Atropine [(±)-Hyoscyamine] and Cocaine (Ornithine-Derived Alkaloids)

Abstract

Atropine (≡ tropine tropate), the major alkaloid of jimson weed, Datura stramonium (Fam. Solanaceae) and the “deadly nightshade,” Atropa belladonna (Fam. Solanaceae), is optically inactive, though it contains a chiral center; hence, it occurs as the racemate. In fact (S)-(–)-hyoscyamine, m.p. 108–111 °C, [α]D –22 (50 % ethanol), present almost exclusively in the optically active form in the fresh leaves of the Datura and Hyoscyamus (H. niger) species (Fam. Solanaceae), partly racemizes to atropine during isolation. Atropine may thus be regarded as (±)-hyoscyamine. Atropa belladonna is associated with an interesting folklore. Fashionable ladies during renaissance used to add a drop of belladonna extract to their eyes to look glossy, bright, and attractive; “bella donna” are Italian words meaning beautiful lady [1].