(S)-l,10-Dimethoxy-2,9-dihydroxyaporphinium Chloride (Boldine Hydrochloride), C19H22NO4+.Cl -

Abstract

Boldine (5,6,6a,7-tetrahydro- 1,10-dimethoxy-6-methyl- 4H-dibenzo[de,g]quinoline-2,9-diol) is an aporphine alkaloid noted for its antioxidant properties. A salient feature of the molecule is the non-planarity of the biphenyl system, which exhibits a dihedral angle of 151.1 (8) ° between the least-squares planes of the two benzenoid rings and torsion angles of 25.7 (3), - 150.6 (2), - 155.9 (2) and 27.8 (3) ° about the biphenyl bond. Methoxy C atom C 13 lies only 0.195 (4) A above the mean plane of the ring to which it is attached, with torsion angles about the C10--O2 bond of 168.6 (2) and -11.344) °. Methoxy C atom C14 is displaced -1.101 (3)A from the corresponding ring plane, with torsion angles about the C1---O3 bond of 102.3 (2) and -79.7 (3) °. All intramolecular bonds and angles are within the expected range.