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Listerine, a mouthrinse composed of a mixture of essential oils, was created in 1879 and was originally formulated as a surgical antiseptic. In spite of its known antimicrobial properties it was thought of as a product in search of a use and promoted as a deterrent for halitosis and as a floor cleaner. In the last several years Listerine has emerged as a bona fide therapeutic agent for reduction of plaque induced oral diseases. In contrast to the inconsistent history of Listerine, systemic antibiotics discovered in the 1940's were heralded as miracle drugs. However, the value of prophylactic usage of antibiotics has come under scrutiny as a result of increasing resistance and adverse reactions. Moreover, reports by both American and British professional societies have led to a re-evaluation of the relative risks associated with plaque induced bacteremia when twice-yearly visits to dental professionals are compared to daily activities. These new recommendations and revelations open the door for local antimicrobial approaches to reduce the challenge of plaque-induced bacteremias. These issues will be discussed in the context of Listerine, its intricate and complicated past, and its connection to current uses in oral health and beyond.

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Vicks VapoRub (Procter & Gamble, Cincinnati, OH) is one of the most popular over-the-counter therapies in the world, used to provide relief from the symptoms of the common cold and non-life-threatening respiratory infections. Even as more advanced products have come and gone, VapoRub continues to dominate the market almost 9 decades after the death of its formulator, Lunsford Richardson (Figure).

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Ginkgolides were always close to my heart. I continue to be strongly attracted to Ginkgo biloba, the ginkgolides and bilobalide. Starting in 1963, I became fascinated by these molecules while working on their isolation and structure elucidation in Sendai. Presumably, due to the ginkgolide studies, I received an invitation to join the faculty at Columbia University. After almost three decades of not touching the ginkgolide project, we have unexpectedly resumed the studies, at this time because of their enigmatic biological effects. This account is a reflection on earlier studies, as well as an outline of our current work.

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Camphor, alpha-pinene (the major component of turpentine), and thujone (a constituent in the liqueur called absinthe) produced an increase in porphyrin production in primary cultures of chick embryo liver cells. In the presence of desferrioxamine (an iron chelator which inhibits heme synthesis and thereby mimics the effect of the block associated with acute porphyria), the terpenes enhanced porphyrin accumulation 5- to 20-fold. They also induced synthesis of the rate-controlling enzyme for the pathway, 5-aminolevulinic acid synthase, which was monitored both spectrophotometrically and immunochemically. These effects are shared by well-known porphyrogenic chemicals such as phenobarbital and glutethimide. Camphor and glutethimide alone led to the accumulation of mostly uro- and heptacarboxylporphyrins, whereas alpha-pinene and thujone resulted in lesser accumulations of porphyrins which were predominantly copro- and protoporphyrins. In the presence of desferrioxamine, plus any of the three terpenes, the major product that accumulated was protoporphyrin. The present results indicate that the terpenes tested are porphyrogenic and hazardous to patients with underlying defects in hepatic heme synthesis. There are also implications for the illness of Vincent van Gogh and the once popular, but now banned liqueur, called absinthe.

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During his last two years Vincent van Gogh experienced fits with hallucinations that have been attributed to a congenital psychosis. But the artist admitted to episodes of heavy drinking that were amply confirmed by colleagues and there is good evidence to indicate that addiction to absinthe exacerbated his illness. Absinthe was distilled from an alcoholic steep of herbs. Wormwood (Artemisia absinthium) was the most significant constituent because it contributed thujone. This terpene can cause excitation, convulsions that mimic epilepsy, and even permanent brain damage. Statements in van Gogh's letters and from his friends indicate that he had an affinity for substances with a chemical connection to thujone; the documented examples are camphor and pinene. Perhaps he developed an abnormal craving for terpenes, a sort of pica, that would explain his attempts to eat paints and so on, which were previously regarded as unrelated absurdities.

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