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Richard Willstätter corrected the structure of cocaine

As a young doctoral student in Munich, Richard Willstätter showed that the accepted chemical structure of cocaine was wrong, launching his career in the chemistry of plant alkaloids.

Richard Willstätter
Richard Willstätter · 1872–1942
Person
Richard Willstätter
Lived
1872–1942
Field
Organic chemistry
From
German

The story

Richard Willstätter entered the University of Munich in 1890, at the age of 18, and came under the influence of Adolf von Baeyer, the leading organic chemist in Germany, who took a close interest in his career. Willstätter never worked directly for Baeyer, but he thought of himself as Baeyer's disciple. In 1893 he began his doctoral research under Alfred Einhorn on the chemistry of cocaine, a plant alkaloid, and he completed his doctorate in 1894.

During that work Willstätter came to suspect that the structure assigned to cocaine, which Einhorn himself had proposed in 1893, was wrong. When Willstätter began independent research, Einhorn forbade him to work on the cocaine problem. With Baeyer's approval, he chose instead to study the closely related compound tropine. Its structure was thought to be similar to that of cocaine, so once tropine was understood, the structure of cocaine could be easily worked out.

Through a series of careful breakdown and synthesis experiments between 1894 and 1898, Willstätter showed that the earlier formulas were incorrect and that these alkaloids belong to a family of compounds built on two linked rings, including a ring of seven atoms. Einhorn was offended and refused to speak to him for the rest of his time in Munich. Willstätter's 1896 habilitation thesis dealt with the tropine group, and in 1897 he applied for a United States patent for tropine ketones and a process for making them. In 1918 he described an elegant synthesis of ecgonine, another member of the family.

The work extended to atropine, another alkaloid from the same family, which is still used in medicine today, for example to treat a slow heart rate and to widen the pupils for eye examinations. His studies of the tropine alkaloids also led him to make cyclooctatetraene, a molecule that became a classic test of chemical theory.

The episode showed the independence of mind that marked Willstätter's whole career. A young doctoral student willing to challenge his own supervisor's formula went on to win the Nobel Prize in Chemistry in 1915, and his early training in alkaloid chemistry prepared him for his great work on the pigments of plants.

Why it matters

Understanding the structures of cocaine and atropine helped chemists design safer local anaesthetics and other medicines based on these molecules.

About Richard Willstätter

Nobel-winning chemist who unravelled chlorophyll and the colours of flowers, refused to convert, resigned his chair in protest at antisemitism and died a refugee in Switzerland.

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Richard Willstätter
1872–1942 · Organic chemistry
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Another act of tikkun olam. This is part of tikkun olam, the Jewish idea of repairing the world, and every one of us can add to it.

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