Substituted tryptamines: Difference between revisions

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[[~~Category~~:~~Psychedelic~~]]

[[File:Substituted_tryptamine.svg|thumb|right|299px|Substitutive structure of a ''tryptamine'' molecule]]

'''Substituted tryptamines''' (or simply '''tryptamines''') are a group of organic compounds that are based upon the [[Tryptamine (compound)|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>

[[~~File:SubstitutedTryptamine~~.~~png|thumb|right|288px|General formula~~ of ~~a tryptamine molecule~~.]]

The chemical class encompasses a variety of biologically important compounds such as hormones like [[melatonin]] and the [[neurotransmitter]] [[serotonin]] (5-hydroxytryptamine).

~~'''Substituted Tryptamines''' or '''Tryptamines'''~~ are a class of ~~chemicals that includes compounds~~ with psychoactive ~~effects~~.

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]]). [[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]].

A systematic investigation of 55 psychoactive tryptamine and lysergamide compounds was published by Ann and [[Alexander Shulgin]] under the title [[TiHKAL]] ("Tryptamines I Have Known and Loved") in 1997.

==Chemistry==

~~Tryptamines are a chemical class based upon the molecule~~ tryptamine~~. Tryptamine is made up~~ of an indole ring attached to a monoamine chain. ~~The chemical structure of a tryptamine-class molecule is the same as tryptamine~~, ~~except some of~~ the ~~hydrogen atoms are~~ substituted ~~for a different functional groups~~.

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 ~~tryptamine class~~ of psychedelic ~~drugs works via their action upon~~ the [[Serotonin~~#The~~ 5-~~HT System~~|5-HT2A ~~receptor~~]].

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==

''This table does not include the following groups of substituted tryptamines:''

* [[Lysergamides]]

====Ring-unsubstituted tryptamines====

''Sometimes referred to as "unsubstituted tryptamines" or "base tryptamines"''

{| class="wikitable"

|-

! scope="col" |'''Compound'''

! scope="col" |'''Common name'''

! scope="col" style="width: 50px;" |'''RN1'''

! scope="col" style="width: 50px;" |'''RN2'''

! scope="col" style="width: 50px;" |'''R4'''

! scope="col" style="width: 50px;" |'''R5'''

! scope="col" style="width: 50px;" |'''Rα'''

! scope="col" |'''Structure'''

|-

|[[Tryptamine (compound)|Tryptamine]]||Tryptamine||H||H||H||H||H||[[File:Tryptamine.svg|200px]]

|-

|NMT||NMT||CH3||H||H||H||H||[[File:NMT.svg|200px]]

|-

|[[DMT]]||Dimethyltryptamine, ''Dmitri'', ''"The Spirit Molecule"''||CH3||CH3||H||H||H||[[File:DMT.svg|200px]]

|-

|[[MET]]||Methylethyltryptamine||CH2CH3||CH3||H||H||H||[[File:MET.svg|200px]]

|-

|[[DET]]||Diethyltryptamine||CH2CH3||CH2CH3||H||H||H||[[File:DET.svg|200px]]

|-

|[[MPT]]||Methylpropyltryptamine||CH2CH2CH3||CH3||H||H||H||[[File:MPT.svg|200px]]

|-

|[[MiPT]]||Methylisopropyltryptamine||CH3||CH(CH3)2||H||H||H||[[File:MiPT.svg|200px]]

|-

|[[EPT]]||Ethylpropyltryptamine||CH2CH2CH3||CH2CH3||H||H||H||[[File:EPT.svg|200px]]

|-

|[[DiPT]]||Diisopropyltryptamine||CH(CH3)2||CH(CH3)2||H||H||H||[[File:DiPT.svg|200px]]

|-

|[[DPT]]||Dipropyltryptamine||CH2CH2CH3||CH2CH2CH3||H||H||H||[[File:DPT.svg|200px]]

|-

|[[AMT]]||alpha-methyltryptamine, Indopan||H||H||H||H||CH3||[[File:αMT.svg|200px]]

|}

====Ring substituted tryptamines====

{| class="wikitable"

|-

! scope="col" |'''Compound'''

! scope="col" |'''Common name'''

! scope="col" style="width: 50px;" |'''RN1'''

! scope="col" style="width: 50px;" |'''RN2'''

