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| [[File:SubstitutedTryptamine.png|thumb|right|294px|Substitutive structure of a ''tryptamine'' molecule.]]
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| '''Tryptamine''' is a mono-amine alkaloid found in animals, plants and fungi.
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| '''Substituted tryptamine''' refers to a class of compounds which typically produce strong psychedelic effects.
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| ==Chemistry==
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| Tryptamine comprises an ''indole ring'' attached to a ''mono-amine chain''. Hydrogen atoms around the structure can be substituted for other functional groups to produce drugs of varying potency, efficacy and half-life.
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| {| class="wikitable sortable mw-collapsible mw-collapsed" width="100%"
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| |+ Tryptamines, tabulated by structure
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| |-
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| ! Short Name
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| ! Origin
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| ! R<sup>α</sup>
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| ! R<sup>4</sup>
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| ! R<sup>5</sup>
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| ! R<sup>N1</sup>
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| ! R<sup>N2</sup>
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| ! Full Name
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| |-
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| | Tryptamine||Natural|| H || H || H || H || H || 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine
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| |-
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| | [[Bufotenin]]||Natural|| H || H || OH || CH<sub>3</sub> || CH<sub>3</sub> || 5-hydroxy-''N,N''-dimethyltryptamine
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| |-
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| | [[N-Methylserotonin|''N''<sub>ω</sub>-methylserotonin]] (norbufotenin)||Natural|| H || H || OH || CH<sub>3</sub> || H || 5-hydroxy-''N''-methyltryptamine
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| |-
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| | [[Serotonin]]||Natural|| H || H || OH ||H ||H || 5-hydroxytryptamine
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| |-
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| | [[Dimethyltryptamine|DMT]]||Natural|| H || H || H || [[Methyl|CH<sub>3</sub>]] ||CH<sub>3</sub> || ''N,N''-dimethyltryptamine
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| |-
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| | [[Melatonin]]||Natural|| H || H || [[Methoxy|OCH<sub>3</sub>]] || [[acetyl|O=C-CH<sub>3</sub>]] ||H || 5-methoxy-''N''-acetyltryptamine
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| |-
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| | [[5-Bromo-DMT]]||Natural|| H || H || Br || CH<sub>3</sub> || CH<sub>3</sub> || 5-bromo-''N,N''-dimethyltryptamine
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| |-
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| | [[5-MeO-DMT]]||Natural|| H || H || OCH<sub>3</sub> || CH<sub>3</sub> || CH<sub>3</sub> || 5-methoxy-''N,N''-dimethyltryptamine
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| |-
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| | [[5-MeO-NMT]]||Natural|| H || H || OCH<sub>3</sub> || CH<sub>3</sub> || H || 5-methoxy-''N''-methyltryptamine
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| |-
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| | [[N-Methyltryptamine|NMT]]||Natural|| H || H || H || H ||CH<sub>3</sub> || ''N''-methyltryptamine
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| |-
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| | [[Norbaeocystin]]||Natural|| H || OPO<sub>3</sub>H<sub>2</sub> || H || H || H || 4-phosphoryloxy-tryptamine
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| |-
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| | [[Baeocystin]]||Natural|| H || OPO<sub>3</sub>H<sub>2</sub> || H || CH<sub>3</sub> || H || 4-phosphoryloxy-''N''-methyl-tryptamine
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| |-
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| | [[Psilocybin]]||Natural|| H || [[Phosphate|PO<sub>4</sub>]] || H || CH<sub>3</sub> || CH<sub>3</sub> || 4-phosphoryloxy-''N,N''-dimethyltryptamine
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| |-
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| | [[Psilocin]]||Natural|| H || [[Hydroxyl|OH]] || H || CH<sub>3</sub> || CH<sub>3</sub> || 4-hydroxy-''N,N''-dimethyltryptamine
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| |-
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| | [[Tryptophan]]||Natural|| [[Carboxyl|COOH]] || H || H || H || H || α-carboxyltryptamine
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| |-
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| | [[Alpha-ethyltryptamine|αET]]
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| |Artificial
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| | [[Ethyl group|CH<sub>2</sub>CH<sub>3</sub>]]
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| | H
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| | H
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| | H
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| | H
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| | α-ethyltryptamine
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| |-
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| | [[Alphamethyltryptamine|αMT]]
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| |Artificial
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| | [[Methyl|CH<sub>3</sub>]]
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| | H
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| | H
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| | H
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| | H
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| | α-methyltryptamine
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| |-
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| | [[Diallyltryptamine|DALT]]
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| |Artificial
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| | H
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| | H
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| | H
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| | [[Allyl|H<sub>2</sub>C=CH-CH<sub>2</sub>]]
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| | H<sub>2</sub>C=CH-CH<sub>2</sub>
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| | ''N,N''-diallyltryptamine
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| |-
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| | [[Diethyltryptamine|DET]]
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| |Artificial
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| | H
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| | H
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| | H
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| | CH<sub>2</sub>CH<sub>3</sub>
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| | CH<sub>2</sub>CH<sub>3</sub>
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| | ''N,N''-diethyltryptamine
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| |-
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| | [[Diisopropyltryptamine|DiPT]]
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| |Artificial
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| | H
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| | H
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| | H
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| | [[Isopropyl|CH(CH<sub>3</sub>)<sub>2</sub>]]
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| | CH(CH<sub>3</sub>)<sub>2</sub>
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| | ''N,N''-diisopropyltryptamine
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| |-
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| | [[Dipropyltryptamine|DPT]]
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| |Artificial
