Substituted amphetamines: Difference between revisions

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[[File:Substituted_amphetamine.svg|thumb|right|301px||Substitutive structure of an ''amphetamine'' molecule.]]

'''Substituted amphetamines''' ~~(also known as '''amphetamines''')~~ are a class of compounds ~~with molecular structures~~ based upon ~~that~~ the ~~molecular structure of~~ [[amphetamine]]. The class ~~includes many~~ [[~~Psychoactive substance index|psychoactive substances~~]], ~~which typically produce~~ [[~~stimulant~~]] ~~effects~~, [[~~entactogen|entactogenic~~]] ~~effects~~, and~~/or~~ [[~~psychedelic~~]] ~~effects~~.

'''Substituted amphetamines''' are a [[chemical class]] of organic compounds based upon the [[amphetamine]] chemical structure. The members of this class span a variety of pharmacological sub-classes, most prominently [[stimulants]] and [[entactogens]], but also some [[psychedelics]]. Examples of substituted amphetamines are [[amphetamine]] (itself), [[methamphetamine]], [[cathinone]], [[pyrovalerone]], [[MDMA]], and [[DOx]].

==Chemistry==

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Psychoactive substances of the substituted amphetamine class typically produce effects through [[dopamine|dopaminergic]], [[serotonin|serotonergic]], and [[norepinephrine|adrenergic]] pathways. Psychedelic effects can be attributed to action on the [[Serotonin#The 5-HT system|5-HT2A receptor]].{{citation needed}} Stimulant and entactogenic effects are due to their action as [[Releasing Agent|releasing agents]] of [[dopamine]], [[serotonin]], [[epinephrine]] and [[norepinephrine]] or as [[Agonist#Agonists|agonists]] on the receptors of the previous neurotransmitters.{{citation needed}} The agonism of this set of receptors leads to an increased rate firing of the post-synaptic neuron, triggering both [[Thought acceleration|cognitive]] and [[Stimulation|physical stimulation]] within the user.{{citation needed}}

== List of substituted amphetamines ==

==List of substituted amphetamines==

{| class="wikitable"

{| class="wikitable mw-collapsible"

|-

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

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

! scope="col" style="width: 50px;" | '''R2'''

! scope="col" style="width: 50px;" |'''R2'''

! scope="col" style="width: 50px;" | '''R3'''

! scope="col" style="width: 50px;" |'''R3'''

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

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

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

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

! scope="col" style="width: 50px;" | '''R6'''

! scope="col" style="width: 50px;" |'''R6'''

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

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

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

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

! scope="col" style="width: 200px;" | '''RN1'''

! scope="col" style="width: 200px;" |'''RN1'''

! scope="col" style="width: 200px;" | '''RN2'''

! scope="col" style="width: 200px;" |'''RN2'''

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

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

|-

| [[Amphetamine]] || H || H || H || H || H || H || H || H || H || [[File:Amphetamine.svg|170px]]

|[[Amphetamine]]||H||H||H||H||H||H||H||H||H||[[File:Amphetamine.svg|170px]]

|-

| [[Methamphetamine]] || H || H || H || H || H || H || H || H || CH3 || [[File:Methamphetamine.svg|170px]]

|[[Methamphetamine]]||H||H||H||H||H||H||H||H||CH3||[[File:Methamphetamine.svg|170px]]

|-

| ~~Ethylamphetamine (''Etilamfetamine'')~~ || H || H || H || H || H || H || H || H || ~~CH2~~CH3 || [[File:~~Ethylamphetamine~~.svg|170px]]

|[[Dextromethamphetamine]]||H||H||H||H||H||H||H||H||CH3||[[File:Dextromethamphetamine.svg|170px]]

|-

| ~~Propylamphetamine~~ || H || H || H || H || H || H || H || H || ~~CH2CH2~~CH3 || [[File:~~Propylamphetamine~~.svg|170px]]

|[[Levomethamphetamine]]||H||H||H||H||H||H||H||H||CH3||[[File:Levomethamphetamine.svg|170px]]

|-

| ~~Isopropylamphetamine~~ || H || H || H || H || H || H || H || H || ~~CH(~~CH3)2 || [[File:~~Isopropylamphetamine~~.svg|170px]]

