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Octanol−, Chloroform−, and Propylene Glycol Dipelargonat−Water Partitioning of Morphine-6-glucuronide and Other Related Opiates
- Source :
- Journal of Medicinal Chemistry. 39:4377-4381
- Publication Year :
- 1996
- Publisher :
- American Chemical Society (ACS), 1996.
-
Abstract
- The pKa and log P values of morphine-6-β-d-glucuronide (M6G) and morphine-3-β-d-glucuronide (M3G) and a range of structurally-related opiates (morphine, normorphine, codeine, norcodeine, 6-acetylmorphine, diacetylmorphine, and buprenorphine) were accurately measured using a potentiometric approach. The measured lipophilicity profiles (pH 2−11, 0.15 M KCl matrix) of M3G and M6G were compared using a proton donor solvent (chloroform) and a proton acceptor solvent (propylene glycol dipelargonate, PGDP), in addition to octanol. The log P values and lipophilicity profiles of M6G and M3G determined in octanol−water have confirmed the unexpectedly high lipophilicity of the two glucuronides. These results show the importance of measuring the effect of pH on lipophilicity, since log D (pH 7.4) values gave a notably different order of lipophilicity for the opiates compared with log P. M6G, but not M3G, showed significant differences in log P between different types of partitioning solvents. The observed order of li...
- Subjects :
- Narcotics
Octanol
Octanols
Chemical Phenomena
chemistry.chemical_compound
Norcodeine
Drug Discovery
medicine
Normorphine
Morphine Derivatives
Chloroform
Chromatography
Chemistry, Physical
Biological Transport
Hydrogen-Ion Concentration
Morphine-6-glucuronide
Solutions
Solvent
Partition coefficient
chemistry
Lipophilicity
Potentiometry
Solvents
Molecular Medicine
medicine.drug
Subjects
Details
- ISSN :
- 15204804 and 00222623
- Volume :
- 39
- Database :
- OpenAIRE
- Journal :
- Journal of Medicinal Chemistry
- Accession number :
- edsair.doi.dedup.....dd98be5da89e11f5d515043e2e0a4fcb