Category:Phenethylamine: Difference between revisions

Line 1:

[[File:SubstitutedPhenethylamine.png|thumb|right|280px||Substitutive structure of a ''phenethylamine'' molecule.]]

'''Substituted phenethylamine''' refers to a class of compounds which typically produce strong psychedelic effects.

==Chemistry==

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.

Phenethylamines, tabulated by structure (from [[wikipedia:Tryptamine|Wikipedia]])

{| class="wikitable sortable mw-collapsible collapsed"

|-

! Short Name

! ''RN''

! ''Rα''

! ''Rβ''

! ''R2''

! ''R3''

! ''R4''

! ''R5''

! Full Name

! Biologic activity

|-

| [[Tyramine|''meta''-Tyramine]] || || || || || [[Hydroxyl|OH]] || || || 3-hydroxyphenethylamine || [[Trace amine]]

|-

| [[Tyramine|''para''-Tyramine]] || || || || || || OH || || 4-hydroxyphenethylamine || [[Trace amine]]

|-

| [[Dopamine]] || || || || || OH || OH || || 3,4-dihydroxyphenethylamine || Catecholamine neurotransmitter

|-

| [[Epinephrine]] (Adrenaline) || [[methyl group|CH3]] || || OH || || OH || OH || || β,3,4-trihydroxy-''N''-[[methyl group|methyl]]<nowiki>phenethylamine</nowiki> || Catecholamine neurotransmitter/Fight or Flight hormone

|-

| [[Norepinephrine]] (Noradrenaline) || || || OH || || OH || OH || || β,3,4-trihydroxyphenethylamine || Catecholamine neurotransmitter/Fight or Flight hormone

|-

| [[Norfenefrine|''meta''-Octopamine]] || || || OH || || OH || || || β,3-dihydroxyphenethylamine || [[Trace amine]]

|-

| [[Octopamine|''para''-Octopamine]] || || || OH || || || OH || || β,4-dihydroxyphenethylamine || [[Trace amine|Trace aminergic]] [[α-adrenoceptor]] agonist

|-

| [[Phenylephrine]] || CH3 || || OH || || OH || || || β,3-dihydroxy-''N''-methylphenethylamin || α-adrenergic agonist; [[decongestant]]

|-

| [[6-Hydroxydopamine]] || || || || OH || || OH || OH || 2,4,5-trihydroxyphenethylamine || neurotoxic agent for the [[dopamine]] and [[norepinephrine]] receptors

|-

| [[Salbutamol]] || C(CH3)3 || ||OH|| || || OH || CH2OH || β,4-dihydroxy-3-hydroxymethyl-''N''-''tert''-butylphenethylamine || Short-action [[Beta2-adrenergic receptor agonist| β2-adrenergic agonist]]

|-

| [[β-Methylphenethylamine]] || || || CH3 || || || || || β-methylphenethylamine || Stimulant

|-

| [[Amphetamine]] || || CH3 || || || || || || α-methylphenethylamine || [[Monoamine]] [[releasing agent]]; [[Stimulant]]

|-

| [[N-Methylphenethylamine]] || CH3|| || || || || || ||''N''-methylphenethylamine || Endogenous amphetamine isomer; [[Trace amine]]

|-

| [[Methamphetamine]] || CH3|| CH3 || || || || || || ''N''-methylamphetamine || [[Monoamine]] [[releasing agent]]; [[Stimulant]]; dopaminergic neurotoxin

|-

| [[Methylphenidate]] ||colspan=2| -CH2-CH2-CH2-CH2- || C(OCH3)=O || || || || || ''N'',α-butylene-β-methoxycarbonylphenethylamine || [[Norepinephrine-dopamine reuptake inhibitor| NDRI]]; [[Stimulant]]

|-

| [[Ephedrine]] / [[Pseudoephedrine]] || CH3|| CH3 || OH || || || || || ''N''-methyl-β-hydroxyamphetamine || [[Releasing agent]]; [[stimulant]]; [[decongestant]]

|-

| [[Cathine]] || || CH3 || OH || || || || || d-β-hydroxyamphetamine || Somewhat selective [[norepinephrine releasing agent]]

