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 (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 ~~were~~ found in most plants and animals, ~~they originate~~ from the decarboxylation of 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>

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 ~~inculdes hormons~~ like [[melatonin]] and [[neurotransmitter~~|neurotransmitters~~]] ~~like~~ [[serotonin]]. ~~Pharmacologically, many substituted~~ tryptamines ~~are known for being able~~ to ~~produce~~ [[~~psychedelic~~]] and [[~~entheogen|entheogenic~~]] ~~effects~~. ~~Prominent examples include~~ [[DMT]], [[~~psilocybin~~]], ~~and~~ [[~~ibogaine~~]].

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]]). [[Lysergamides]] can technically be classified as complex tryptamines<ref>https://en.wikipedia.org/wiki/List_of_psychedelic_drugs</ref>, like Ibogaine.

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]], 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==

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

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==

====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'''

|-

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

|-

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

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

|-

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

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

|-

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

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

|-

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

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

|-

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

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

|-

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

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

|-

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

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

|-

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

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

|-

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

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

|-

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

|-

| [[4-AcO-~~DiPT~~]] || ~~Ipracetin~~ || ~~CH(~~CH3~~)2~~ || ~~CH(~~CH3~~)2~~ || OC(O)CH3 || 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-~~DMT~~]] || ~~Psilacetin~~ || CH3 || CH3 || OC(O)CH3 || 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-~~MET~~]] || ~~Metacetin~~ || CH2CH3 || CH3 || OC(O)CH3 || 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-~~DET~~]] || ~~Psilacetin~~ || ~~CH2~~CH3 || CH2CH3 || OC(O)CH3 || 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-~~AcO~~-~~MiPT~~]] || ~~Mipracetin~~ || CH3 ~~|| CH(~~CH3)2 ~~|| OC(O)~~CH3 || 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-~~DET~~]] || ~~Ethacetin~~ || CH2CH3 || CH2CH3 || OH || 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 || OH || H || H || [[File:4-HO-DPT.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 || OH || H || H || [[File:4-HO-MET.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 || OH || H || H || [[File:4-HO-MPT.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 || OH || H || H || [[File:Psilocin.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 || OH || H || H || [[File:4-HO-MiPT.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 || OP(OH)2=O || H || H || [[File:Psilocybin.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 || OH || H || [[File:Serotonin.svg|200px]]

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

|-

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

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

|-

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

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

|-

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

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

|-

| [[5-MeO-DALT]] || || CH2CH=CH2 || CH2CH=CH2 || H || OCH3 || H || [[File:5-MeO-DALT.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 || OCH3 || H || [[File:5-MeO-DiPT.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 || OCH3 || H || [[File:5-MeO-MiPT.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 || [[File:Ibogaine.svg|201px]]

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

|-

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

|[[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}}
+{{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 (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 were found in most plants and animals, they originate from the decarboxylation of 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>
+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 inculdes hormons like [[melatonin]] and [[neurotransmitter|neurotransmitters]] like [[serotonin]]. Pharmacologically, many substituted tryptamines are known for being able to produce [[psychedelic]] and [[entheogen|entheogenic]] effects. Prominent examples include [[DMT]], [[psilocybin]], and [[ibogaine]].
+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]]). [[Lysergamides]] can technically be classified as complex tryptamines<ref>https://en.wikipedia.org/wiki/List_of_psychedelic_drugs</ref>, like Ibogaine.
-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]], 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==
-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 tryptamins" 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.
+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==
-====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'''
+|-
+|[[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]] || || CH<sub>3</sub> || CH<sub>3</sub> || H || H || H || [[File:DMT.svg|200px]]
+|[[DMT]]||Dimethyltryptamine, ''Dmitri'', ''"The Spirit Molecule"''||CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||[[File:DMT.svg|200px]]
 |-
-| [[MET]] || || 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]]
 |-
-| [[DET]] || || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || H || H || H || [[File:DET.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]] || || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || H || H || H || [[File:MPT.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]] || || CH<sub>3</sub> || CH(CH<sub>3</sub>)<sub>2</sub> || H || H || H || [[File:MiPT.svg|200px]]
+|[[MiPT]]||Methylisopropyltryptamine||CH<sub>3</sub>||CH(CH<sub>3</sub>)<sub>2</sub>||H||H||H||[[File:MiPT.svg|200px]]
 |-
-| [[EPT]] || || 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]]
+|[[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]] || || CH(CH<sub>3</sub>)<sub>2</sub> || CH(CH<sub>3</sub>)<sub>2</sub> || H || H || H || [[File:DiPT.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]] || || 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]]
+|[[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]] || || H || H || H || H || CH<sub>3</sub> || [[File:αMT.svg|200px]]
+|[[AMT]]||alpha-methyltryptamine, Indopan||H||H||H||H||CH<sub>3</sub>||[[File:αMT.svg|200px]]
 |}
@@ Line 49: / 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>||H||OC(O)CH<sub>3</sub>||H||H||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> || OC(O)CH<sub>3</sub> || 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-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-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-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-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-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-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-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-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-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-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> || OH || H || H || [[File:4-HO-DPT.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> || OH || H || H || [[File:4-HO-MET.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> || OH || H || H || [[File:4-HO-MPT.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> || OH || H || H || [[File:Psilocin.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> || OH || H || H || [[File:4-HO-MiPT.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> || OP(OH)<sub>2</sub>=O || H || H || [[File:Psilocybin.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 || OH || H || [[File:Serotonin.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 || OH || H || [[File:Bufotenin.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 || OCH<sub>3</sub> || H || [[File:5-MeO-DMT.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 || 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||H||OCH<sub>3</sub>||H||H||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||H||OCH<sub>3</sub>||H||H||H||[[File:5-MeO-DPT.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-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 || 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||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 || OCH<sub>3</sub> || H || [[File:5-MeO-MiPT.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 || [[File:Ibogaine.svg|201px]]
+|[[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]]
 |-
-| [[Melatonin]] || || H || COCH<sub>3</sub> || H || OCH<sub>3</sub> || H || [[File:Melatonin.svg|200px]]
+|[[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 114: / 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 119: / Line 145: @@
 ==References==
 <references />
-[[Category:Tryptamine]]
+[[Category:Tryptamine| ]]
+{{#set:Featured=true}}