Alkaloide der Pereiro‐Rinde, IV. Über Geissospermin und Pereirin

Syntheses of tryptamine bases

“…Strong bases were recovered from the aqueous layer by making it strongly alkaline (pH 10 or greater) with sodium hydroxide and extracting continuously for seven days wiuh evhor (4) or tlzcc vdth chicrcfcrrr. (3b), Flavoper eirine was found largely in the latter extracts (3, 4) but was also presentas a contaminant in the fraction of the moderately strong bases (5). Thus, a series of catalytic reductions and a catalytic dehydrogenation, along with a study of the major de hydrogénation product and the ultraviolet spectra of all compounds introduced in the analysis, proved the structure of flavopereirine to be 3-ethylindolo^,3-i7Quinolizine (IE).…”

“…From three to seven kilograms of finely ground bark of G, vellosii or G. laeve were extracted exhaustively with ethanol, either for a week in a soxhlet type of apparatus using 95% ethanol (4) or by leaching an alcoholic paste of the bark with fresh 70% ethanol until 60 liters of extract had been collected (3b)« Non-alkaloidal materials present in the extract could be largely re moved either by allowing the extract to stand five days at 0°C, (4) (thus precipitating about one-half of the material originally extracted) or by evaporating the solvent and treating the residue with dilute sodium hydroxide solution for two days (5). Since later steps in the purification automatically eliminated such impurities, this could be omitted (3b).…”

Syntheses of tryptamine bases

“…Strong bases were recovered from the aqueous layer by making it strongly alkaline (pH 10 or greater) with sodium hydroxide and extracting continuously for seven days wiuh evhor (4) or tlzcc vdth chicrcfcrrr. (3b), Flavoper eirine was found largely in the latter extracts (3, 4) but was also presentas a contaminant in the fraction of the moderately strong bases (5).…”

“…In their attempts to improve the isolation of alkaloids already known to be present in Geissosperraum bark, as well as to analyze further the ex tracts of this bark, two independent groups of workers (3a, 3b, 4) found a new strongly basic orange-colored alkaloid in the bark of two Geissos permum varieties, G, vellosii and G. laeve. In addition, a third group of workers (5) independently isolated this substance as an impurity of a fraction containing the moderately basic alkaloids of the extract. The compound was named flavopereirine (3a) after its deep color and the popu lar Brazilian name -"pao pereira" -given to the tree.…”

“…Non-alkaloidal materials present in the extract could be largely re moved either by allowing the extract to stand five days at 0°C, (4) (thus precipitating about one-half of the material originally extracted) or by evaporating the solvent and treating the residue with dilute sodium hydroxide solution for two days (5). Since later steps in the purification automatically eliminated such impurities, this could be omitted (3b).…”