|[[Ethylamphetamine]] (''Etilamfetamine'')||H||H||H||H||H||H||H||H||CH2CH3||[[File:Ethylamphetamine.svg|170px]]

|-

| [[~~Bromo-DragonFLY~~]] || ~~OCH=CH-~~ || - || Br || ~~OCH=CH-~~ || - || H || H || H || H || [[File:~~Bromo-DragonFLY~~.svg|170px]]

|[[Propylamphetamine]]||H||H||H||H||H||H||H||H||CH2CH2CH3||[[File:Propylamphetamine.svg|170px]]

|-

| [[~~Lisdexamfetamine~~]] || H || H || H || H || H || H || H || H || ~~COCH(NH2)~~(CH2)~~4NH~~2 || [[File:~~Lisdexamfetamine~~.svg|170px]]

|[[Isopropylamphetamine]]||H||H||H||H||H||H||H||H||CH(CH3)2||[[File:Isopropylamphetamine.svg|170px]]

|-

| ~~Clobenzorex~~ || H || H || H || H || H || H || H || H || ~~CH2C6~~H~~4Cl~~ || [[File:~~Clobenzorex~~.svg|170px]]

|[[Bromo-DragonFLY]]||OCH=CH-||-||Br||OCH=CH-||-||H||H||H||H||[[File:Bromo-DragonFLY.svg|170px]]

|-

| ~~Dimethylamphetamine~~ || H || H || H || H || H || H || H || CH3 ~~|| CH~~3 || [[File:~~Dimethylamphetamine~~.svg|170px]]

|[[Lisdexamfetamine]]||H||H||H||H||H||H||H||H||COCH(NH2)(CH2)4NH2||[[File:Lisdexamfetamine.svg|170px]]

|-

| ~~Selegiline~~ || H || H || H || H || H || H || H || CH3 ~~|| CH~~2~~CCH~~ || [[File:~~Selegiline~~.svg|170px]]

|[[Fenethylline]]||H||H||H||H||H||H||H||H||C9H12N4O2||[[File:Fenethylline.svg|170px]]

|-

| ~~Benzphetamine~~ || H || H || H || H || H || H || H || ~~CH3~~ || CH2C6H5 || [[File:~~Benzphetamine~~.svg|170px]]

|[[Clobenzorex]]||H||H||H||H||H||H||H||H||CH2C6H4Cl||[[File:Clobenzorex.svg|170px]]

|-

| ~~Ortetamine~~ || ~~CH3~~ || H || H || H || H || H || H || H || H || [[File:~~Ortetamine~~.svg|170px]]

|[[Dimethylamphetamine]]||H||H||H||H||H||H||H||CH3||CH3||[[File:Dimethylamphetamine.svg|170px]]

|-

| ~~3-Methylamphetamine~~ || H || ~~CH3~~ || H || H || H || H || H || H || H || [[File:~~3-Methylamphetamine~~.svg|170px]]

|[[Selegiline]]||H||H||H||H||H||H||H||CH3||CH2CCH||[[File:Selegiline.svg|170px]]

|-

| ~~4-Methylamphetamine~~ || H || H || ~~CH3~~ || H || H || H || H || H || H || [[File:~~4-Methylamphetamine~~.svg|170px]]

|[[Benzphetamine]]||H||H||H||H||H||H||H||CH3||CH2C6H5||[[File:Benzphetamine.svg|170px]]

|-

| ~~4-MMA || H || H~~ || CH3 || H || H || H || H || H || ~~CH3~~ || [[File:~~4-Methylmethamphetamine~~.svg|170px]]

|[[Ortetamine]]||CH3||H||H||H||H||H||H||H||H||[[File:Ortetamine.svg|170px]]

|-

| ~~Xylopropamine~~ || H || CH3 || ~~CH3~~ || H || H || H || H || H || H || [[File:~~Xylopropamine~~.svg|170px]]

|[[3-Methylamphetamine]]||H||CH3||H||H||H||H||H||H||H||[[File:3-Methylamphetamine.svg|170px]]

|-

| β-~~methylamphetamine~~ || H || H || H || H || H || H || ~~CH3~~ || H || H || [[File:β-~~methylamphetamine~~.svg|170px]]

|[[4-Methylamphetamine]]||H||H||CH3||H||H||H||H||H||H||[[File:4-Methylamphetamine.svg|170px]]

