Metabolism and toxicological analyses of hallucinogenic tryptamine analogues being abused in Japan

Abstract  Hallucinogenic tryptamine analogues, an important class of drugs of abuse, can be naturally occurring or chemically synthesized compounds. In Japan, psilocin and psilocybin (ingredients of “magic mushrooms”) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT; a synthetic tryptamine) seem to be particularly problematic due to their extensive abuse. This review is focused on human metabolism and forensic toxicological analyses of the above three tryptamine analogues. In humans, psilocybin is rapidly dephosphorylated to form psilocin, and most of the psilocin is eventually conjugated to form its glucuronide. On the other hand, 5-MeO-DIPT is mainly metabolized via O-demethylation, 6-hydroxylation, and N-deisopropylation, partly followed by conjugation to form their...