Alkaloids: Strychnine, Codeine, Heroin, and Morphine

Research: Science and Education edited by

Featured Molecules

William F. Coleman Wellesley College Wellesley, MA 02481

Alkaloids: Strychnine, Codeine, Heroin, and Morphine September Featured Molecules The featured molecules this month come from the article “The Conversion of Carboxylic Acids to Ketones: A Repeated Discovery” by John W. Nicholson and Alan D. Wilson (pages 1362–1366). The authors describe the repeated “discovery” of this reaction and illustrate its central role in Woodward’s total synthesis of strychnine. Strychnine is a member of a large class of nitrogen heterocycles known as alkaloids, a name derived from the fact that all produce basic solutions in water. Other well-known members of this class of compounds, all of which are pharmacologically active, are nicotine, atropine (deadly nightshade), quinine, lysergic acid, cocaine, and the three structurally similar compounds codeine, heroin, and morphine.

Featured Molecules

Fully manipulable (Chime) versions of these and other molecules are available at the Only@JCE Online Web site: http://www.JCE.DivCHED.org/JCEWWW/Features/ MonthlyMolecules/2004/Sep/

strychnine

an interactive modeling feature, Only@JCE Online

http://www.JCE.DivCHED.org/JCEWWW/Features/MonthlyMolecules

1366

Journal of Chemical Education

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Vol. 81 No. 9 September 2004

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www.JCE.DivCHED.org