|-

| [[Cathinone]] || || CH3 || =O || || || || || β-ketoamphetamine || Selective norepinephrine and dopamine [[releasing agent]]

|-

| [[Methcathinone]] || CH3 || CH3 || =O || || || || || ''N''-methylcathinone || Selective norepinephrine and dopamine [[releasing agent]]

|-

| [[Mephedrone]] || CH3 || CH3 || =O || || || CH3 || || 4-methylmethcathinone || Stimulant, unknown pharmacodynamics actions

|-

| [[Ethcathinone]] || CH2CH3 || CH3 || =O || || || || || ''N''-ethylcathinone || Stimulant and Norepinephrine releasing agent

|-

| [[Bupropion]] || C(CH3)3|| CH3 || =O || || [[chlorine|Cl]] || || || 3-[[chloro]]-''N''-''tert''-butyl-β-ketoamphetamine || NDRI

|-

| [[Norfenfluramine]] || || CH3 || || || [[trifluoromethyl|CF3]] || || || 3-[[trifluoromethyl]]-amphetamine || [[Selective serotonin releasing agent|SSRA]]

|-

| [[Fenfluramine]] || CH2CH3 || CH3 || || || CF3 || || || 3-trifluoromethyl-''N''-[[ethyl group|ethyl]]-amphetamine || [[Selective serotonin releasing agent|SSRA]]

|-

| [[Phentermine]] || || 2CH3 || || || || || || α,α-dimethylphenethylamine || Stimulant, anorectic

|-

| [[5-(2-aminopropyl)benzofuran|5-APB]] || || CH3 || || ||colspan=2| -CH=CH-O- || || 5-(2-aminopropyl)benzofuran || [[stimulant]], [[entactogen]]

|-

| [[6-(2-aminopropyl)benzofuran|6-APB]] || || CH3 || || ||colspan=2| -O-CH=CH- || || 6-(2-aminopropyl)benzofuran || [[stimulant]], [[entactogen]]

|-

| [[3,4-methylenedioxyamphetamine|MDA]] || || CH3 || || ||colspan=2| -O-CH2-O- || || 3,4-[[methylenedioxy]]<nowiki>amphetamine</nowiki> || Stimulant, psychedelic, [[entactogen]]

|-

| [[Methylenedioxyethylamphetamine|MDEA]] || CH2CH3|| CH3 || || ||colspan=2| -O-CH2-O- || || 3,4-methylenedioxy-''N''-ethylamphetamine || [[psychedelic]], [[entactogen]] and [[releasing agent]]

|-

| [[MDMA]] || CH3|| CH3 || || ||colspan=2| -O-CH2-O- || || 3,4-methylenedioxy-''N''-methylamphetamine || [[psychedelic]], [[entactogen]] and [[releasing agent]]

|-

| [[MDMC]] || CH3|| CH3 || =O || ||colspan=2| -O-CH2-O- || || 3,4-methylenedioxymethcathinone || [[psychedelic]], [[entactogen]] and [[releasing agent]]

|-

| [[Mescaline]] || || || || || [[methoxy|OCH3]] || OCH3 || OCH3 || 3,4,5-tri[[methoxy]]<nowiki>phenethylamine</nowiki> || Serotonergic [[Psychedelic]]

|-

| [[Proscaline]] || || || || || OCH3||OCH2CH2CH3|| OCH3 || 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine|| [[Stimulant]], [[entactogen]] and [[euphoriant]]

|-

| [[Metaescaline]] || || || || || [[methoxy|OCH2CH3]] || OCH3 || OCH3 || 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine|| Serotonergic [[Psychedelic]], [[stimulant]], [[entactogen]] and [[euphoriant]]

|-

| [[Allylescaline]] || || || || || OCH3||OCH2CH1CH2|| OCH3 || 4-Allyloxy-3,5-dimethyloxyphenylethylamine|| [[Stimulant]], [[entactogen]] and [[euphoriant]]

|-

| [[Asymbescaline]] || || || || || OCH2CH3||OCH2CH3|| OCH3 || 3,4-Diethoxy-5-methoxyphenethylamine|| Psychedelic and [[euphoriant]]

