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Substituted tryptamines: Difference between revisions
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The chemical class encompasses a variety of biologically important compounds such as hormones like [[melatonin]] and the [[neurotransmitter]] [[serotonin]] (5-hydroxytryptamine). | 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}} | 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]]). | 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]]). [[Lysergamides]] can technically be classified as complex tryptamines<ref>https://en.wikipedia.org/wiki/List_of_psychedelic_drugs</ref>, like Ibogaine. | ||
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]]. | 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. | 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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==List of substituted tryptamines== | ==List of substituted tryptamines== | ||
====Ring unsubstituted tryptamines==== | ====Ring-unsubstituted tryptamines==== | ||
''Sometimes referred to as "base tryptamines"'' | ''Sometimes referred to as "unsubstituted tryptamines" or "base tryptamines"'' | ||
{| class="wikitable" | {| class="wikitable" | ||
|- | |- | ||
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! scope="col" |'''Structure''' | ! scope="col" |'''Structure''' | ||
|- | |- | ||
|[[Tryptamine (compound)|Tryptamine]]|| ||H||H||H||H||H||[[File:Tryptamine.svg|200px]] | |[[Tryptamine (compound)|Tryptamine]]||Tryptamine||H||H||H||H||H||[[File:Tryptamine.svg|200px]] | ||
|- | |- | ||
|NMT|| ||CH<sub>3</sub>||H||H||H||H||[[File:NMT.svg|200px]] | |NMT||NMT||CH<sub>3</sub>||H||H||H||H||[[File:NMT.svg|200px]] | ||
|- | |- | ||
|[[DMT]]||Dimethyltryptamine, | |[[DMT]]||Dimethyltryptamine, ''Dmitri'', ''"The Spirit Molecule"''||CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||[[File:DMT.svg|200px]] | ||
|- | |- | ||
|[[MET]]||Methylethyltryptamine||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||[[File:MET.svg|200px]] | |[[MET]]||Methylethyltryptamine||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||[[File:MET.svg|200px]] | ||
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|[[5-HO-DMT]]||Bufotenin||CH<sub>3</sub>||CH<sub>3</sub>||H||OH||H||[[File:Bufotenin.svg|200px]] | |[[5-HO-DMT]]||Bufotenin||CH<sub>3</sub>||CH<sub>3</sub>||H||OH||H||[[File:Bufotenin.svg|200px]] | ||
|- | |- | ||
|[[5-MeO-DMT]]|| | |[[5-MeO-DMT]]|| ||CH<sub>3</sub>||CH<sub>3</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DMT.svg|200px]] | ||
|CH<sub>3</sub>||CH<sub>3</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DMT.svg|200px]] | |||
|- | |- | ||
|[[5-MeO-DET]]|| ||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DET.svg|200px]] | |[[5-MeO-DET]]|| ||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DET.svg|200px]] | ||
|- | |- | ||
|[[5-MeO-DPT]]|| ||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DPT.svg|200px]] | |[[5-MeO-DPT]]||Foxtrot||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DPT.svg|200px]] | ||
|- | |- | ||
|[[5-MeO-DALT]]|| | |[[5-MeO-DALT]]|| ||CH<sub>2</sub>CH=CH<sub>2</sub>||CH<sub>2</sub>CH=CH<sub>2</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DALT.svg|200px]] | ||
|CH<sub>2</sub>CH=CH<sub>2</sub>||CH<sub>2</sub>CH=CH<sub>2</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DALT.svg|200px]] | |||
|- | |- | ||
|[[5-MeO-DiPT]]||Foxy||CH(CH<sub>3</sub>)<sub>2</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DiPT.svg|200px]] | |[[5-MeO-DiPT]]||Foxy||CH(CH<sub>3</sub>)<sub>2</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DiPT.svg|200px]] | ||