Substituted tryptamines: Difference between revisions

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[[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]] 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.

'''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>

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]]).

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 ~~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 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==

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==List of substituted tryptamines==

====Ring unsubstituted tryptamines====

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

''Sometimes referred to as "base tryptamines"''.

* [[Lysergamides]]

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

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

{| class="wikitable"

|-

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

|-

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

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

|-

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

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

|-

| [[~~MET~~]] || ~~Methylethyltryptamine~~ || ~~CH2~~CH3 || CH3 || H || H || H || [[File:~~MET~~.svg|200px]]

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

|-

| [[~~DET~~]] || ~~Diethyltryptamine~~ || CH2CH3 || ~~CH2~~CH3 || H || H || H || [[File:~~DET~~.svg|200px]]

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

|-

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

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

|-

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

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

|-

| [[~~EPT~~]] || ~~Ethylpropyltryptamine~~ || CH2CH~~2~~CH3 ~~|| CH~~2~~CH3~~ || H || H || H || [[File:~~EPT~~.svg|200px]]

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

|-

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

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

|-

| [[~~DPT~~]] || ~~Dipropyltryptamine~~ || CH2CH2~~CH3~~ || CH2CH2~~CH3~~ || H || H || H || [[File:~~DPT~~.svg|200px]]

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

|-

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

|}

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{| class="wikitable"

|-

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

|[[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 || OC(O)CH3 || H || H || [[File:4-AcO-DMT.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 || OC(O)CH3 || H || H || [[File:4-AcO-MET.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]] || ~~Psilacetin~~ || CH2CH3 || CH2CH3 || OC(O)CH3 || H || H || [[File:4-AcO-DET.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 || OC(O)CH3 || H || H || [[File:4-AcO-MiPT.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]] || ~~Ethacetin~~ || CH2CH3 || CH2CH3 || OH || H || H || [[File:4-HO-DET.svg|200px]]

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

|-

| [[4-HO-~~DPT~~]] || ~~Procin~~ || CH2CH2CH3 || ~~CH2~~CH2CH3 || OH || H || H || [[File:4-HO-~~DPT~~.svg|200px]]

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

|-

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

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

|-

| [[4-HO-~~MPT~~]] || ~~Meprocin~~ || ~~CH2~~CH2CH3 || CH3 || OH || H || H || [[File:4-HO-~~MPT~~.svg|200px]]

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

|-

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

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

|-

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

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

|-

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

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

|-

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

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

|-

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

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

|-

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

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

|-

| [[5-MeO-~~DET~~]] || || ~~CH2~~CH3 || ~~CH2~~CH3 || H || OCH3 || H || [[File:5-MeO-~~DET~~.svg|200px]]

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

|-

| [[5-MeO-~~DPT~~]] || || ~~CH2~~CH2CH3 || ~~CH2~~CH2CH3 || H || OCH3 || H || [[File:5-MeO-~~DPT~~.svg|200px]]

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

|-

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

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

|-

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

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

|-

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

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

|-

| [[~~Ibogaine~~]] || || CH2CH~~2~~(CH2-)CH2- || ~~CH2(CH-CH3)CH--~~ || H || OCH3 || H || [[File:~~Ibogaine~~.svg|~~201px~~]]

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

|-

| [[Melatonin]] || || H || COCH3 || H || OCH3 || H || [[File:~~Melatonin~~.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]]

|-

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

|}

==See also==

*[[Tryptamine]]

*[[Responsible use]]

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==External links==

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

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

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==References==

[[Category:Tryptamine|*]]

[[Category:Tryptamine| ]]