|-

| β-~~phenylmethamphetamine~~ || H || H || H || H || H || H || ~~C6~~H~~5~~ || H || ~~CH3~~ || [[File:β-~~phenylmethamphetamine~~.svg|170px]]

|[[3-MMA]]||H||CHз||H||H||H||H||H||H||CHз||[[File:3-Methylmethamphetamine.svg|170px]]

|-

| [[2-FA]] || F || H || H || H || H || H || H || H || H || [[File:2-FA.svg|170px]]

|[[4-MMA]]||H||H||CH3||H||H||H||H||H||CH3||[[File:4-Methylmethamphetamine.svg|170px]]

|-

| [[~~2-FMA~~]] || F || H || H || H || H || H || H || H || ~~CH3~~ || [[File:~~2-FMA~~.svg|170px]]

|[[Xylopropamine]]||H||CH3||CH3||H||H||H||H||H||H||[[File:Xylopropamine.svg|170px]]

|-

| [[2-~~FEA~~]] ~~|| F || H~~ || H || H || H || H || H || H || ~~CH2~~CH3 || [[File:2-~~FEA~~.svg|170px]]

|[[β-methylamphetamine]]||H||H||H||H||H||H||CH3||H||H||[[File:β-methylamphetamine.svg|170px]]

|-

| [[3-FA]] || H || F || H || H || H || H || H || H || H || [[File:3-FA.svg|170px]]

|[[β-phenylmethamphetamine]]||H||H||H||H||H||H||C6H5||H||CH3||[[File:β-phenylmethamphetamine.svg|170px]]

|-

| [[3-~~FMA~~]] || H || F || H || H || H || H || H || H || ~~CH3~~ || [[File:3-~~FMA~~.svg|170px]]

|[[2-FA]]||F||H||H||H||H||H||H||H||H||[[File:2-FA.svg|170px]]

|-

| [[3-~~FEA~~]] || H || F || H || H || H || H || H || H || ~~CH2~~CH3 || [[File:3-~~FEA~~.svg|170px]]

|[[2-FMA]]||F||H||H||H||H||H||H||H||CH3||[[File:2-FMA.svg|170px]]

|-

| ~~Fenfluramine~~ || H || ~~CF3~~ || H || H || H || H || H || H || CH2CH3 || [[File:~~Fenfluramine~~.svg|170px]]

|[[2-FEA]]||F||H||H||H||H||H||H||H||CH2CH3||[[File:2-FEA.svg|170px]]

|-

| ~~Norfenfluramine~~ || H || ~~CF3~~ || H || H || H || H || H || H || H || [[File:~~Norfenfluramine~~.svg|170px]]

|[[3-FA]]||H||F||H||H||H||H||H||H||H||[[File:3-FA.svg|170px]]

|-

| [[4-FA]] || H || H || F || H || H || H || H || H || H || [[File:4-FA.svg|170px]]

|[[3-FMA]]||H||F||H||H||H||H||H||H||CH3||[[File:3-FMA.svg|170px]]

|-

| [[4-~~FMA~~]] || H || H || F || H || H || H || H || H || CH3 || [[File:4-~~FMA~~.svg|170px]]

|[[3-FEA]]||H||F||H||H||H||H||H||H||CH2CH3||[[File:3-FEA.svg|170px]]

|-

| ~~4-CA~~ || H || H || Cl || H || H || H || H || H || H || [[File:~~4-CA~~.svg|170px]]

|[[Fenfluramine]]||H||CF3||H||H||H||H||H||H||CH2CH3||[[File:Fenfluramine.svg|170px]]

|-

| ~~4-BA~~ || H || H || Br || H || H || H || H || H || H || [[File:~~4-BA~~.svg|170px]]

|[[Norfenfluramine]]||H||CF3||H||H||H||H||H||H||H||[[File:Norfenfluramine.svg|170px]]

|-

| 4-IA || H || H || I || H || H || H || H || H || H || [[File:4-IA.svg|170px]]

|[[4-FA]]||H||H||F||H||H||H||H||H||H||[[File:4-FA.svg|170px]]

|-

| ~~DCA~~ || H || Cl || Cl || H || H || H || H || H || H || [[File:~~DCA~~.svg|170px]]