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| | H
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| | H
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| | H
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| | [[Propyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]]
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| | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>
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| | ''N,N''-dipropyltryptamine
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| |-
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| | [[5-MeO-αMT]]
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| |Artificial
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| | CH<sub>3</sub>
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| | H
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| | [[Methoxy|OCH<sub>3</sub>]]
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| | H
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| | H
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| | 5-methoxy-α-methyltryptamine
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| |-
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| | [[5-MeO-DALT]]
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| |Artificial
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| | H
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| | H
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| | [[Methoxy|OCH<sub>3</sub>]]
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| | [[Allyl|H<sub>2</sub>C=CH-CH<sub>2</sub>]]
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| | H<sub>2</sub>C=CH-CH<sub>2</sub>
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| | 5-methoxy-''N,N''-diallyltryptamine
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| |-
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| | [[4-HO-DET]]
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| |Artificial
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| | H
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| | OH
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| | H
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| | CH<sub>2</sub>CH<sub>3</sub>
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| | CH<sub>2</sub>CH<sub>3</sub>
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| | 4-hydroxy-''N,N''-diethyltryptamine
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| |-
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| | [[4-AcO-DMT]]
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| |Artificial
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| | H
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| | OCOCH<sub>3</sub>
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| | H
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| | CH<sub>3</sub>
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| | CH<sub>3</sub>
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| | 4-acetoxy-''N,N''-dimethyltryptamine
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| |-
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| | [[4-HO-MET]]
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| |Artificial
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| | H
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| | OH
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| | H
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| | CH<sub>3</sub>
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| | CH<sub>2</sub>CH<sub>3</sub>
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| | 4-hydroxy-N-methyl-N-ethyltryptamine
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| |-
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| | [[4-HO-DIPT]]
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| |Artificial
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| | H
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| | OH
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| | H
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| | CH(CH<sub>3</sub>)<sub>2</sub>
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| | CH(CH<sub>3</sub>)<sub>2</sub>
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| | 4-hydroxy-''N,N''-diisopropyltryptamine
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| |-
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| | [[5-MeO-DIPT]]
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| |Artificial
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| | H
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| | H
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| | OCH<sub>3</sub>
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| | CH(CH<sub>3</sub>)<sub>2</sub>
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| | CH(CH<sub>3</sub>)<sub>2</sub>
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| | 5-methoxy-''N,N''-diisopropyltryptamine
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| |-
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| | [[4-HO-MiPT]]
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| |Artificial
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| | H
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| | OH
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| | H
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| | CH(CH<sub>3</sub>)<sub>2</sub>
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| | CH<sub>3</sub>
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| | 4-hydroxy-''N''-isopropyl-''N''-methyltryptamine
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| |-
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| | [[Sumatriptan]]
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| |Artificial
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| | H
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| | H
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| | CH<sub>2</sub>SO<sub>2</sub>NHCH<sub>3</sub>
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| | CH<sub>3</sub>
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| | CH<sub>3</sub>
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| | 5-(methylaminosulfonylmethylene)-''N,N''-dimethyltryptamine
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| |-
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| | [[Zolmitriptan]]
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| |Artificial
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| | H
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| | H
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| | -(CHNHC=OOCH<sub>2</sub>)
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| | CH<sub>3</sub>
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| | CH<sub>3</sub>
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| | 5-( 4-(''S'')-1,3-oxazolidin-2-one)-''N,N''-dimethyltryptamine
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| |-
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| |-class="sortbottom"
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| ! Short Name
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| ! Origin
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| ! R<sup>α</sup>
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| ! R<sup>4</sup>
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| ! R<sup>5</sup>
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| ! R<sup>N1</sup>
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| ! R<sup>N2</sup>
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| ! Full Name
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| |}
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| ==Pharmacology==
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| Tryptamines are believed to produce their psychedelic effect primarily by partial agonism of [[Serotonin#The 5-HT System|5-HT<sub>2A</sub> receptors]].
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| Several [[neurotransmitter]]s are derived from tryptamine, such as:
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| *[[Serotonin]]
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| *[[Melatonin]]
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| ==References==
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| *[[wikipedia:Tryptamine|Tryptamine (Wikipedia)]]
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| [[Category:Psychedelic]] | | [[Category:Psychedelic]] |
