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Substituted tryptamines: Difference between revisions
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[[File:Substituted_tryptamine.svg|thumb|right|299px|Substitutive structure of a ''tryptamine'' molecule]] | [[File:Substituted_tryptamine.svg|thumb|right|299px|Substitutive structure of a ''tryptamine'' molecule]] | ||
'''Substituted tryptamines''' (also referred to as '''tryptamines''') are a group of organic compounds that are based upon the [[tryptamine]] structure. The class is composed of all the derivative compounds which can be formed by substituting one or more hydrogen atoms in the tryptamine core structure with other substituents. | '''Substituted tryptamines''' (also referred to as '''tryptamines''') are a group of organic compounds that are based upon the [[tryptamine]] structure. The class is composed of all the derivative compounds which can be formed by substituting one or more hydrogen atoms in the tryptamine core structure with other substituents. | ||
Natural tryptamines | Natural tryptamines are found in most plants and animals, forming from the decarboxylation of the amino acid tryptophan.<ref>{{cite web|title=Tryptamines|url=https://www.sciencedirect.com/topics/neuroscience/tryptamines|archive-url=https://web.archive.org/web/20200110234704/https://www.sciencedirect.com/topics/neuroscience/tryptamines|access-date=January 11, 2020|archive-date=January 11, 2020|publisher=ScienceDirect}}</ref> | ||
The chemical class | The chemical class encompasses a variety of biologically important compounds such as hormones like [[melatonin]] and the [[neurotransmitter]] [[serotonin]] (5-hydroxytryptamine). | ||
Most of the known substituted tryptamines act as psychedelics (e.g. [[psilocybin]], [[DMT]], [[ibogaine]]), although there are some that have [[entactogenic]] properties (e.g. [[aMT]], [[5-MeO-MiPT]]). | |||
An investigation of dozens of psychoactive tryptamine compounds was published by Ann and [[Alexander Shulgin]] under the name [[TiHKAL]] in 1997. | In terms of [[subjective effects]], substituted tryptamines are generally regarded as producing a significantly stronger and "deeper" psychedelic effect than the other major class of psychedelics, the substituted phenethylamines (e.g. [[mescaline]] or the [[2C-x family]]). The subcategory of [[hallucinogens]] known as [[entheogens]] predominantly consist of substituted tryptamines such as [[DMT]] (including [[ayahuasca]]), [[5-MeO-DMT]] and [[psilocybin]]. | ||
An investigation of dozens of psychoactive tryptamine compounds was published by Ann and [[Alexander Shulgin]] under the name [[TiHKAL]] ("Tryptamines I Have Known and Loved") in 1997. | |||
==Chemistry== | ==Chemistry== | ||
The structure of any substituted tryptamine is comprised of an indole ring with attached amino group via a two-carbon sidechain ([[monoamine]] chain) at R<sub>3</sub>. Ring unsubstituted tryptamines or so called "base | The structure of any substituted tryptamine is comprised of an indole ring with attached amino group via a two-carbon sidechain ([[monoamine]] chain) at R<sub>3</sub>. Ring unsubstituted tryptamines or so called "base tryptamines" can have various substitutions at the nitrogen (R<sub>N1</sub> and R<sub>N2</sub>) and at R<sub>α</sub>. Ring substituted tryptamines can furthermore be substituted at the R<sub>4</sub> and R<sub>5</sub> positions at the indole ring. | ||
==List of substituted tryptamines== | ==List of substituted tryptamines== | ||