Atropine constitution

The family Solanaceae, made up of more than 2,400 species, is especially noteworthy. Many of its members contain the alkaloids atropine (dl-hyoscyamine) and scopolamine (hyosdne). Atropine shows up in mandrake root, henbane and thorn apple it constitutes just over 4.5 percent of the asthmatic preparation called Asthmador. Schultes and Hofmann claim that there are no reports on the effects of atropine alone "which could explain the addition of belladonna as an ingredient of magic brews in medieval Europe. But Hoffer and Osmond recall several historical incidents that attest to its psychoactivity. One story involved a family of five who in 1963 ate tomato plants that had been grafted onto jimson weed, producing 6.36 mg. of atropine per tomato "All five developed deliroid reactions of varying intensity and some had to be treated in the hospital several days. This seems to be the first known instance of hallucinogenic tomatoes. ... 

The isolation of strychnine (1), morphine (2), atropine (3), colchicine (4), and quinine (5) in the early 1800s from the commonly used plants and their use for the treatment of certain ailments might constitute the early idea of pure compounds as drugs. E. Merck isolated and commercialized morphine (2) as the first pure natural product for the treatment of pain (1-3). Preparations of the Willow tree have been used as a painkiller for a long period in traditional medicine. Isolation of salicylic acid (6) as the active component followed by acetylation produced the semisynthetic product called Aspirin (7) that was commercialized by Bayer in 1899 for the treatment of arthritis and pain (4). 

Hyoscyamine and atropine are therefore tropic acid esters of the base tropine. The constitution of tropine according to Willstater is as follows ... 

The constitution of this substance is of great importance, as not only does it show that atropine and hyos-cyamine are represented by the formula— Qg... 

Piperin—CnH,aNOa—an alkaloid of black and white pepper, and isomeric with morphin, is constituted somewhat similarly to atropin. On saponification by alcoholic soda it yields piperidin (see above) and an acid, piperic acid, CuHioO, whose constitution, although partially known, is not completely established. 

Willstatter R (1898a) Ueber die Constitution des Tropins. Ber 30 2679-2719 Willstatter R (1898b) Ueber die Constitution der Spaltungsproducte von Atropin und Cocain. Ber 31 1534-1553... 

---