|[[4-FMA]]||H||H||F||H||H||H||H||H||CH3||[[File:4-FMA.svg|170px]]

|-

| 4-HA || H || H || OH || H || H || H || H || H || H || [[File:4-HA.svg|170px]]

|[[3-CMA]]||H||H||H||Cl||H||H||H||H||H||[[File:3-CMA.svg|170px]]

|-

| 4-~~HMA~~ || H || H || OH || H || H || H || H || H || ~~CH3~~ || [[File:4-~~HMA~~.svg|170px]]

|[[4-CA]]||H||H||Cl||H||H||H||H||H||H||[[File:4-CA.svg|170px]]

|-

| 3,4-~~DHA~~ || H || OH || OH || H || H || H || H || H || H || [[File:3,4-~~DHA~~.svg|170px]]

|[[4-BA]]||H||H||Br||H||H||H||H||H||H||[[File:4-BA.svg|170px]]

|-

| ~~OMA~~ || ~~OCH3~~ || H || H || H || H || H || H || H || H || [[File:~~OMA~~.svg|170px]]

|[[4-IA]]||H||H||I||H||H||H||H||H||H||[[File:4-IA.svg|170px]]

|-

| ~~3-MA~~ || H || ~~OCH3~~ || H || H || H || H || H || H || H || [[File:~~3-MA~~.svg|170px]]

|[[DCA]]||H||Cl||Cl||H||H||H||H||H||H||[[File:DCA.svg|170px]]

|-

| ~~MMMA~~ || H || ~~OCH3~~ || H || H || H || H || H || H || ~~CH3~~ || [[File:~~MMMA~~.svg|170px]]

|[[4-HA]]||H||H||OH||H||H||H||H||H||H||[[File:4-HA.svg|170px]]

|-

| ~~MMA~~ || H || ~~OCH3~~ || ~~CH3~~ || H || H || H || H || H || H || [[File:~~MMA~~.svg|170px]]

|[[4-HMA]]||H||H||OH||H||H||H||H||H||CH3||[[File:4-HMA.svg|170px]]

|-

| [[~~PMA~~]] || H || H || ~~OCH3~~ || H || H || H || H || H || H || [[File:~~PMA~~.svg|~~171px~~]]

|[[3,4-DHA]]||H||OH||OH||H||H||H||H||H||H||[[File:3,4-DHA.svg|170px]]

|-

| [[~~PMMA~~]] ~~|| H || H~~ || OCH3 || H || H || H || H || H || ~~CH3~~ || [[File:~~PMMA~~.svg|~~171px~~]]

|[[OMA]]||OCH3||H||H||H||H||H||H||H||H||[[File:OMA.svg|170px]]

|-

| ~~PMEA || H~~ || H || OCH3 || H || H || H || H || H || ~~CH2CH3~~ || [[File:~~PMEA~~.svg|170px]]

|[[3-MA]]||H||OCH3||H||H||H||H||H||H||H||[[File:3-MA.svg|170px]]

|-

| ~~4-ETA || H~~ || H || OCH~~2CH~~3 || H || H || H || H || H || H || [[File:~~4-ETA~~.svg|170px]]

|[[MMMA]]||H||OCH3||H||H||H||H||H||H||CH3||[[File:MMMA.svg|170px]]

|-

| [[~~TMA-6~~]] || OCH3 || ~~H || OCH~~3 || H || ~~OCH3~~ || H || H || H || H || [[File:~~TMA-6~~.svg|170px]]

|[[MMA]]||H||OCH3||CH3||H||H||H||H||H||H||[[File:MMA.svg|170px]]

|-

| ~~4-MTA~~ || H || H || ~~SCH~~3 || H || H || H || H || H || H || [[File:~~4-MTA~~.svg|~~170px~~]]

|[[PMA]]||H||H||OCH3||H||H||H||H||H||H||[[File:PMA.svg|171px]]

|-

| ~~Cathine~~ || H || H || H || H || H || H || OH || H || H || [[File:~~Cathine~~.svg|~~170px~~]]

|[[PMMA]]||H||H||OCH3||H||H||H||H||H||CH3||[[File:PMMA.svg|171px]]

|-

| Phenmetrazine || H || H || H || H || H || H || OCH2- || CH2- || H || [[File:Phenmetrazine.svg|170px]]