|-

| [[2,5-dimethoxy-4-methylamphetamine|DOM]] || || CH3 || || OCH3 || || CH3 || OCH3 || 2,5-dimethoxy-4-methylamphetamine || [[psychedelic]]

|-

| [[2,5-dimethoxy-4-bromoamphetamine|DOB]] || || CH3 || || OCH3 || || [[bromine|Br]] || OCH3 || 2,5-dimethoxy-4-[[bromine|bromo]]<nowiki>amphetamine</nowiki> || Psychedelic

|-

| [[2,5-dimethoxy-4-iodoamphetamine|DOI]] || || CH3 || || OCH3 || || [[iodine|I]] || OCH3 || 2,5-dimethoxy-4-[[Iodine|iodo]]<nowiki>amphetamine</nowiki> || [[Psychedelic drug|Psychedelic]]

|-

| [[2,5-dimethoxy-4-nitroamphetamine|DON]] || || CH3 || || OCH3 || || [[nitro compound|NO2]] || OCH3 || 2,5-dimethoxy-4-[[Nitro compound|nitro]]<nowiki>amphetamine</nowiki>|| [[Stimulant]]

|-

| [[2,5-dimethoxy-4-chloroamphetamine|DOC]] || || CH3 || || OCH3 || || [[Chlorine|Cl]] || OCH3 || 2,5-dimethoxy-4-[[chloro]]<nowiki>amphetamine</nowiki>|| [[Psychedelic drug|Psychedelic]]

|-

| [[2C-B]] || || || || OCH3 || || Br || OCH3 || 2,5-dimethoxy-4-bromophenethylamine|| [[Psychedelic drug|Psychedelic]], [[stimulant]], [[entactogen]] and [[euphoriant]]

|-

| [[βk-2C-B]] || || || =O || OCH3 || || Br || OCH3 || 2,5-dimethoxy-4-bromo-β-ketophenethylamine|| [[Psychedelic drug|Psychedelic]], [[stimulant]], [[entactogen]] and [[euphoriant]]

|-

| [[2C-C]] || || || || OCH3 || || Cl || OCH3 || 2,5-dimethoxy-4-chlorophenethylamine|| [[Psychedelic drug|Psychedelic]]

|-

| [[2C-I]] || || || || OCH3 || || I || OCH3 || 2,5-dimethoxy-4-iodophenethylamine|| [[Psychedelic drug|Psychedelic]], [[stimulant]]

|-

| [[2C-D]] || || || || OCH3 || || CH3 || OCH3 || 2,5-dimethoxy-4-methylphenethylamine || [[Psychedelic drug|Psychedelic]], [[stimulant]]

|-

| [[2C-E]] || || || || OCH3 || || CH2-CH3 || OCH3 || 2,5-dimethoxy-4-ethylphenethylamine|| [[Psychedelic drug|Psychedelic]]

|-

| [[2C-P]] || || || || OCH3 || || CH2-CH3-CH3 || OCH3 || 2,5-dimethoxy-4-propylphenethylamine || [[Entactogen]], [[euphoriant]] and Psychedelic

|-

| [[2C-F]] || || || || OCH3 || || [[fluorine|F]] || OCH3 || 2,5-dimethoxy-4-[[fluoro]]<nowiki>phenethylamine</nowiki> || None

|-

| [[2C-N]] || || || || OCH3 || || NO2 || OCH3 || 2,5-dimethoxy-4-nitrophenethylamine || [[euphoriant]]

|-

| [[2C-T-2]] || || || || OCH3 || || [[Thio-|S]]-CH2CH3 || OCH3 || 2,5-dimethoxy-4-ethyl[[Thio-|thio]]-phenethylamine || Psychedelic

|-

| [[2C-T-4]] || || || || OCH3 || || S-[[isopropyl|CH(CH3)2]] || OCH3 || 2,5-dimethoxy-4-[[isopropyl]]<nowiki>thio</nowiki>-phenethylamine || Psychedelic

