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| [[File:SubstitutedPhenethylamine.png|thumb|right|280px||Substitutive structure of a ''phenethylamine'' molecule.]]
| | {{Page|Substituted phenethylamine}} |
| | | [[Category:Arylethylamine]] |
| '''Substituted phenethylamine''' refers to a class of compounds which typically produce strong psychedelic effects.
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| ==Chemistry==
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| Phenethylamine comprises a ''benzene ring'' attached to a ''mono-amine group'' via an ''ethyl side-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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| Phenethylamines, tabulated by structure (from [[wikipedia:Tryptamine|Wikipedia]])
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| {| class="wikitable sortable mw-collapsible mw-collapsed"
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| ! Short Name
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| ! ''R<sup>N</sup>''
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| ! ''R<sup>α</sup>''
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| ! ''R<sup>β</sup>''
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| ! ''R<sup>2</sup>''
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| ! ''R<sup>3</sup>''
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| ! ''R<sup>4</sup>''
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| ! ''R<sup>5</sup>''
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| ! Full Name
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| ! Biologic activity
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| | [[Tyramine|''meta''-Tyramine]] || || || || || [[Hydroxyl|OH]] || || || 3-hydroxyphenethylamine || [[Trace amine]]
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| | [[Tyramine|''para''-Tyramine]] || || || || || || OH || || 4-hydroxyphenethylamine || [[Trace amine]]
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| | [[Dopamine]] || || || || || OH || OH || || 3,4-dihydroxyphenethylamine || Catecholamine neurotransmitter
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| | [[Epinephrine]] (Adrenaline) || [[methyl group|CH<sub>3</sub>]] || || OH || || OH || OH || || β,3,4-trihydroxy-''N''-[[methyl group|methyl]]<nowiki>phenethylamine</nowiki> || Catecholamine neurotransmitter/Fight or Flight hormone
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| | [[Norepinephrine]] (Noradrenaline) || || || OH || || OH || OH || || β,3,4-trihydroxyphenethylamine || Catecholamine neurotransmitter/Fight or Flight hormone
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| | [[Norfenefrine|''meta''-Octopamine]] || || || OH || || OH || || || β,3-dihydroxyphenethylamine || [[Trace amine]]
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| | [[Octopamine|''para''-Octopamine]] || || || OH || || || OH || || β,4-dihydroxyphenethylamine || [[Trace amine|Trace aminergic]] [[α-adrenoceptor]] agonist
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| | [[Phenylephrine]] || CH<sub>3</sub> || || OH || || OH || || || β,3-dihydroxy-''N''-methylphenethylamin || α-adrenergic agonist; [[decongestant]]
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| | [[6-Hydroxydopamine]] || || || || OH || || OH || OH || 2,4,5-trihydroxyphenethylamine || neurotoxic agent for the [[dopamine]] and [[norepinephrine]] receptors
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| | [[Salbutamol]] || C(CH<sub>3</sub>)<sub>3</sub> || ||OH|| || || OH || CH<sub>2</sub>OH || β,4-dihydroxy-3-hydroxymethyl-''N''-''tert''-butylphenethylamine || Short-action [[Beta2-adrenergic receptor agonist| β<sub>2</sub>-adrenergic agonist]]
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| | [[β-Methylphenethylamine]] || || || CH<sub>3</sub> || || || || || β-methylphenethylamine || Stimulant
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| | [[Amphetamine]] || || CH<sub>3</sub> || || || || || || α-methylphenethylamine || [[Monoamine]] [[releasing agent]]; [[Stimulant]]
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| | [[N-Methylphenethylamine]] || CH<sub>3</sub>|| || || || || || ||''N''-methylphenethylamine || Endogenous amphetamine isomer; [[Trace amine]]
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| | [[Methamphetamine]] || CH<sub>3</sub>|| CH<sub>3</sub> || || || || || || ''N''-methylamphetamine || [[Monoamine]] [[releasing agent]]; [[Stimulant]]; dopaminergic neurotoxin
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| | [[Methylphenidate]] ||colspan=2| -CH<sub>2</sub>-CH<sub>2</sub>-CH<sub>2</sub>-CH<sub>2</sub>- || C(OCH<sub>3</sub>)=O || || || || || ''N'',α-butylene-β-methoxycarbonylphenethylamine || [[Norepinephrine-dopamine reuptake inhibitor| NDRI]]; [[Stimulant]]