|[[PMEA]]||H||H||OCH3||H||H||H||H||H||CH2CH3||[[File:PMEA.svg|170px]]

|-

|[[4-ETA]]||H||H||OCH2CH3||H||H||H||H||H||H||[[File:4-ETA.svg|170px]]

|-

|[[TMA]]||H||OCH3||OCH3||OCH3||H||H||H||H||H||[[File:TMA-1.svg|170px]]

|-

|[[TMA-2]]||OCH3||H||OCH3||OCH3||H||H||H||H||H||[[File:TMA-2.svg|170px]]

|-

|[[TMA-6]]||OCH3||H||OCH3||H||OCH3||H||H||H||H||[[File:TMA-6.svg|170px]]

|-

|[[4-MTA]]||H||H||SCH3||H||H||H||H||H||H||[[File:4-MTA.svg|170px]]

|-

|[[5-API]]||H||CH=CH-||NH-||H||H||H||H||H||H||[[File:5-API.svg|170px]]

|-

|[[Cathine]]||H||H||H||H||H||H||OH||H||H||[[File:Cathine.svg|170px]]

|-

|[[Pseudoephedrine]]||H||H||H||H||H||H||OH||H||CH3||[[File:Pseudoephedrine.svg|170px]]

|-

|[[Phenmetrazine]]||H||H||H||H||H||H||OCH2-||CH2-||H||[[File:Phenmetrazine.svg|170px]]

|-

|[[3-FPM]]||H||F||H||H||H||H||OCH2-||CH2-||H||[[File:3-FPM.svg|170px]]

|-

|[[PPAP]]||H||H||H||H||H||CH2CH3||H||H||CH2CH2CH3||[[File:PPAP.svg|170px]]

|-

|[[Prolintane]]||H||H||H||H||H||CH2CH3||H||CH2CH2-||CH2CH2-||[[File:Prolintane.svg|170px]]

|-

|}

==See also==

*[[Responsible use]]

*[[Phenethylamine]]

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==External links==

*[[wikipedia:Substituted amphetamine|Substituted amphetamine (Wikipedia)]]

==References==

[[Category:Chemical class]]

[[Category:Amphetamine|*]]