! scope="col" style="width: 50px;" |'''R2'''

! scope="col" style="width: 50px;" |'''R4'''

! scope="col" style="width: 50px;" |'''R5'''

! scope="col" style="width: 50px;" |'''R6'''

! scope="col" style="width: 50px;" |'''Rα'''

! scope="col" style="width: 50px;" |'''Rβ'''

! scope="col" |'''Structure'''

|-

|[[4-AcO-DiPT]]||Ipracetin||CH(CH3)2||CH(CH3)2||H||OC(O)CH3||H||H||H||H||[[File:4-AcO-DiPT.svg|200px]]

|-

|[[4-AcO-DMT]]||Psilacetin||CH3||CH3||H||OC(O)CH3||H||H||H||H||[[File:4-AcO-DMT.svg|200px]]

|-

|[[4-AcO-MET]]||Metacetin||CH2CH3||CH3||H||OC(O)CH3||H||H||H||H||[[File:4-AcO-MET.svg|200px]]

|-

|[[4-AcO-DET]]||Ethacetin||CH2CH3||CH2CH3||H||OC(O)CH3||H||H||H||H||[[File:4-AcO-DET.svg|200px]]

|-

|[[4-AcO-MiPT]]||Mipracetin||CH3||CH(CH3)2||H||OC(O)CH3||H||H||H||H||[[File:4-AcO-MiPT.svg|200px]]

|-

|[[4-HO-DET]]||Ethocin||CH2CH3||CH2CH3||H||OH||H||H||H||H||[[File:4-HO-DET.svg|200px]]

|-

|[[4-HO-EPT]]||Eprocin||CH2CH2CH3||CH2CH3||H||OH||H||H||H||H||[[File:4-HO-EPT.svg|200px]]

|-

|[[4-HO-DPT]]||Procin||CH2CH2CH3||CH2CH2CH3||H||OH||H||H||H||H||[[File:4-HO-DPT.svg|200px]]

|-

|[[4-HO-MET]]||Metocin||CH2CH3||CH3||H||OH||H||H||H||H||[[File:4-HO-MET.svg|200px]]

|-

|[[4-HO-MPT]]||Meprocin||CH2CH2CH3||CH3||H||OH||H||H||H||H||[[File:4-HO-MPT.svg|200px]]

|-

|[[4-HO-DMT]]||Psilocin||CH3||CH3||H||OH||H||H||H||H||[[File:Psilocin.svg|200px]]

|-

|[[4-HO-MiPT]]||Miprocin||CH3||CH(CH3)2||H||OH||H||H||H||H||[[File:4-HO-MiPT.svg|200px]]

|-

|[[4-PO-DMT]]||Psilocybin||CH3||CH3||H||OP(OH)2=O||H||H||H||H||[[File:Psilocybin.svg|200px]]

|-

|[[Serotonin]]|| ||H||H||H||H||OH||H||H||H||[[File:Serotonin.svg|200px]]

|-

|[[5-HO-DMT]]||Bufotenin||CH3||CH3||H||H||OH||H||H||H||[[File:Bufotenin.svg|200px]]

|-

|[[5-MeO-DMT]]|| ||CH3||CH3||H||H||OCH3||H||H||H||[[File:5-MeO-DMT.svg|200px]]

|-

|[[5-MeO-DET]]|| ||CH2CH3||CH2CH3||H||H||OCH3||H||H||H||[[File:5-MeO-DET.svg|200px]]

|-

|[[5-MeO-DPT]]||Foxtrot||CH2CH2CH3||CH2CH2CH3||H||H||OCH3||H||H||H||[[File:5-MeO-DPT.svg|200px]]

|-

|[[5-MeO-DALT]]||Foxtrot||CH2CH=CH2||CH2CH=CH2||H||H||OCH3||H||H||H||[[File:5-MeO-DALT.svg|200px]]

|-

|[[5-MeO-DiPT]]||Foxy||CH(CH3)2||CH(CH3)2||H||H||OCH3||H||H||H||[[File:5-MeO-DiPT.svg|200px]]

|-

|[[5-MeO-MiPT]]||Moxy||CH3||CH(CH3)2||H||H||OCH3||H||H||H||[[File:5-MeO-MiPT.svg|200px]]

