Protopine hydrochloride (5,6,14,14a-tetrahydro-14a-hydroxy7-methyl-8H-bis[1
,3]benzodioxolo[5,6-a:4,5-g]quinolizinium chloride, C20H20NO5+. Cl-) is the
salt of the isoquinoline alkaloid protopine. It is formed by the action of
dilute hydrochloric acid on the protopine free base. The N-methyl and hydr
oxyl groups are in a trans configuration in the quinolizine ring and the ce
ntral quinolizine N-C bond is unusually long [1.579 (2) Angstrom ]. The cry
stal is a racemate.