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| | [[Ephedrine]] / [[Pseudoephedrine]] || CH<sub>3</sub>|| CH<sub>3</sub> || OH || || || || || ''N''-methyl-β-hydroxyamphetamine || [[Releasing agent]]; [[stimulant]]; [[decongestant]]
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| | [[Cathine]] || || CH<sub>3</sub> || OH || || || || || d-β-hydroxyamphetamine || Somewhat selective [[norepinephrine releasing agent]]
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| | [[Cathinone]] || || CH<sub>3</sub> || =O || || || || || β-ketoamphetamine || Selective norepinephrine and dopamine [[releasing agent]]
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| | [[Methcathinone]] || CH<sub>3</sub> || CH<sub>3</sub> || =O || || || || || ''N''-methylcathinone || Selective norepinephrine and dopamine [[releasing agent]]
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| | [[Mephedrone]] || CH<sub>3</sub> || CH<sub>3</sub> || =O || || || CH<sub>3</sub> || || 4-methylmethcathinone || Stimulant, unknown pharmacodynamics actions
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| | [[Ethcathinone]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || =O || || || || || ''N''-ethylcathinone || Stimulant and Norepinephrine releasing agent
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| | [[Bupropion]] || C(CH<sub>3</sub>)<sub>3</sub>|| CH<sub>3</sub> || =O || || [[chlorine|Cl]] || || || 3-[[chloro]]-''N''-''tert''-butyl-β-ketoamphetamine || NDRI
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| | [[Norfenfluramine]] || || CH<sub>3</sub> || || || [[trifluoromethyl|CF<sub>3</sub>]] || || || 3-[[trifluoromethyl]]-amphetamine || [[Selective serotonin releasing agent|SSRA]]
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| | [[Fenfluramine]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || || || CF<sub>3</sub> || || || 3-trifluoromethyl-''N''-[[ethyl group|ethyl]]-amphetamine || [[Selective serotonin releasing agent|SSRA]]
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| | [[Phentermine]] || || 2CH<sub>3</sub> || || || || || || α,α-dimethylphenethylamine || Stimulant, anorectic
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| | [[5-(2-aminopropyl)benzofuran|5-APB]] || || CH<sub>3</sub> || || ||colspan=2| -CH=CH-O- || || 5-(2-aminopropyl)benzofuran || [[stimulant]], [[entactogen]]
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| | [[6-(2-aminopropyl)benzofuran|6-APB]] || || CH<sub>3</sub> || || ||colspan=2| -O-CH=CH- || || 6-(2-aminopropyl)benzofuran || [[stimulant]], [[entactogen]]
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| | [[3,4-methylenedioxyamphetamine|MDA]] || || CH<sub>3</sub> || || ||colspan=2| -O-CH<sub>2</sub>-O- || || 3,4-[[methylenedioxy]]<nowiki>amphetamine</nowiki> || Stimulant, psychedelic, [[entactogen]]
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| | [[Methylenedioxyethylamphetamine|MDEA]] || CH<sub>2</sub>CH<sub>3</sub>|| CH<sub>3</sub> || || ||colspan=2| -O-CH<sub>2</sub>-O- || || 3,4-methylenedioxy-''N''-ethylamphetamine || [[psychedelic]], [[entactogen]] and [[releasing agent]]
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| | [[MDMA]] || CH<sub>3</sub>|| CH<sub>3</sub> || || ||colspan=2| -O-CH<sub>2</sub>-O- || || 3,4-methylenedioxy-''N''-methylamphetamine || [[psychedelic]], [[entactogen]] and [[releasing agent]]
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| | [[MDMC]] || CH<sub>3</sub>|| CH<sub>3</sub> || =O || ||colspan=2| -O-CH<sub>2</sub>-O- || || 3,4-methylenedioxymethcathinone || [[psychedelic]], [[entactogen]] and [[releasing agent]]
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| | [[Mescaline]] || || || || || [[methoxy|OCH<sub>3</sub>]] || OCH<sub>3</sub> || OCH<sub>3</sub> || 3,4,5-tri[[methoxy]]<nowiki>phenethylamine</nowiki> || Serotonergic [[Psychedelic]]
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| | [[Proscaline]] || || || || || OCH<sub>3</sub>||OCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>|| OCH<sub>3</sub> || 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine|| [[Stimulant]], [[entactogen]] and [[euphoriant]]
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| | [[Metaescaline]] || || || || || [[methoxy|OCH<sub>2</sub>CH<sub>3</sub>]] || OCH<sub>3</sub> || OCH<sub>3</sub> || 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine|| Serotonergic [[Psychedelic]], [[stimulant]], [[entactogen]] and [[euphoriant]]
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| | [[Allylescaline]] || || || || || OCH<sub>3</sub>||OCH<sub>2</sub>CH<sub>1</sub>CH<sub>2</sub>|| OCH<sub>3</sub> || 4-Allyloxy-3,5-dimethyloxyphenylethylamine|| [[Stimulant]], [[entactogen]] and [[euphoriant]]
