Nightshade

Figure 1: Mandragora roots (artist's rendition). The roots of Mandragora species contain hyoscyamine and scopolamine, tropane alkaloids with similar structures, but very different psychoactive effects.

Nightshade. The name conjures fear in many of us… but why? The nightshade family of plants is also called the Solanaceae. Some members of this family produce chemical compounds that are psychoactive in humans (though other members of the Solanaceae are important domesticated food crops, i.e. tomatoes, potatoes, eggplants, etc.). One member of the nightshade family is the Mandragora genus. These plants are also called mandrakes, and truly have roots that look like small humans. Alcoholic extracts from these plants contain hyoscyamine and scopolamine. Hyoscyamine is a central nervous system stimulant, but scopolamine (which differs only in that it contains an additional oxygen atom), is a central nervous system depressant. Plants containing these two compounds have been used for centuries as drugs, poisons, and aphrodisiacs - they appear in Homer’s Odyssey and works by Shakespeare. What would these icons have thought if they had known the uniqueness of these two compounds to the nightshade family and the subtleties of their structures and functions?