Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol. It is a poisonous white hygroscopic crystalline powder. It is a heterocyclic alcohol and an amine. Tropine is a central building block of many chemicals active in the nervous system, including tropane alkaloids. Some of these compounds, such as long-acting muscarinic antagonists are used as medicines because of these effects.
Occurrence Tropine is a natural product found in the plants of deadly nightshade (Atropa belladonna) and devil's trumpet (Datura stramonium).
Chemistry
Synthesis It can be prepared by hydrolysis of atropine or other solanaceous alkaloids. In the laboratory it is made by the reduction of tropinone: Patent:
Derivatives List of derivatives that can be made from tropine:
AHN 1-055 HCl: [202646-03-5] Patent: Selfsame as JHW-007 (N-butyl group). This benzhydrol aromatic entity is the same as for flunamine & vanoxerine. Atropine Atromepine Benztropine Bemesetron Butropium bromide (Coliopan®) Ciclotropium (wrong stereochemistry if employing this method) Clobenztropine D-13264 (atropine quat). Decitropine [1242-69-9] Deptropine Fentonium Flutropium bromide (wrong stereoisomer using this method of synthesis). Homatropine PG-9 [156143-26-9] Maleate salt: [155649-00-6] Synthesis: Pharmacol: Methoxytropacin HCl: [74051-44-8] Prampine [7009-65-6] Pudafensine (by Mitsunobu inversion chemistry) SM-21 (other codenames covered too) SM-25 is the ester between tropine and clofibric acid. Tropabazate Tropacine Tropacocaine (by Mitsunobu inversion chemistry) Tropanserin Tropatepine Tropine benzilate ("BAT") Tropirine Tropodifene Xenytropium Zepastine 3-Perfluorophenoxytropane (PC14575207) PC46905316 (Ibuprofen) &PC16115711 (Naproxen). Tropine p-chlorophenoxyacetate [6658-61-3] (c.f. Meclofenoxate).
See also Atropine Pseudotropine Scopine Tropane alkaloid Tropinone
References