|-

| [[2C-T-7]] || || || || OCH3 || || S-CH2CH2CH3 || OCH3 || 2,5-dimethoxy-4-propylthio-phenethylamine || Psychedelic

|-

| [[2C-T-8]] || || || || OCH3 || || S-CH2-[[cyclopropyl|C3H5]] || OCH3 || 2,5-dimethoxy-4-[[cyclopropyl]]<nowiki>methylthio</nowiki>-phenethylamine || Psychedelic

|-

| [[2C-T-9]] || || || || OCH3 || || S-C(CH3)3 || OCH3 || 2,5-dimethoxy-4-''tert''-butylthio-phenethylamine || Psychedelic

|-

| [[2C-T-21]] || || || || OCH3 || || S-CH2-CH2-F || OCH3 || 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine || Psychedelic and [[euphoriant]]

|-

| [[25B-NBOMe]] ||CH2-C6H4-OCH3 || || || OCH3 || || Br || OCH3 || 2-(4-bromo-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic

|-

| [[25C-NBOMe]] ||CH2-C6H4-OCH3 || || || OCH3 || || Cl || OCH3 || 2-(4-chloro-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic

|-

| [[25I-NBOMe]] ||CH2-C6H4-OCH3 || || || OCH3 || || I || OCH3 || 2-(4-iodo-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic

|-

| [[25D-NBOMe]] ||CH2-C6H4-OCH3 || || || OCH3 || || CH2 || OCH3 || 2-(4-methyl-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic

|-

| [[25E-NBOMe]] ||CH2-C6H4-OCH3 || || || OCH3 || || CH2-CH3 || OCH3 || 2-(4-ethyl-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic

|-

| [[25P-NBOMe]] ||CH2-C6H4-OCH3 || || || OCH3 || || CH2-CH3-CH3 || OCH3 || 2-(4-propyl-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic

|-

| [[25F-NBOMe]] ||CH2-C6H4-OCH3 || || || OCH3 || || F || OCH3 || 2-(4-fluoro-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine || Psychedelic

|-

| [[Mescaline-NBOMe]] ||CH2-C6H4-OCH3 || || || || [[methoxy|OCH3]] || OCH3 || OCH3 || ''N''-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanamine || Psychedelic

|-

|[[25I-NBOH]]|| CH2–C6H4–OH || || || OCH3 || || I || OCH3 || ''N''-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine || Psychedelic

|-

|[[25C-NBOH]]|| CH2–C6H4–OH || || || OCH3 || || Cl || OCH3 || ''N''-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine || Psychedelic

|-

|[[25B-NBOH]]|| CH2–C6H4–OH || || || OCH3 || || Br || OCH3 || ''N''-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine || Psychedelic

|-

|[[25I-NBF]]|| CH2–C6H4–F || || || OCH3 || || I || OCH3 || ''N''-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine || Psychedelic

|-

|-class="sortbottom"

! Short Name

! ''RN''

! ''Rα''

! ''Rβ''

! ''R2''

! ''R3''

! ''R4''

! ''R5''

! Full Name

|}

==Pharmacology==

Phenethylamines are believed to produce their psychedelic effect primarily by partial agonism of [[Serotonin#The 5-HT System|5-HT2A receptors]].

Several [[neurotransmitter]]s are derived from phenethylamine, such as:

*[[Adrenaline]]

*[[Dopamine]]

*[[Noradrenaline]]

[[Category:Psychedelic]]

