Substituted tryptamines: Difference between revisions

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[[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''' (or simply '''tryptamines''') are a group of organic compounds that are based upon the [[tryptamine]] core 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 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 encompasses a variety of biologically important compounds such as hormones like [[melatonin]] and the [[neurotransmitter]] [[serotonin]] (5-hydroxytryptamine).

Many psychoactive tryptamines have been found to occur in nature, although a large number of synthetic variants have been discovered in recent years. Notably, the [[dimethyltryptamine]] (DMT) and [[5-MeO-DMT]] have been found to occur in the human body, although their function is unclear.{{citation needed}}

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]]).

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]].

In terms of [[subjective effects]], psychedelic 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]]). Users tend to report greater amounts of [[Ego loss|ego dissolution]], [[time distortion]], [[conceptual thinking]], and [[transpersonal]] effects such as [[unity and interconnectedness]] with substituted tryptamines. The reason for this is unknown. The subcategory of [[hallucinogens]] known as [[entheogens]] predominantly consist of tryptamines such as [[DMT]] (including [[ayahuasca]]), [[5-MeO-DMT]], and [[psilocybin]].

A systematic investigation of dozens of psychoactive tryptamine compounds was published by Ann and [[Alexander Shulgin]] under the title [[TiHKAL]] ("Tryptamines I Have Known and Loved") in 1997.

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==Chemistry==

The tryptamine core structure consists of an indole ring with attached amino group via a two-carbon sidechain ([[monoamine]] chain) at R3. Ring unsubstituted tryptamines, or so called "base tryptamines", can have various substitutions at the nitrogen (RN1 and RN2) and at Rα. Ring substituted tryptamines can be further substituted at the R4 and R5 positions on the indole ring.

==Pharmacology==

The psychedelic effects of tryptamines are believed to come from their efficacy at the 5-HT2A receptor as a partial [[agonist]]. However, the role of these interactions and how they result in the psychedelic experience is the subject of on-going research.

==List of substituted tryptamines==

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-{{For|the eponymous compound|Tryptamine}}
+{{For|the eponymous compound|Tryptamine (compound)}}
 [[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''' (or simply '''tryptamines''') are a group of organic compounds that are based upon the [[tryptamine]] core 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 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 encompasses a variety of biologically important compounds such as hormones like [[melatonin]] and the [[neurotransmitter]] [[serotonin]] (5-hydroxytryptamine).
+Many psychoactive tryptamines have been found to occur in nature, although a large number of synthetic variants have been discovered in recent years. Notably, the [[dimethyltryptamine]] (DMT) and [[5-MeO-DMT]] have been found to occur in the human body, although their function is unclear.{{citation needed}}
 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]]).
-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]].
+In terms of [[subjective effects]], psychedelic 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]]). Users tend to report greater amounts of [[Ego loss|ego dissolution]], [[time distortion]], [[conceptual thinking]], and [[transpersonal]] effects such as [[unity and interconnectedness]] with substituted tryptamines. The reason for this is unknown. The subcategory of [[hallucinogens]] known as [[entheogens]] predominantly consist of tryptamines such as [[DMT]] (including [[ayahuasca]]), [[5-MeO-DMT]], and [[psilocybin]].
 A systematic investigation of dozens of psychoactive tryptamine compounds was published by Ann and [[Alexander Shulgin]] under the title [[TiHKAL]] ("Tryptamines I Have Known and Loved") in 1997.
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 ==Chemistry==
 The tryptamine core structure consists 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 be further substituted at the R<sub>4</sub> and R<sub>5</sub> positions on the indole ring.
+==Pharmacology==
+{{Further|Serotonergic psychedelic}}
+The psychedelic effects of tryptamines are believed to come from their efficacy at the 5-HT<sub>2A</sub> receptor as a partial [[agonist]]. However, the role of these interactions and how they result in the psychedelic experience is the subject of on-going research.
 ==List of substituted tryptamines==