(1S,5S,13R,14S,17R)-10-(2H3)methoxy-4-(2H3)methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-ol; phosphoperoxol

• ChemBase ID: 167558
• Molecular Formular: C18H24NO7P
• Molecular Mass: 397.359421
• Monoisotopic Mass: 397.12903874
• SMILES: [C@H]12[C@H](CC[C@@H]3[C@]41c1c(C[C@@H]3N(CC4)C)ccc(c1O2)OC)O.P(=O)(=O)OO
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@@H](C2)[C@@H]4CC[C@@H]1O)C.OOP(=O)=O
• InChI: InChI=1S/C18H23NO3.HO4P/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;1-4-5(2)3/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3;1H/t11-,12-,13-,17-,18-;/m0./s1
• InChIKey: MNKIUBAFIYEDKZ-SOJVDZGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R,14S,17R)-10-(^2H₃)methoxy-4-(^2H₃)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-14-ol; phosphoperoxol
• IUPAC Traditional name: (1S,5S,13R,14S,17R)-10-(^2H₃)methoxy-4-(^2H₃)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-14-ol; phosphoperoxol
• Synonyms: 5α,6α)-4,5-Epoxy-3-(methoxy-d3)-17-(methyl-d3)morphinan-6-ol Phosphate; 7,8-Dihydrocodeine-d6 Phosphate; 8,14-Dihydroneopine-d6 Phosphate; Codhydrine-d6 Phosphate; Cohydrin-d6 Phosphate; DH-Codeine-d6 Phosphate; Dehacodin-d6 Phosphate; Didrate-d6 Phosphate; Dihydrin-d6 Phosphate; Dihydrocodeine-d6 Phosphate; Dihydroneopine-d6 Phosphate; Drocode-d6 Phosphate; Hydrocodeine-d6 Phosphate; Hydrocodin-d6 Phosphate; Nadeine-d6 Phosphate; Novicondin-d6 Phosphate; Paracodin-d6 Phosphate; α-Hydrocodol-d6 Phosphate; Dihydrocodeine-d6 Phosphate

Database IDs

• PubChem SID: 162261691
• PubChem CID: 71316148

CALCULATED PROPERTIES

• Acid pKa: 14.151551
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.7857474
• LogD (pH = 7.4): -0.3756574
• Log P: 1.5489655
• Molar Refractivity: 83.6421 cm^3
• Polarizability: 32.853973 Å^3
• Polar Surface Area: 41.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D448852

Labelled Dihydrocodeine. Opioid Dihydrocodeine compared to cannabinoid Nabilone was effective and tolerable while both drugs showed mild side effects in patient with chronic neuropathic pain. Analgesics.Controlled substance.

REFERENCES

• Notcutt, W., et al.: Pharmaceut. Sci., 3, 551 (1997)
• Hamann, W., et al.: Lancet, 353, 560 (1997)
• Finnerup, N., et al.: Pain, 118, 289 (1997)