1-(1,3-Benzodioxol-5-ylmethyl)-6,7-dimethoxy-4-[(2S)-1-methylpyrrolidin-2-yl]isoquinoline

Description

This newly discovered alkaloid has been isolated from Papaver macrostomum. It crystallizes as colourless rods from C6H6 and is laevorotatory with a specific rotation of [α]²⁵_D - 51 ° ± 3° (c 0.892, CHCI3). It gives a complex ultraviolet spectrum in EtOH with absorption maxima at 241,288,317 and 332 nm with shoulders at 246, 276 and 292 nm. In the presence of dilute acid, these absorption maxima appear at 259, 290 and 319 nm with a shoulder at 333 nm. Macrostomine is found in the non-quaternary fraction of the alkaloidal extract. It gives a negative Cotton effect which leads to the assumption that the configuration is S. The alkaloid forms a crystalline methiodide with m.p. 220-230°C as slender needles when crystallized from EtOH. The structure given has been determined from chemical and spectroscopic data.

References

Minatsakanyan et ai., Tetrahedron Lett., 851 (1974)