During the Industrial Revolution, chemists feverishly investigated byproducts of the burgeoning steel and dye industries for possible medical use. At the University of Strasbourg, Paul Hepp and Arnold Cahn were tasked with finding a therapeutic application for naphthalene, a product of coal-tar processing that served as the pungent base of mothballs. Although their compound failed to cure intestinal worms, it still prevailed as an antipyretic, and was hence named Antifebrine. Upon revisiting the ingredients, Hepp and Cahn discovered that odorless acetanilide had accidentally been substituted for potent naphthalene in the original mixture. While Antifebrine was celebrated for its antipyretic and analgesic effects, the remedy fell out of favor after some patients turned blue. Their cyanosis was attributed to methemoglobinemia resulting from aniline, a metabolite of acetanilide. All was not lost, however, as acetaminophen, another acetanilide derivative, was identified as the active ingredient. (Copyright © the American Society of Anesthesiologists’ Wood Library-Museum of Anesthesiology.)

During the Industrial Revolution, chemists feverishly investigated byproducts of the burgeoning steel and dye industries for possible medical use. At the University of Strasbourg, Paul Hepp and Arnold Cahn were tasked with finding a therapeutic application for naphthalene, a product of coal-tar processing that served as the pungent base of mothballs. Although their compound failed to cure intestinal worms, it still prevailed as an antipyretic, and was hence named Antifebrine. Upon revisiting the ingredients, Hepp and Cahn discovered that odorless acetanilide had accidentally been substituted for potent naphthalene in the original mixture. While Antifebrine was celebrated for its antipyretic and analgesic effects, the remedy fell out of favor after some patients turned blue. Their cyanosis was attributed to methemoglobinemia resulting from aniline, a metabolite of acetanilide. All was not lost, however, as acetaminophen, another acetanilide derivative, was identified as the active ingredient. (Copyright © the American Society of Anesthesiologists’ Wood Library-Museum of Anesthesiology.)

Melissa L. Coleman, M.D., Penn State College of Medicine, Hershey, Pennsylvania, and Jane S. Moon, M.D., University of California, Los Angeles, California.