title: Hydrophobic forms of morphine-6-glucosides.
abstract: NMR spectroscopy of 6-acetylmorphine (6-AM), a chloroform-soluble model compound for the hydrophilic, highly potent analgesic drug morphine-6-glucoronide (M6G), in a hydrophobic solvent indicates one hydrogen bonded water molecule per molecule of 6-AM. By analysis of nuclear Overhauser enhancements (NOEs) we find a 6-AM dimer in which the monomers are linked by two water molecules. Molecular modeling studies underscore the stability of such dimeric structures involving water molecules for 6-AM and point out their more lipophilic character allowing penetration of the blood-brain barrier.
authors.affiliation: Institut f. Chemie, Johannes Kepler Universität Linz, A-4040, Linz, Austria.
authors.forename: S
authors.initials: S
authors.lastname: Schwarzinger
authors.forename: M
authors.initials: M
authors.lastname: Hartmann
authors.forename: P
authors.initials: P
authors.lastname: Kremminger
authors.forename: N
authors.initials: N
authors.lastname: Müller
mesh_terms: D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009022:Morphine Derivatives / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D009022:Morphine Derivatives; D014867:Water; C035349:morphine-6-glucuronide; C026979:6-O-monoacetylmorphine