Tryptamines and Lysergamides
Royal Society of Chemistry eBooks July 22, 2022 DOI: 10.1039/9781839166631-00257 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Review Peer reviewed |
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| Key findings | Tryptamine is the parent nucleus of several hallucinogenic drugs, including plant- and animal-derived compounds used in some cultures since historical times and many synthetic tryptamines that drew interest after the 1997 publication of TiHKAL. LSD, a more complex tryptamine-based structure, was first synthesized by Albert Hofmann in 1938. Recreational use peaked in the 1960s to 1980s and is now less common in the UK, where some tryptamines and lysergamide derivatives are named in the Misuse of Drugs Act and many others are covered by generic definitions. |
Abstract
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.