|-

|[[Ibogaine]]|| ||CH2CH2(CH2-)CH2-||CH2(CH-CH3)CH--||-||H||OCH3||H||H||H||[[File:Ibogaine.svg|201px]]

|-

|[[5-HTP]]|| ||H||H||H||H||OH||H||CO2H||H||[[File:5-HTP.svg|200px]]

|-

|[[Melatonin]]|| ||COCH3||H||H||H||OCH3||H||H||H||[[File:Melatonin.svg|200px]]

|-

|TIK-301|| ||COCH3||H||H||H||OCH3||Cl||H||CH3||[[File:TIK-301.svg|200px]]

|-

|Pericine|| ||CH2C(CHCH3)-||CH2CH2-||C(CH2)-||H||H||H||H||H||[[File:Pericine.svg|200px]]

|-

|Carbazocine|| ||CH2C3H5||CH2CH2-||-||H||H||H||CH-(CH2CH2CH2CH2-)||H||[[File:Carbazocine.svg|200px]]

|-

|}

==See also==

~~==Examples==~~

*[[Tryptamine]]

~~Tryptamines are seen throughout organic chemistry and include~~ [[~~neurotransmitter|neurotransmitters~~]] ~~and psychoactive drugs.~~

*[[Responsible use]]

*[[Lysergamide]]

*[[TiHKAL]]

*[[Entheogen]]

*[[Phenethylamine]]

~~'''Neurotransmitters/[[Hormone|Hormones]]'''~~

==External links==

*[[Serotonin]]

*[[Melatonin]]

~~'''Psychedelic Drugs'''~~

*[https://en.wikipedia.org/wiki/Substituted_tryptamine Substituted tryptamine (Wikipedia)]

*[~~[DMT]]~~/~~[[Ayahuasca]~~]

*[https://en.wikipedia.org/wiki/List_of_naturally_occurring_tryptamines List of naturally occurring tryptamines (Wikipedia)]

*[~~[Psilocin]]~~

*[[Psilocetin|4-AcO-DMT]]

*[[AMT]]

*[[5-MeO-DMT]]

*[[Bufotenin]]

==~~See Also~~==

==References==

*[[Psychedelics]]

*[[Lysergamides]]

[[Category:Tryptamine| ]]

*[[Phenethylamines]]

*[[~~Beta-Carbolines~~]]

