Tropine
Chemical compound
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.
01Occurrence
Tropine is a natural product found in the plants of deadly nightshade (Atropa belladonna) and devil's trumpet (Datura stramonium).
02Chemistry
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:
03Derivatives
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).
Sources and credits
This article is adapted from the Wikipedia article “Tropine”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
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