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==

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"

|-

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! 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]]

|-

|[[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]]

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

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

|-

|[[4-AcO-~~MET~~]]||~~Metacetin~~||CH2CH3~~||CH~~3||OC(O)CH3||H||H||[[File:4-AcO-~~MET~~.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~~-DET]]||~~Ethacetin~~||CH2CH3||CH2CH3||~~OC(O)CH3~~||H||H||[[File:4-~~AcO~~-DET.svg|200px]]

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

|-

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

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

|-

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

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

|-

|[[4-HO-~~DPT~~]]||~~Procin~~||~~CH2~~CH2CH3||~~CH2CH2~~CH3||OH||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-~~MET~~]]||~~Metocin~~||CH2CH3||CH3||OH||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-~~MPT~~]]||~~Meprocin~~||~~CH2CH2~~CH3||CH3||OH||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-~~DMT~~]]||~~Psilocin~~||CH3||CH3||OH||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-HO-~~MiPT~~]]||~~Miprocin~~||CH3||~~CH(~~CH3)2||OH||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]]

|-

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

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

|-

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

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

|-

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

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

|-

|[[5-MeO-~~DMT~~]]|| ||CH3||CH3||H||OCH3||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-~~DET~~]]|| ||CH2CH3||CH2CH3||H||OCH3||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-~~DPT~~]]|| ||CH2CH2~~CH3~~||CH2CH2~~CH3~~||H||OCH3||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-~~DALT~~]]|| ||CH2~~CH=CH~~2||CH2~~CH=CH~~2||H||OCH3||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-~~DiPT~~]]||~~Foxy~~||~~CH(~~CH3~~)2~~||CH(CH3)2||H||OCH3||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]]

|-

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

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

|-

|[[~~Ibogaine~~]]|| ||~~CH2CH2(CH2-)CH2-~~||~~CH2(CH-CH3)CH--~~||H||~~OCH~~3||H||[[File:~~Ibogaine~~.svg|~~201px~~]]

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

|-

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

|}

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==References==

[[Category:Tryptamine|*]]

[[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"
 |-
@@ Line 33: / Line 35: @@
 ! 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]]
+|-
+|[[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]]
@@ Line 61: / Line 65: @@
 ! 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>||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>||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-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-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-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-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-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-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-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-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-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-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-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-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-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-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-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-DMT]]||Psilocin||CH<sub>3</sub>||CH<sub>3</sub>||H||OH||H||H||H||H||[[File:Psilocin.svg|200px]]
 |-
-|[[4-HO-DMT]]||Psilocin||CH<sub>3</sub>||CH<sub>3</sub>||OH||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-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-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]]
 |-
-|[[4-PO-DMT]]||Psilocybin||CH<sub>3</sub>||CH<sub>3</sub>||OP(OH)<sub>2</sub>=O||H||H||[[File:Psilocybin.svg|200px]]
+|[[Serotonin]]|| ||H||H||H||H||OH||H||H||H||[[File:Serotonin.svg|200px]]
 |-
-|[[Serotonin]]|| ||H||H||H||OH||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-HO-DMT]]||Bufotenin||CH<sub>3</sub>||CH<sub>3</sub>||H||OH||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-DMT]]|| ||CH<sub>3</sub>||CH<sub>3</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DMT.svg|200px]]
+|[[5-MeO-DET]]|| ||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||H||OCH<sub>3</sub>||H||H||H||[[File:5-MeO-DET.svg|200px]]
 |-
-|[[5-MeO-DET]]|| ||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||OCH<sub>3</sub>||H||[[File:5-MeO-DET.svg|200px]]
+|[[5-MeO-DPT]]||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-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-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-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-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-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-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]]
 |-
-|[[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]]
+|[[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]]
 |-
-|[[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-HTP]]|| ||H||H||H||H||OH||H||CO<sub>2</sub>H||H||[[File:5-HTP.svg|200px]]
 |-
-|[[Melatonin]]|| ||H||COCH<sub>3</sub>||H||OCH<sub>3</sub>||H||[[File:Melatonin.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]]
 |}
@@ Line 129: / Line 145: @@
 ==References==
 <references />
-[[Category:Tryptamine|*]]
+[[Category:Tryptamine| ]]
+{{#set:Featured=true}}