@@ Line 1: / Line 1: @@
 {{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]] 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.
+'''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>
 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]]).
+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 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 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==
@@ Line 20: / Line 20: @@
 ==List of substituted tryptamines==
-====Ring unsubstituted tryptamines====
+''This table does not include the following groups of substituted tryptamines:''
-''Sometimes referred to as "base tryptamines"''.
+* [[Lysergamides]]
+====Ring-unsubstituted tryptamines====
+''Sometimes referred to as "unsubstituted tryptamines" or "base tryptamines"''
 {| class="wikitable"
 |-
-! scope="col" | '''Compound'''
+! scope="col" |'''Compound'''
-! scope="col" | '''Common name'''
+! scope="col" |'''Common name'''
-! scope="col" style="width: 50px;" | '''R<sub>N1</sub>'''
+! 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>N2</sub>'''
-! scope="col" style="width: 50px;" | '''R<sub>4</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>5</sub>'''
-! scope="col" style="width: 50px;" | '''R<sub>α</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>α</sub>'''
-! scope="col" | '''Structure'''
+! scope="col" |'''Structure'''
 |-
-| NMT || || CH<sub>3</sub> ||H|| H || H || H || [[File:NMT.svg|200px]]
+|[[Tryptamine (compound)|Tryptamine]]||Tryptamine||H||H||H||H||H||[[File:Tryptamine.svg|200px]]
 |-
-| [[DMT]] || Dimethyltryptamine, "Dmitri", "The Spirit Molecule" || CH<sub>3</sub> || CH<sub>3</sub> || H || H || H || [[File:DMT.svg|200px]]
+|NMT||NMT||CH<sub>3</sub>||H||H||H||H||[[File:NMT.svg|200px]]
 |-
-| [[MET]] || Methylethyltryptamine || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || H || H || H || [[File:MET.svg|200px]]
+|[[DMT]]||Dimethyltryptamine, ''Dmitri'', ''"The Spirit Molecule"''||CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||[[File:DMT.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]]
+|[[MET]]||Methylethyltryptamine||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||[[File:MET.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]]
+|[[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]]
 |-
-| [[MiPT]] || Methylisopropyltryptamine  || CH<sub>3</sub> || CH(CH<sub>3</sub>)<sub>2</sub> || H || H || H || [[File:MiPT.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]]
 |-
-| [[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]]
+|[[MiPT]]||Methylisopropyltryptamine||CH<sub>3</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||H||H||[[File:MiPT.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]]
+|[[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]]
 |-
-| [[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]]
+|[[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]]
 |-
-| [[AMT]] || alpha-methyltryptamine, Indopan || H || H || H || H || CH<sub>3</sub> || [[File:αMT.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]]
 |}
@@ Line 57: / Line 61: @@
 {| class="wikitable"
 |-
-! scope="col" | '''Compound'''
+! scope="col" |'''Compound'''
-! scope="col" | '''Common name'''
+! scope="col" |'''Common name'''
-! scope="col" style="width: 50px;" | '''R<sub>N1</sub>'''
+! 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>N2</sub>'''
-! scope="col" style="width: 50px;" | '''R<sub>4</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>2</sub>'''
-! scope="col" style="width: 50px;" | '''R<sub>5</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>4</sub>'''
-! scope="col" style="width: 50px;" | '''R<sub>α</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>5</sub>'''
-! scope="col" | '''Structure'''
+! 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> || OC(O)CH<sub>3</sub> || H || H || [[File:4-AcO-DiPT.svg|200px]]
+|[[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> || OC(O)CH<sub>3</sub> || H || H || [[File:4-AcO-DMT.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> || OC(O)CH<sub>3</sub> || H || H  || [[File:4-AcO-MET.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]] || Psilacetin || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || OC(O)CH<sub>3</sub> || H || H || [[File:4-AcO-DET.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> || OC(O)CH<sub>3</sub> || H || H  || [[File:4-AcO-MiPT.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]] || Ethacetin || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || OH || H || H || [[File:4-HO-DET.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-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> || OH || H || H || [[File:4-HO-DPT.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-MET]] || Metocin || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || OH || H || H || [[File:4-HO-MET.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-MPT]] || Meprocin || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || OH || H || H || [[File:4-HO-MPT.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-DMT]] || Psilocin || CH<sub>3</sub> || CH<sub>3</sub> || OH || H || H || [[File:Psilocin.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-MiPT]] || Miprocin || CH<sub>3</sub> || CH(CH<sub>3</sub>)<sub>2</sub> || OH || H || H || [[File:4-HO-MiPT.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-PO-DMT]] || Psilocybin || CH<sub>3</sub> || CH<sub>3</sub> || OP(OH)<sub>2</sub>=O || H || H || [[File:Psilocybin.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]]
 |-
-| [[Serotonin]] || || H || H || H || OH || H || [[File:Serotonin.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]]
 |-
-| [[5-HO-DMT]] || Bufotenin || CH<sub>3</sub> || CH<sub>3</sub> || H || OH || H || [[File:Bufotenin.svg|200px]]
+|[[Serotonin]]|| ||H||H||H||H||OH||H||H||H||[[File:Serotonin.svg|200px]]
 |-
-| [[5-MeO-DMT]] || || CH<sub>3</sub> || CH<sub>3</sub> || H || OCH<sub>3</sub> || H || [[File:5-MeO-DMT.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-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-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-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-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-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]]
+|[[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-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-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-MiPT]] || Moxy || CH<sub>3</sub> || CH(CH<sub>3</sub>)<sub>2</sub> || H || OCH<sub>3</sub> || H || [[File:5-MeO-MiPT.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]]
 |-
-| [[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 || [[File:Ibogaine.svg|201px]]
+|[[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]]
 |-
-| [[Melatonin]] || || H || COCH<sub>3</sub> || H || OCH<sub>3</sub> || H || [[File:Melatonin.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]]
 |-
-| [[5-HTP]] || || H || H || H || OH || CO<sub>2</sub>H || [[File:5-HTP.svg|200px]]
 |}
 ==See also==
 *[[Tryptamine]]
 *[[Responsible use]]
@@ Line 122: / Line 139: @@
 ==External links==
 *[https://en.wikipedia.org/wiki/Substituted_tryptamine Substituted tryptamine (Wikipedia)]
 *[https://en.wikipedia.org/wiki/List_of_naturally_occurring_tryptamines List of naturally occurring tryptamines (Wikipedia)]
@@ Line 127: / Line 145: @@
 ==References==
 <references />
-[[Category:Tryptamine|*]]
+[[Category:Tryptamine| ]]
+{{#set:Featured=true}}