CHAPTER 20: Tryptamines and Lysergamides

Tryptamine (2-(1H-indol-3-yl)ethan-1-amine) is a naturally-occurring metabolite of the amino acid tryptophan, which, in turn, is a constituent of many proteins. Although tryptamine has few significant pharmacological properties, it forms the parent nucleus of a number of hallucinogenic drugs. Some of these tryptamines are derived from plant material or animals and have been used in certain cultures since historical times, for example, N,N-dimethyl tryptamine and its 4-hydroxy and 5-hydroxy derivatives (psilocin and bufotenine respectively). It is clear that the publication of TiHKAL in 1997 generated interest in the potential of many other synthetic tryptamines. Many of these are based on phenyl ring-substitution with hydroxy, alkoxy and methylenedioxy groups and side-chain substitution with alkyl groups. Lysergide (LSD), a more complex structure based on the 2-(1H-indol-3-yl)ethan-1-amine fragment (i.e., tryptamine), was first synthesised by Albert Hofmann in the Sandoz Laboratories in Basel in 1938. Recreational use became popular during the 1960s to 1980s but is now less common in the United Kingdom (UK). Although some tryptamines and lysergamide derivatives are listed by name, many others are covered by separate generic definitions in the UK Misuse of Drugs Act.