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Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. [1] Tropane alkaloids occur naturally in many members of the plant family Solanaceae .
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine , among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca ) and Solanaceae (including mandrake , henbane , deadly nightshade , datura , potato , tomato ).
Hyoscyamine (also known as daturine or duboisine) is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna (deadly nightshade).
Of the approximately 200 members in the genus Erythroxylum, most species contain the central nervous system stimulant tropane alkaloid, known more commonly as cocaine.Because the plant is endemic ...
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. [2] [3] Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone. [4]
Atropine, a tropane alkaloid, is an enantiomeric mixture of d-hyoscyamine and l-hyoscyamine [35], with most of its physiological effects due to l-hyoscyamine, the 3(S)-endo isomer of atropine. Its pharmacological effects are due to binding to muscarinic acetylcholine receptors. It is an antimuscarinic agent.
Tropane alkaloid biosynthesis is another avenue of defense with codons positively selected and expanded in the Datura branch. It is aided by the tropane alkaloid Littorine rearrangement which is very important to scopolamine and atropine/hyoscyamine production, all of which serve to debilitate any organism that would come into contact with them.
Ecgonine (tropane derivative) is a tropane alkaloid found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself.