Substituted tryptamines: Difference between revisions

Line 1:

~~#REDIRECT~~ [[Tryptamine]]

[[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.

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>

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]].

An investigation of dozens of psychoactive tryptamine compounds was published by Ann and [[Alexander Shulgin]] under the name [[TiHKAL]] 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.

==List of substituted tryptamines==

====Ring unsubstituted tryptamines====

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

{| class="wikitable"

|-

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

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

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

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

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

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

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

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

| [[AMT]] || || H || H || H || H || CH3 || [[File:αMT.svg|200px]]

|}

====Ring substituted tryptamines====

{| class="wikitable"

|-

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

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

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

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

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

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

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

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

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

|-

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

|}

==See also==

*[[Tryptamine]]

*[[Responsible use]]

*[[Lysergamide]]

*[[TiHKAL]]

*[[Entheogen]]

*[[Phenethylamine]]

==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)]

==References==

[[Category:Tryptamine]]

@@ Line 1: / Line 1: @@
-#REDIRECT [[Tryptamine]]
+[[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.
+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>
+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]].
+An investigation of dozens of psychoactive tryptamine compounds was published by Ann and [[Alexander Shulgin]] under the name [[TiHKAL]] 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.
+==List of substituted tryptamines==
+====Ring unsubstituted tryptamines====
+''Sometimes referred to as "base tryptamines"''.
+{| class="wikitable"
+|-
+! scope="col" | '''Compound'''
+! scope="col" | '''Common name'''
+! scope="col" style="width: 50px;" | '''R<sub>N1</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>N2</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>4</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>5</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>α</sub>'''
+! scope="col" | '''Structure'''
+|-
+| 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]]
+|-
+| [[MET]] || || 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]]
+|-
+| [[MPT]] || || 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]]
+|-
+| [[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]]
+|-
+| [[DiPT]] || || 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]]
+|-
+| [[AMT]] || || H || H || H || H || CH<sub>3</sub> || [[File:αMT.svg|200px]]
+|}
+====Ring substituted tryptamines====
+{| class="wikitable"
+|-
+! scope="col" | '''Compound'''
+! scope="col" | '''Common name'''
+! scope="col" style="width: 50px;" | '''R<sub>N1</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>N2</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>4</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>5</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>α</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-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> || OC(O)CH<sub>3</sub> || 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-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]] || 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-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> || 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> || OH || 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-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> || OP(OH)<sub>2</sub>=O || H || H || [[File:Psilocybin.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 || OH || 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-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]] || || 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]] || || 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 || 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 || 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 || [[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 || OH || CO<sub>2</sub>H || [[File:5-HTP.svg|200px]]
+|}
+==See also==
+*[[Tryptamine]]
+*[[Responsible use]]
+*[[Lysergamide]]
+*[[TiHKAL]]
+*[[Entheogen]]
+*[[Phenethylamine]]
+==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)]
+==References==
+<references />
+[[Category:Tryptamine]]