO3
• Molecular Mass: 271.31108
• Monoisotopic Mass: 271.12084341
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@H]4[C@@]3([C@H]([C@H](C=C4)O)O2)CCN1)O
• Canonical SMILES: O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2NCC3)ccc1O
• InChI: InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1
• InChIKey: ONBWJWYUHXVEJS-ZTYRTETDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-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: N-normorphine
• Synonyms: (5α,6α)-7,8-Didehydro-4,5-epoxy-morphinan-3,6-diol; (-)-Normorphine; 4,5-Epoxy-3,6-dihydromorphin-7-ene; Demethylmorphine; Desmethylmorphine; N-Demethylmorphine; N-Normorphine; NSC 270042; Normorphine

Database IDs

• CAS Number: 466-97-7
• PubChem SID: 164231601
• PubChem CID: 5462508

CALCULATED PROPERTIES

• Acid pKa: 10.472726
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.4067447
• LogD (pH = 7.4): -1.7316455
• Log P: 0.26351154
• Molar Refractivity: 74.8277 cm^3
• Polarizability: 28.86012 Å^3
• Polar Surface Area: 61.72 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ether; Methanol
• Apperance: Off-White Solid
• Melting Point: >210°C(dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - N740300

Normorphine is a metabolite of Morphine (M652290). This is a controlled substance (opium derivative). Analgesic (narcotic).

REFERENCES

• Coffman, B., et al.: Drug Metab. Dispos., 25, 1 (1997)
• Hanks, G., et al.: Br. J. Cancer, 84, 587 (1997)
• Projean, D., et al.: Xenobiotica, 33, 841 (1997)
• Dale, O., et al.: Br. J. Clin. Pharmacol., 58, 156 (1997)