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Ibogaine from Trachelospermum |
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Written by (J.A.C.)
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Tuesday, 12 August 1997 |
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"Leaves and stems (50 kg) were dried in the shade and extracted with ethanol. The crude alcoholic extracts were concentrated and partitioned between 10% hydrochloric acid and chloroform (pH 1). The chloroform layer was dried with anhydrous sodium sulfate and concentrated to a gum (25 g, F1). The aqueous acidic layer was basified with aqueous ammonia and extracted into chloroform at various pH values (5, 7, 9, and 11). The fraction obtained at pH-5 (20 g, F2) was found to contain major alkaloids. We have recently reported five indole alkaloids from this plant (2)."
"The crude alkaloidal fraction (F1, 25 g) was subjected to flash chromatography. [...] The alkaloid isolated was identified as voacangine-7-hydroxyindolenine by comparison of its spectral data with those reported in the literature (3). [...] Voacangine-7-hydroxyindolenine may have been formed by air oxidation during the extraction and isolation process." "Fraction F2 (20 g) was also loaded on a silica column (750 g) and was eluted with increasing polarities of mixtures of petroleum ether, chloroform, ethyl acetate, and methanol." "The fraction obtained on elution with chloroform:ethyl acetate (3:1) consisted of a mixture of four alkaloids. This fraction was subjected to a flash chromatography which was eluted with increasing polarities of mixtures of petroleum ether in acetone. The fraction obtained on elution with 70% petroleum ether in acetone was found to contain two major alkaloids. These alkaloids were separated by preparative TLC on silica gel (petroleum ether:acetone:ammonia, 6:3.95:0.05). The faster moving alkaloid was identified as ibogaine by comparison of its spectral data with those reported in the literature (7) while the slower moving alkaloid was identified as tabernaemontanine (8)." "Further elution of the same column with 60% petroleum ether in acetone afforded another alkaloid which was further purified by preparative TLC on silica gel (petroleum ether:acetone:ammonia, 1:1:0 |