@@ Line 1: / Line 1: @@
+[[File:SubstitutedPhenethylamine.png|thumb|right|280px||Substitutive structure of a ''phenethylamine'' molecule.]]
+'''Substituted phenethylamine''' refers to a class of compounds which typically produce strong psychedelic effects.
+==Chemistry==
+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.
+Phenethylamines, tabulated by structure (from [[wikipedia:Tryptamine|Wikipedia]])
+{| class="wikitable sortable mw-collapsible collapsed"
+|-
+! Short Name
+! ''R<sup>N</sup>''
+! ''R<sup>α</sup>''
+! ''R<sup>β</sup>''
+! ''R<sup>2</sup>''
+! ''R<sup>3</sup>''
+! ''R<sup>4</sup>''
+! ''R<sup>5</sup>''
+! Full Name
+! Biologic activity
+|-
+| [[Tyramine|''meta''-Tyramine]] || || || || || [[Hydroxyl|OH]] || || || 3-hydroxyphenethylamine || [[Trace amine]]
+|-
+| [[Tyramine|''para''-Tyramine]] || || || || || || OH || || 4-hydroxyphenethylamine || [[Trace amine]]
+|-
+| [[Dopamine]] || || || || || OH || OH || || 3,4-dihydroxyphenethylamine || Catecholamine neurotransmitter
+|-
+| [[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
+|-
+| [[Norepinephrine]] (Noradrenaline) || || || OH || || OH || OH || || β,3,4-trihydroxyphenethylamine || Catecholamine neurotransmitter/Fight or Flight hormone
+|-
+| [[Norfenefrine|''meta''-Octopamine]] || || || OH || || OH || || || β,3-dihydroxyphenethylamine || [[Trace amine]]
+|-
+| [[Octopamine|''para''-Octopamine]] || || || OH || || || OH || || β,4-dihydroxyphenethylamine || [[Trace amine|Trace aminergic]] [[α-adrenoceptor]] agonist
+|-
+| [[Phenylephrine]] || CH<sub>3</sub> || || OH || || OH || || || β,3-dihydroxy-''N''-methylphenethylamin || α-adrenergic agonist;  [[decongestant]]
+|-
+| [[6-Hydroxydopamine]] || || || || OH || || OH || OH || 2,4,5-trihydroxyphenethylamine || neurotoxic agent for the [[dopamine]] and [[norepinephrine]] receptors
+|-
+| [[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]]
+|-
+| [[β-Methylphenethylamine]] || || || CH<sub>3</sub> || || || || || β-methylphenethylamine || Stimulant
+|-
+| [[Amphetamine]] || || CH<sub>3</sub> || || || || || || α-methylphenethylamine || [[Monoamine]] [[releasing agent]]; [[Stimulant]]
+|-
+| [[N-Methylphenethylamine]] || CH<sub>3</sub>|| || || || || || ||''N''-methylphenethylamine || Endogenous amphetamine isomer; [[Trace amine]]
+|-
+| [[Methamphetamine]] || CH<sub>3</sub>|| CH<sub>3</sub> || || || || || || ''N''-methylamphetamine || [[Monoamine]] [[releasing agent]]; [[Stimulant]]; dopaminergic neurotoxin
+|-
+| [[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]]
+|-
+| [[Ephedrine]] / [[Pseudoephedrine]] || CH<sub>3</sub>|| CH<sub>3</sub> || OH || || || || || ''N''-methyl-β-hydroxyamphetamine || [[Releasing agent]]; [[stimulant]]; [[decongestant]]
+|-
+| [[Cathine]] || || CH<sub>3</sub> || OH || || || || ||  d-β-hydroxyamphetamine || Somewhat selective [[norepinephrine releasing agent]]
+|-
+| [[Cathinone]] || || CH<sub>3</sub> || =O || || || || || β-ketoamphetamine || Selective norepinephrine and dopamine [[releasing agent]]
+|-
+| [[Methcathinone]] || CH<sub>3</sub> || CH<sub>3</sub> || =O || || || || || ''N''-methylcathinone || Selective norepinephrine and dopamine [[releasing agent]]
+|-
+| [[Mephedrone]] || CH<sub>3</sub> || CH<sub>3</sub> || =O || || || CH<sub>3</sub> || || 4-methylmethcathinone || Stimulant, unknown pharmacodynamics actions
+|-
+| [[Ethcathinone]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || =O || || || || || ''N''-ethylcathinone || Stimulant and Norepinephrine releasing agent
+|-
+| [[Bupropion]] || C(CH<sub>3</sub>)<sub>3</sub>|| CH<sub>3</sub> || =O || || [[chlorine|Cl]] || ||  || 3-[[chloro]]-''N''-''tert''-butyl-β-ketoamphetamine || NDRI
+|-
+| [[Norfenfluramine]] || || CH<sub>3</sub> || || || [[trifluoromethyl|CF<sub>3</sub>]] || || || 3-[[trifluoromethyl]]-amphetamine || [[Selective serotonin releasing agent|SSRA]]
