Hydrophobic forms of morphine-6-glucosides.
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.
Schwarzinger
S
S
Institut f. Chemie, Johannes Kepler Universität Linz, A-4040, Linz, Austria.
Hartmann
M
M
Kremminger
P
P
Müller
N
N
D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009022:Morphine Derivatives / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D009022:Morphine Derivatives; D014867:Water; C035349:morphine-6-glucuronide; C026979:6-O-monoacetylmorphine