@@ Line 1: / Line 1: @@
 [[File:Substituted_amphetamine.svg|thumb|right|301px||Substitutive structure of an ''amphetamine'' molecule.]]
-'''Substituted amphetamines''' (also known as '''amphetamines''') are a class of compounds with molecular structures based upon that the molecular structure of [[amphetamine]]. The class includes many [[Psychoactive substance index|psychoactive substances]], which typically produce [[stimulant]] effects, [[entactogen|entactogenic]] effects, and/or [[psychedelic]] effects.
+'''Substituted amphetamines''' are a [[chemical class]] of organic compounds based upon the [[amphetamine]] chemical structure. The members of this class span a variety of pharmacological sub-classes, most prominently [[stimulants]] and [[entactogens]], but also some [[psychedelics]]. Examples of substituted amphetamines are [[amphetamine]] (itself), [[methamphetamine]], [[cathinone]], [[pyrovalerone]], [[MDMA]], and [[DOx]].
 ==Chemistry==
@@ Line 10: / Line 10: @@
 Psychoactive substances of the substituted amphetamine class typically produce effects through [[dopamine|dopaminergic]], [[serotonin|serotonergic]], and [[norepinephrine|adrenergic]] pathways. Psychedelic effects can be attributed to action on the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]].{{citation needed}} Stimulant and entactogenic effects are due to their action as [[Releasing Agent|releasing agents]] of [[dopamine]], [[serotonin]], [[epinephrine]] and [[norepinephrine]] or as [[Agonist#Agonists|agonists]] on the receptors of the previous neurotransmitters.{{citation needed}} The agonism of this set of receptors leads to an increased rate firing of the post-synaptic neuron, triggering both [[Thought acceleration|cognitive]] and [[Stimulation|physical stimulation]] within the user.{{citation needed}}
-== List of substituted amphetamines ==
+==List of substituted amphetamines==
-''Note: This list does not include [[Phenidate|phenidates]], [[Substituted cathinone|cathinones]], [[Substituted MDxx|MDxxs]], [[DOx|DOxs]], [[Benzofuran|Benzofurans]], or [[Substituted aminoindane|aminoindanes]].''
+''Note: This list does not include [[Phenidate|phenidates]], [[Substituted cathinone|cathinones]], [[pyrrolidinophenone|pyrrolidinophenones]] [[MDxx|MDxxs]], [[DOx|DOxs]], [[benzofurans]] among other further substituted amphetamines.''
-{| class="wikitable"
+{| class="wikitable mw-collapsible"
 |-
-! scope="col" | '''Compound'''
+! scope="col" |'''Compound'''
-! scope="col" style="width: 50px;" | '''R<sub>2</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>2</sub>'''
-! scope="col" style="width: 50px;" | '''R<sub>3</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>3</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>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" style="width: 50px;" |'''R<sub>β</sub>'''
-! scope="col" style="width: 200px;" | '''R<sub>N1</sub>'''
+! scope="col" style="width: 200px;" |'''R<sub>N1</sub>'''
-! scope="col" style="width: 200px;" | '''R<sub>N2</sub>'''
+! scope="col" style="width: 200px;" |'''R<sub>N2</sub>'''
-! scope="col" | '''Structure'''
+! scope="col" |'''Structure'''
 |-
-| [[Amphetamine]] || H || H || H || H || H || H || H || H || H || [[File:Amphetamine.svg|170px]]
+|[[Amphetamine]]||H||H||H||H||H||H||H||H||H||[[File:Amphetamine.svg|170px]]
 |-
-| [[Methamphetamine]] || H || H || H || H || H || H || H || H || CH<sub>3</sub> || [[File:Methamphetamine.svg|170px]]
+|[[Methamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Methamphetamine.svg|170px]]
 |-
-| Ethylamphetamine (''Etilamfetamine'') || H || H || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:Ethylamphetamine.svg|170px]]
+|[[Dextromethamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Dextromethamphetamine.svg|170px]]
 |-
-| Propylamphetamine || H || H || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:Propylamphetamine.svg|170px]]
+|[[Levomethamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Levomethamphetamine.svg|170px]]
 |-
-| Isopropylamphetamine || H || H || H || H || H || H || H || H || CH(CH<sub>3</sub>)<sub>2</sub> || [[File:Isopropylamphetamine.svg|170px]]