+|-
+| [[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]]
+|-
+| [[Phentermine]] || || 2CH<sub>3</sub> || || || || || ||  α,α-dimethylphenethylamine || Stimulant, anorectic
+|-
+| [[5-(2-aminopropyl)benzofuran|5-APB]] || || CH<sub>3</sub> || || ||colspan=2| -CH=CH-O- || || 5-(2-aminopropyl)benzofuran || [[stimulant]], [[entactogen]]
+|-
+| [[6-(2-aminopropyl)benzofuran|6-APB]] || || CH<sub>3</sub> || || ||colspan=2| -O-CH=CH- || || 6-(2-aminopropyl)benzofuran || [[stimulant]], [[entactogen]]
+|-
+| [[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]]
+|-
+| [[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]]
+|-
+| [[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]]
+|-
+| [[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]]
+|-
+| [[Mescaline]] || || || || || [[methoxy|OCH<sub>3</sub>]] || OCH<sub>3</sub> || OCH<sub>3</sub> ||  3,4,5-tri[[methoxy]]<nowiki>phenethylamine</nowiki> || Serotonergic [[Psychedelic]]
+|-
+| [[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]]
+|-
+| [[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]]
+|-
+| [[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]]
+|-
+| [[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]]
+|-
+| [[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]]
+|-
+| [[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
+|-
+| [[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]]
+|-
+| [[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]]
+|-
+| [[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]]
+|-
+| [[2C-B]] || || || || OCH<sub>3</sub> || || Br || OCH<sub>3</sub> || 2,5-dimethoxy-4-bromophenethylamine|| [[Psychedelic drug|Psychedelic]], [[stimulant]], [[entactogen]] and [[euphoriant]]
+|-
+| [[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]]
+|-
+| [[2C-C]] || || || || OCH<sub>3</sub> || || Cl || OCH<sub>3</sub> || 2,5-dimethoxy-4-chlorophenethylamine|| [[Psychedelic drug|Psychedelic]]
+|-
+| [[2C-I]] || || || || OCH<sub>3</sub> || || I || OCH<sub>3</sub> || 2,5-dimethoxy-4-iodophenethylamine|| [[Psychedelic drug|Psychedelic]], [[stimulant]]
+|-
+| [[2C-D]] || || || || OCH<sub>3</sub> || || CH<sub>3</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-methylphenethylamine || [[Psychedelic drug|Psychedelic]], [[stimulant]]
+|-
+| [[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]]
+|-
+| [[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
+|-
+| [[2C-F]] || || || || OCH<sub>3</sub> || || [[fluorine|F]] || OCH<sub>3</sub> || 2,5-dimethoxy-4-[[fluoro]]<nowiki>phenethylamine</nowiki> || None
+|-
+| [[2C-N]] || || || || OCH<sub>3</sub> || || NO<sub>2</sub> || OCH<sub>3</sub> || 2,5-dimethoxy-4-nitrophenethylamine || [[euphoriant]]
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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]]
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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
+|-
+| [[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
+|-
+|[[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
+|-
+|[[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
+|-
+|[[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
+|-
+|[[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
+|-
+|-class="sortbottom"
+! Short Name
+! ''R<sup>N</sup>''
+! ''R<sup>α</sup>''
+! ''R<sup>β</sup>''
+! ''R<sup>2</sup>''
+! ''R<sup>3</sup>''
+! ''R<sup>4</sup>''
+! ''R<sup>5</sup>''
+! Full Name
+|}
+==Pharmacology==
+Phenethylamines are believed to produce their psychedelic effect primarily by partial agonism of [[Serotonin#The 5-HT System|5-HT<sub>2A</sub> receptors]].
+Several [[neurotransmitter]]s are derived from phenethylamine, such as:
+*[[Adrenaline]]
+*[[Dopamine]]
+*[[Noradrenaline]]
 [[Category:Psychedelic]]