The structure of sanguinarine free base was examined. The base is eith
er bis[6-(5,6-dihydrosanguinarinyl)] ether (3) or bis[6-(5,6-dihydrosa
nguinarinyl)]amine (4) depending on whether Na2CO3 or NH3, respectivel
y, is used as an alkalizing agent. Oxysanguinarine (5) was identified
as a side product formed by disproportionation of the pseudobase inter
mediate 2a.