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| | [[Asymbescaline]] || || || || || OCH<sub>2</sub>CH<sub>3</sub>||OCH<sub>2</sub>CH<sub>3</sub>|| OCH<sub>3</sub> || 3,4-Diethoxy-5-methoxyphenethylamine|| Psychedelic and [[euphoriant]]
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| | [[2,5-dimethoxy-4-methylamphetamine|DOM]] || || CH<sub>3</sub> || || OCH<sub>3</sub> || || CH<sub>3</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-methylamphetamine || [[psychedelic]]
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| | [[2,5-dimethoxy-4-bromoamphetamine|DOB]] || || CH<sub>3</sub> || || OCH<sub>3</sub> || || [[bromine|Br]] || OCH<sub>3</sub> || 2,5-dimethoxy-4-[[bromine|bromo]]<nowiki>amphetamine</nowiki> || Psychedelic
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| | [[2,5-dimethoxy-4-iodoamphetamine|DOI]] || || CH<sub>3</sub> || || OCH<sub>3</sub> || || [[iodine|I]] || OCH<sub>3</sub> || 2,5-dimethoxy-4-[[Iodine|iodo]]<nowiki>amphetamine</nowiki> || [[Psychedelic drug|Psychedelic]]
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| | [[2,5-dimethoxy-4-nitroamphetamine|DON]] || || CH<sub>3</sub> || || OCH<sub>3</sub> || || [[nitro compound|NO<sub>2</sub>]] || OCH<sub>3</sub> || 2,5-dimethoxy-4-[[Nitro compound|nitro]]<nowiki>amphetamine</nowiki>|| [[Stimulant]]
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| | [[2,5-dimethoxy-4-chloroamphetamine|DOC]] || || CH<sub>3</sub> || || OCH<sub>3</sub> || || [[Chlorine|Cl]] || OCH<sub>3</sub> || 2,5-dimethoxy-4-[[chloro]]<nowiki>amphetamine</nowiki>|| [[Psychedelic drug|Psychedelic]]
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| | [[2C-B]] || || || || OCH<sub>3</sub> || || Br || OCH<sub>3</sub> || 2,5-dimethoxy-4-bromophenethylamine|| [[Psychedelic drug|Psychedelic]], [[stimulant]], [[entactogen]] and [[euphoriant]]
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| | [[βk-2C-B]] || || || =O || OCH<sub>3</sub> || || Br || OCH<sub>3</sub> || 2,5-dimethoxy-4-bromo-β-ketophenethylamine|| [[Psychedelic drug|Psychedelic]], [[stimulant]], [[entactogen]] and [[euphoriant]]
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| | [[2C-C]] || || || || OCH<sub>3</sub> || || Cl || OCH<sub>3</sub> || 2,5-dimethoxy-4-chlorophenethylamine|| [[Psychedelic drug|Psychedelic]]
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| | [[2C-I]] || || || || OCH<sub>3</sub> || || I || OCH<sub>3</sub> || 2,5-dimethoxy-4-iodophenethylamine|| [[Psychedelic drug|Psychedelic]], [[stimulant]]
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| | [[2C-D]] || || || || OCH<sub>3</sub> || || CH<sub>3</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-methylphenethylamine || [[Psychedelic drug|Psychedelic]], [[stimulant]]
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| | [[2C-E]] || || || || OCH<sub>3</sub> || || CH<sub>2</sub>-CH<sub>3</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-ethylphenethylamine|| [[Psychedelic drug|Psychedelic]]
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| | [[2C-P]] || || || || OCH<sub>3</sub> || || CH<sub>2</sub>-CH<sub>3</sub>-CH<sub>3</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-propylphenethylamine || [[Entactogen]], [[euphoriant]] and Psychedelic
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| | [[2C-F]] || || || || OCH<sub>3</sub> || || [[fluorine|F]] || OCH<sub>3</sub> || 2,5-dimethoxy-4-[[fluoro]]<nowiki>phenethylamine</nowiki> || None
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| | [[2C-N]] || || || || OCH<sub>3</sub> || || NO<sub>2</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-nitrophenethylamine || [[euphoriant]]
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| | [[2C-T-2]] || || || || OCH<sub>3</sub> || || [[Thio-|S]]-CH<sub>2</sub>CH<sub>3</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-ethyl[[Thio-|thio]]-phenethylamine || Psychedelic
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| | [[2C-T-4]] || || || || OCH<sub>3</sub> || || S-[[isopropyl|CH(CH<sub>3</sub>)<sub>2</sub>]] || OCH<sub>3</sub> || 2,5-dimethoxy-4-[[isopropyl]]<nowiki>thio</nowiki>-phenethylamine || Psychedelic
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| | [[2C-T-7]] || || || || OCH<sub>3</sub> || || S-CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-propylthio-phenethylamine || Psychedelic
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| | [[2C-T-8]] || || || || OCH<sub>3</sub> || || S-CH<sub>2</sub>-[[cyclopropyl|C<sub>3</sub>H<sub>5</sub>]] || OCH<sub>3</sub> || 2,5-dimethoxy-4-[[cyclopropyl]]<nowiki>methylthio</nowiki>-phenethylamine || Psychedelic
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| | [[2C-T-9]] || || || || OCH<sub>3</sub> || || S-C(CH<sub>3</sub>)<sub>3</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-''tert''-butylthio-phenethylamine || Psychedelic