~~[[Category~~:~~Psychedelics]]~~

@@ Line 1: / Line 1: @@
-[[Category:Psychedelic]]
+{{For|the eponymous compound|Tryptamine (compound)}}
+[[File:Substituted_tryptamine.svg|thumb|right|299px|Substitutive structure of a ''tryptamine'' molecule]]
+'''Substituted tryptamines''' (or simply '''tryptamines''') are a group of organic compounds that are based upon the [[Tryptamine (compound)|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>
-[[File:SubstitutedTryptamine.png|thumb|right|288px|General formula of a tryptamine molecule.]]
+The chemical class encompasses a variety of biologically important compounds such as hormones like [[melatonin]] and the [[neurotransmitter]] [[serotonin]] (5-hydroxytryptamine).
-'''Substituted Tryptamines''' or '''Tryptamines''' are a class of chemicals that includes compounds with psychoactive effects.
+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]]). [[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]].
+A systematic investigation of 55 psychoactive tryptamine and lysergamide compounds was published by Ann and [[Alexander Shulgin]] under the title [[TiHKAL]] ("Tryptamines I Have Known and Loved") in 1997.
 ==Chemistry==
-Tryptamines are a chemical class based upon the molecule tryptamine. Tryptamine is made up of an indole ring attached to a monoamine chain. The chemical structure of a tryptamine-class molecule is the same as tryptamine, except some of the hydrogen atoms are substituted for a different functional groups.
+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==
-The tryptamine class of psychedelic drugs works via their action upon the [[Serotonin#The 5-HT System|5-HT<sub>2A</sub> receptor]].
+{{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==
+''This table does not include the following groups of substituted tryptamines:''
+* [[Lysergamides]]
+====Ring-unsubstituted tryptamines====
+''Sometimes referred to as "unsubstituted tryptamines" or "base tryptamines"''
+{| class="wikitable"
+|-
+! scope="col" |'''Compound'''
+! scope="col" |'''Common name'''
+! scope="col" style="width: 50px;" |'''R<sub>N1</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>N2</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>4</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>5</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>α</sub>'''
+! scope="col" |'''Structure'''
+|-
+|[[Tryptamine (compound)|Tryptamine]]||Tryptamine||H||H||H||H||H||[[File:Tryptamine.svg|200px]]
+|-
+|NMT||NMT||CH<sub>3</sub>||H||H||H||H||[[File:NMT.svg|200px]]
+|-
+|[[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]]
+|-
+|[[DET]]||Diethyltryptamine||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||H||H||[[File:DET.svg|200px]]
+|-
+|[[MPT]]||Methylpropyltryptamine||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||[[File:MPT.svg|200px]]
+|-
+|[[MiPT]]||Methylisopropyltryptamine||CH<sub>3</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||H||H||[[File:MiPT.svg|200px]]
+|-
+|[[EPT]]||Ethylpropyltryptamine||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||H||H||[[File:EPT.svg|200px]]
+|-
+|[[DiPT]]||Diisopropyltryptamine||CH(CH<sub>3</sub>)<sub>2</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||H||H||[[File:DiPT.svg|200px]]
+|-
+|[[DPT]]||Dipropyltryptamine||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||H||H||[[File:DPT.svg|200px]]
+|-
+|[[AMT]]||alpha-methyltryptamine, Indopan||H||H||H||H||CH<sub>3</sub>||[[File:αMT.svg|200px]]
+|}
+====Ring substituted tryptamines====
+{| class="wikitable"
+|-
+! scope="col" |'''Compound'''
+! scope="col" |'''Common name'''
+! scope="col" style="width: 50px;" |'''R<sub>N1</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>N2</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>2</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>4</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>5</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>6</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>α</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>β</sub>'''
+! scope="col" |'''Structure'''
+|-
+|[[4-AcO-DiPT]]||Ipracetin||CH(CH<sub>3</sub>)<sub>2</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||OC(O)CH<sub>3</sub>||H||H||H||H||[[File:4-AcO-DiPT.svg|200px]]
+|-
