M.o.M. - Cocaine

The leaves of Erythroxylum coca have been used for stimulant, medicinal and ceremonial purposes by indigenous peoples of South America for Millenia. The tropane alkaloid cocaine (originally called “erythroxyline”) was isolated from Coca in 1855 by chemist Friedrich Gaedcke. In 1860, chemistry PhD student Albert Niemann reported an improved isolation process as part of his dissertation work, and named the molecule “cocaine”. However, the structure remained unknown, until it was elucidated and published in 1901 by organic chemist and future Nobel Prize laureate Richard Willstätter. The cocaine molecule has 4 chiral carbon centers, and when accounting for conformational restriction of the tropane ring, that gives 8 possible stereoisomers! Only one stereoisomer, (R)-(-)-cocaine, is found to a significant degree in Coca and is commonly used by humans. In addition to its stimulant action, cocaine acts as a potent local anesthetic and served as the inspiration for many synthetic local anesthetics including tetracaine and benzocaine. These compounds typically lack the strong stimulant actions of cocaine but retain the local anesthetic action. Interestingly cocaine is still used as a general anesthetic in the United States and elsewhere mostly for ear, nose and throat surgeries.