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| | [[2C-T-21]] || || || || OCH<sub>3</sub> || || S-CH<sub>2</sub>-CH<sub>2</sub>-F || OCH<sub>3</sub> || 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine || Psychedelic and [[euphoriant]]
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| | [[25B-NBOMe]] ||CH<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>-OCH<sub>3</sub> || || || OCH<sub>3</sub> || || Br || OCH<sub>3</sub> || 2-(4-bromo-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic
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| | [[25C-NBOMe]] ||CH<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>-OCH<sub>3</sub> || || || OCH<sub>3</sub> || || Cl || OCH<sub>3</sub> || 2-(4-chloro-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic
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| | [[25I-NBOMe]] ||CH<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>-OCH<sub>3</sub> || || || OCH<sub>3</sub> || || I || OCH<sub>3</sub> || 2-(4-iodo-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic
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| | [[25D-NBOMe]] ||CH<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>-OCH<sub>3</sub> || || || OCH<sub>3</sub> || || CH<sub>2</sub> || OCH<sub>3</sub> || 2-(4-methyl-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic
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| | [[25E-NBOMe]] ||CH<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>-OCH<sub>3</sub> || || || OCH<sub>3</sub> || || CH<sub>2</sub>-CH<sub>3</sub> || OCH<sub>3</sub> || 2-(4-ethyl-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic
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| | [[25P-NBOMe]] ||CH<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>-OCH<sub>3</sub> || || || OCH<sub>3</sub> || || CH<sub>2</sub>-CH<sub>3</sub>-CH<sub>3</sub> || OCH<sub>3</sub> || 2-(4-propyl-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic
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| | [[25F-NBOMe]] ||CH<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>-OCH<sub>3</sub> || || || OCH<sub>3</sub> || || F || OCH<sub>3</sub> || 2-(4-fluoro-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic
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| | [[Mescaline-NBOMe]] ||CH<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>-OCH<sub>3</sub> || || || || [[methoxy|OCH<sub>3</sub>]] || OCH<sub>3</sub> || OCH<sub>3</sub> || ''N''-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanamine || Psychedelic
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| |[[25I-NBOH]]|| CH<sub>2</sub>–C<sub>6</sub>H<sub>4</sub>–OH || || || OCH<sub>3</sub> || || I || OCH<sub>3</sub> || ''N''-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine || Psychedelic
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| |[[25C-NBOH]]|| CH<sub>2</sub>–C<sub>6</sub>H<sub>4</sub>–OH || || || OCH<sub>3</sub> || || Cl || OCH<sub>3</sub> || ''N''-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine || Psychedelic
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| |[[25B-NBOH]]|| CH<sub>2</sub>–C<sub>6</sub>H<sub>4</sub>–OH || || || OCH<sub>3</sub> || || Br || OCH<sub>3</sub> || ''N''-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine || Psychedelic
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| |[[25I-NBF]]|| CH<sub>2</sub>–C<sub>6</sub>H<sub>4</sub>–F || || || OCH<sub>3</sub> || || I || OCH<sub>3</sub> || ''N''-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine || Psychedelic
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| |-class="sortbottom"
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| ! Short Name
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| ! ''R<sup>N</sup>''
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| ! ''R<sup>α</sup>''
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| ! ''R<sup>β</sup>''
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| ! ''R<sup>2</sup>''
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| ! ''R<sup>3</sup>''
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| ! ''R<sup>4</sup>''
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| ! ''R<sup>5</sup>''
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| ! Full Name
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| |}
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| ==Pharmacology==
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| Phenethylamines 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 phenethylamine, such as:
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| *[[Adrenaline]]
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| *[[Dopamine]]
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| *[[Noradrenaline]]
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| [[Category:Psychedelic]] | | [[Category:Psychedelic]] |
