Ecgonine

(1R, 2R, 3S, 5S) -3-hydroxy -8-methyl -8 -azabicyclo [ 3.2.1] octane-2 -carboxylic acid

Fixed

Template: Infobox chemical / molecular formula search available

Ecgonine is a tropane alkaloid and is found naturally occurring in the leaves of the coca bush.

Structurally ecgonine is Cycloheptanderivat with a nitrogen bridge. It is obtained by acid or base catalyzed hydrolysis of cocaine and crystallizes with one molecule of water. The crystals melt at 198-199 ° C. Compared to cocaine, it is not addictive and is for the main effect of the common in the Andean countries of chewing coca leaves responsible ( with lime ).

It is a tertiary base, which contains both an acid and alcohol functional group in the molecule. Ecgonine is the corresponding carboxylic acid to pseudotropine ( equatorial position of the hydroxyl group in position 3). By treatment with phosphorus pentachloride anhydroecgonine, C9H13NO2, which is eliminated by heating at 280 ° C with hydrochloric acid and carbon dioxide in tropidine, C8H13N, passes is formed.