Studies on the synthesis of papaverine.

by Donald Arthur. Guthrie

Institution: McGill University
Department: Department of Chemistry.
Degree: PhD
Year: 1952
Keywords: Chemistry.
Record ID: 1523518
Full text PDF: http://digitool.library.mcgill.ca/thesisfile123982.pdf


Papaverine occurs in the unripe seed capsules of the opium poppy Papaver somniferum, L. in amounts ranging from 0.5 to 1% by weight. Many methods are known to industry for its isolation and purification. This alkaloid finds use in medicine as one of a group of spasmolytic drugs with a paralyzing action on the smooth muscles of the intestines and blood vessels. However, in common with other pharmacologically useful alkaloids derived from the opium poppy, the availability of natural papaverine is ltmited by the stringent international controls on the cultivation of this plant. While several methods have been developed for the synthesis of papaverine, up to this decade, it was doubtful if they could compete economically with even the small yield extracted from natural sources. German research carried out during the last war, and brougnt to light in very recent B.I.O.S. reports, now indicates that synthetic papaverine may compete with, and even displace, the natural product. It seems reasonably certain that any economically successful synthesis of papaverine must employ vanillin as a principal reactant. Althougn vanillin could now be obtained in almost unltmited amounts and at reasonable cost from the waste liquors of the sulfite pulping of softwoods, its production has hitherto been limited by the lack or adequate commercial uses. The present research had the object of exploring still further the possibility of utilizing vanillin for the synthesis of papaverine. [...]