Substituted tryptamines: Difference between revisions

>Lluxull
Added a sentence about Lysergamides being technically tryptamines
>David Hedlund
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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]].   
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==
==Chemistry==
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==List of substituted tryptamines==
==List of substituted tryptamines==
''This table does not include the following groups of substituted tryptamines:''
* [[Lysergamides]]
====Ring-unsubstituted tryptamines====
====Ring-unsubstituted tryptamines====
''Sometimes referred to as "unsubstituted tryptamines" or "base tryptamines"''
''Sometimes referred to as "unsubstituted tryptamines" or "base tryptamines"''
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! 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>2</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>6</sub>'''
! scope="col" style="width: 50px;" |'''R<sub>α</sub>'''
! scope="col" style="width: 50px;" |'''R<sub>α</sub>'''
! scope="col" style="width: 50px;" |'''R<sub>β</sub>'''
! scope="col" |'''Structure'''
! 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]]
|}
|}


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<references />
<references />
[[Category:Tryptamine| ]]
[[Category:Tryptamine| ]]
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