+|[[4-AcO-DMT]]||Psilacetin||CH<sub>3</sub>||CH<sub>3</sub>||H||OC(O)CH<sub>3</sub>||H||H||H||H||[[File:4-AcO-DMT.svg|200px]]
+|-
+|[[4-AcO-MET]]||Metacetin||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>3</sub>||H||OC(O)CH<sub>3</sub>||H||H||H||H||[[File:4-AcO-MET.svg|200px]]
+|-
+|[[4-AcO-DET]]||Ethacetin||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||OC(O)CH<sub>3</sub>||H||H||H||H||[[File:4-AcO-DET.svg|200px]]
+|-
+|[[4-AcO-MiPT]]||Mipracetin||CH<sub>3</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||OC(O)CH<sub>3</sub>||H||H||H||H||[[File:4-AcO-MiPT.svg|200px]]
+|-
+|[[4-HO-DET]]||Ethocin||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||OH||H||H||H||H||[[File:4-HO-DET.svg|200px]]
+|-
+|[[4-HO-EPT]]||Eprocin||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||OH||H||H||H||H||[[File:4-HO-EPT.svg|200px]]
+|-
+|[[4-HO-DPT]]||Procin||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||OH||H||H||H||H||[[File:4-HO-DPT.svg|200px]]
+|-
+|[[4-HO-MET]]||Metocin||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>3</sub>||H||OH||H||H||H||H||[[File:4-HO-MET.svg|200px]]
+|-
+|[[4-HO-MPT]]||Meprocin||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||CH<sub>3</sub>||H||OH||H||H||H||H||[[File:4-HO-MPT.svg|200px]]
+|-
+|[[4-HO-DMT]]||Psilocin||CH<sub>3</sub>||CH<sub>3</sub>||H||OH||H||H||H||H||[[File:Psilocin.svg|200px]]
+|-
+|[[4-HO-MiPT]]||Miprocin||CH<sub>3</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||OH||H||H||H||H||[[File:4-HO-MiPT.svg|200px]]
+|-
+|[[4-PO-DMT]]||Psilocybin||CH<sub>3</sub>||CH<sub>3</sub>||H||OP(OH)<sub>2</sub>=O||H||H||H||H||[[File:Psilocybin.svg|200px]]
+|-
+|[[Serotonin]]|| ||H||H||H||H||OH||H||H||H||[[File:Serotonin.svg|200px]]
+|-
+|[[5-HO-DMT]]||Bufotenin||CH<sub>3</sub>||CH<sub>3</sub>||H||H||OH||H||H||H||[[File:Bufotenin.svg|200px]]
+|-
+|[[5-MeO-DMT]]|| ||CH<sub>3</sub>||CH<sub>3</sub>||H||H||OCH<sub>3</sub>||H||H||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||H||OCH<sub>3</sub>||H||H||H||[[File:5-MeO-DET.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||H||OCH<sub>3</sub>||H||H||H||[[File:5-MeO-DPT.svg|200px]]
+|-
+|[[5-MeO-DALT]]||Foxtrot||CH<sub>2</sub>CH=CH<sub>2</sub>||CH<sub>2</sub>CH=CH<sub>2</sub>||H||H||OCH<sub>3</sub>||H||H||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||H||OCH<sub>3</sub>||H||H||H||[[File:5-MeO-DiPT.svg|200px]]
+|-
+|[[5-MeO-MiPT]]||Moxy||CH<sub>3</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||H||OCH<sub>3</sub>||H||H||H||[[File:5-MeO-MiPT.svg|200px]]
+|-
+|[[Ibogaine]]|| ||CH<sub>2</sub>CH<sub>2</sub>(CH<sub>2</sub>-)CH<sub>2</sub>-||CH<sub>2</sub>(CH-CH<sub>3</sub>)CH--||-||H||OCH<sub>3</sub>||H||H||H||[[File:Ibogaine.svg|201px]]
+|-
+|[[5-HTP]]|| ||H||H||H||H||OH||H||CO<sub>2</sub>H||H||[[File:5-HTP.svg|200px]]
+|-
+|[[Melatonin]]|| ||COCH<sub>3</sub>||H||H||H||OCH<sub>3</sub>||H||H||H||[[File:Melatonin.svg|200px]]
+|-
+|TIK-301|| ||COCH<sub>3</sub>||H||H||H||OCH<sub>3</sub>||Cl||H||CH<sub>3</sub>||[[File:TIK-301.svg|200px]]
+|-
+|Pericine|| ||CH<sub>2</sub>C(CHCH<sub>3</sub>)-||CH<sub>2</sub>CH<sub>2</sub>-||C(CH<sub>2</sub>)-||H||H||H||H||H||[[File:Pericine.svg|200px]]
+|-
+|Carbazocine|| ||CH<sub>2</sub>C<sub>3</sub>H<sub>5</sub>||CH<sub>2</sub>CH<sub>2</sub>-||-||H||H||H||CH-(CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>-)||H||[[File:Carbazocine.svg|200px]]
+|-
+|}
+==See also==
-==Examples==
+*[[Tryptamine]]
-Tryptamines are seen throughout organic chemistry and include [[neurotransmitter|neurotransmitters]] and psychoactive drugs.
+*[[Responsible use]]
+*[[Lysergamide]]
+*[[TiHKAL]]
+*[[Entheogen]]
+*[[Phenethylamine]]
-'''Neurotransmitters/[[Hormone|Hormones]]'''
+==External links==
-*[[Serotonin]]
-*[[Melatonin]]
-'''Psychedelic Drugs'''
+*[https://en.wikipedia.org/wiki/Substituted_tryptamine Substituted tryptamine (Wikipedia)]
-*[[DMT]]/[[Ayahuasca]]
+*[https://en.wikipedia.org/wiki/List_of_naturally_occurring_tryptamines List of naturally occurring tryptamines (Wikipedia)]
-*[[Psilocin]]
-*[[Psilocetin|4-AcO-DMT]]
-*[[AMT]]
-*[[5-MeO-DMT]]
-*[[Bufotenin]]
-==See Also==
+==References==
-*[[Psychedelics]]
+<references />
-*[[Lysergamides]]
+[[Category:Tryptamine| ]]
-*[[Phenethylamines]]
-*[[Beta-Carbolines]]
-[[Category:Psychedelics]]
+{{#set:Featured=true}}