The Synthesis of n,n-Dimethyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)-ethylamine and of Mesembrine-Like Metabolites of this Potential Analgesic

The synthesis of the analgesic compound N,N-dimethyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)ethylamine ( 1 ) is described. Its structural relation to morphine and its pharmacological activity is shortly discussed. The isolation of three mesembrinelike metabolites of 1 from the plasma of rats is reported along with synthetic work permitting the determination of the relative configuration of these metabolites.