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).

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'''

|-

| [[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 || || CH3 ||H|| H || H || H || [[File:NMT.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]]

|[[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]]

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

|-

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

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

|-

| [[MPT]] || Methylpropyltryptamine || CH2CH2CH3 || CH3 || H || H || H || [[File:MPT.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]]

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

|-

| [[EPT]] || Ethylpropyltryptamine || CH2CH2CH3 || CH2CH3 || H || H || H || [[File:EPT.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]]

|[[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]]

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

|-

| [[AMT]] || alpha-methyltryptamine, Indopan || 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 || 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]] || Ethacetin || 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]] || Ethocin || 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-EPT]] || Eprocin || CH2CH2CH3 || CH2CH3 || OH || H || H || [[File:4-HO-EPT.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]] || Foxtrot || 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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[[Category:Tryptamine| ]]

@@ Line 6: / Line 6: @@
 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'''
 |-
-| [[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, "Dmitri", "The Spirit Molecule" || 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]] || 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]]
 |-
-| [[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]]
+|[[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]]
+|[[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]]
+|[[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]]
+|[[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]]
+|[[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]]
+|[[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]]
+|[[AMT]]||alpha-methyltryptamine, Indopan||H||H||H||H||CH<sub>3</sub>||[[File:αMT.svg|200px]]
 |}
@@ Line 59: / 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]] || Ethacetin || 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]] || Ethocin || 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-EPT]] || Eprocin || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || OH || H || H || [[File:4-HO-EPT.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]] || 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-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 126: / 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 132: / Line 146: @@
 <references />
 [[Category:Tryptamine| ]]
+{{#set:Featured=true}}