Tropane alkaloids.

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Presentation transcript:

Tropane alkaloids

1- Solanaceous Tropane Alkaloids Occurrence: Atropa, Datura, Hyoscyamus, Duboisia spp. Main Alkaloids are: 1- Atropine. 2- Hyoscyamine. 3. Hyoscine (Scopolamine).

Both alkaloids composed of tropine base and tropic acid. Hyoscyamine is the major natural alkaloid with negative optical rotation (l- form). During extraction hyoscyamine racemizes to the optically inactive dl Atropine. Both alkaloids composed of tropine base and tropic acid. Hyoscyamine

Hyoscine (Scopolamine) Hyoscine is an ester of l-tropic acid with scopoline base. Hyoscine is a syrupy liquid. Hyoscine

P-dimethylaminobenzaldehyde: Vitali-Morin’s test: Solid alkaloid + fuming HNO3 → Evaporate to dryness, dissolve residue in acetoVitali-Morin’s test: Solid alkaloid + fuming HNO3 → Evaporate to dryness, dissolve residue in acetone, add methanolic solution of KOH → Violet colour. P-dimethylaminobenzaldehyde: Alkaloid + reagent in porcelain dish and heat on boiling water path → Intense Red Colour → Cherry Red after cooling. Gerrard’s test: Alkaloid + 2% HgCl2 in 50% Ethanol → Red colour Atropine Red after warming Hyoscyamine White ppt Hyoscine