Indolealkylamine metabolism: synthesis of deuterated indolealkylamines as metabolic probes

The synthesis of the deuterium labeled, endogenously occurring, indolealkylamine hallucinogens N,N-dimethyltryptamine and 5-methoxy-N, N-dimethyltryptamine via reduction of amide intermediates with lithium aluminum deuteride is described. The compounds were characterized with 1H, 2H and 13C NMR. These compounds were synthesized for use as probes for investigating the metabolism of these compounds by MAO via the in vivo kinetic isotope effect. (Author)