+|[[Ethylamphetamine]] (''Etilamfetamine'')||H||H||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:Ethylamphetamine.svg|170px]]
 |-
-| [[Bromo-DragonFLY]] || OCH=CH- || - || Br || OCH=CH- || - || H || H || H || H || [[File:Bromo-DragonFLY.svg|170px]]
+|[[Propylamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||[[File:Propylamphetamine.svg|170px]]
 |-
-| [[Lisdexamfetamine]] || H || H || H || H || H || H || H || H || COCH(NH<sub>2</sub>)(CH<sub>2</sub>)<sub>4</sub>NH<sub>2</sub> || [[File:Lisdexamfetamine.svg|170px]]
+|[[Isopropylamphetamine]]||H||H||H||H||H||H||H||H||CH(CH<sub>3</sub>)<sub>2</sub>||[[File:Isopropylamphetamine.svg|170px]]
 |-
-| Clobenzorex || H || H || H || H || H || H || H || H || CH<sub>2</sub>C<sub>6</sub>H<sub>4</sub>Cl || [[File:Clobenzorex.svg|170px]]
+|[[Bromo-DragonFLY]]||OCH=CH-||-||Br||OCH=CH-||-||H||H||H||H||[[File:Bromo-DragonFLY.svg|170px]]
 |-
-| Dimethylamphetamine || H || H || H || H || H || H || H || CH<sub>3</sub> || CH<sub>3</sub> || [[File:Dimethylamphetamine.svg|170px]]
+|[[Lisdexamfetamine]]||H||H||H||H||H||H||H||H||COCH(NH<sub>2</sub>)(CH<sub>2</sub>)<sub>4</sub>NH<sub>2</sub>||[[File:Lisdexamfetamine.svg|170px]]
 |-
-| Selegiline || H || H || H || H || H || H || H || CH<sub>3</sub> || CH<sub>2</sub>CCH || [[File:Selegiline.svg|170px]]
+|[[Fenethylline]]||H||H||H||H||H||H||H||H||C<sub>9</sub>H<sub>12</sub>N<sub>4</sub>O<sub>2</sub>||[[File:Fenethylline.svg|170px]]
 |-
-| Benzphetamine || H || H || H || H || H || H || H || CH<sub>3</sub> || CH<sub>2</sub>C<sub>6</sub>H<sub>5</sub> || [[File:Benzphetamine.svg|170px]]
+|[[Clobenzorex]]||H||H||H||H||H||H||H||H||CH<sub>2</sub>C<sub>6</sub>H<sub>4</sub>Cl||[[File:Clobenzorex.svg|170px]]
 |-
-| Ortetamine || CH<sub>3</sub> || H || H || H || H || H || H || H || H || [[File:Ortetamine.svg|170px]]
+|[[Dimethylamphetamine]]||H||H||H||H||H||H||H||CH<sub>3</sub>||CH<sub>3</sub>||[[File:Dimethylamphetamine.svg|170px]]
 |-
-| 3-Methylamphetamine || H || CH<sub>3</sub> || H || H || H || H || H || H || H || [[File:3-Methylamphetamine.svg|170px]]
+|[[Selegiline]]||H||H||H||H||H||H||H||CH<sub>3</sub>||CH<sub>2</sub>CCH||[[File:Selegiline.svg|170px]]
 |-
-| 4-Methylamphetamine || H || H || CH<sub>3</sub> || H || H || H || H || H || H || [[File:4-Methylamphetamine.svg|170px]]
+|[[Benzphetamine]]||H||H||H||H||H||H||H||CH<sub>3</sub>||CH<sub>2</sub>C<sub>6</sub>H<sub>5</sub>||[[File:Benzphetamine.svg|170px]]
 |-
-| 4-MMA || H || H || CH<sub>3</sub> || H || H || H || H || H || CH<sub>3</sub> || [[File:4-Methylmethamphetamine.svg|170px]]
+|[[Ortetamine]]||CH<sub>3</sub>||H||H||H||H||H||H||H||H||[[File:Ortetamine.svg|170px]]
 |-
-| Xylopropamine || H || CH<sub>3</sub> || CH<sub>3</sub> || H || H || H || H || H || H || [[File:Xylopropamine.svg|170px]]
+|[[3-Methylamphetamine]]||H||CH<sub>3</sub>||H||H||H||H||H||H||H||[[File:3-Methylamphetamine.svg|170px]]
 |-
-| β-methylamphetamine || H || H || H || H || H || H || CH<sub>3</sub> || H || H || [[File:β-methylamphetamine.svg|170px]]
+|[[4-Methylamphetamine]]||H||H||CH<sub>3</sub>||H||H||H||H||H||H||[[File:4-Methylamphetamine.svg|170px]]
 |-
-| β-phenylmethamphetamine || H || H || H || H || H || H || C<sub>6</sub>H<sub>5</sub> || H || CH<sub>3</sub> || [[File:β-phenylmethamphetamine.svg|170px]]
+|[[3-MMA]]||H||CHз||H||H||H||H||H||H||CHз||[[File:3-Methylmethamphetamine.svg|170px]]
 |-
-| [[2-FA]] || F || H || H || H || H || H || H || H || H || [[File:2-FA.svg|170px]]
+|[[4-MMA]]||H||H||CH<sub>3</sub>||H||H||H||H||H||CH<sub>3</sub>||[[File:4-Methylmethamphetamine.svg|170px]]
 |-
-| [[2-FMA]] || F || H || H || H || H || H || H || H || CH<sub>3</sub> || [[File:2-FMA.svg|170px]]
+|[[Xylopropamine]]||H||CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||H||H||H||[[File:Xylopropamine.svg|170px]]
 |-
-| [[2-FEA]] || F || H || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:2-FEA.svg|170px]]
+|[[β-methylamphetamine]]||H||H||H||H||H||H||CH<sub>3</sub>||H||H||[[File:β-methylamphetamine.svg|170px]]
 |-
-| [[3-FA]] || H || F || H || H || H || H || H || H || H || [[File:3-FA.svg|170px]]
+|[[β-phenylmethamphetamine]]||H||H||H||H||H||H||C<sub>6</sub>H<sub>5</sub>||H||CH<sub>3</sub>||[[File:β-phenylmethamphetamine.svg|170px]]
 |-
-| [[3-FMA]] || H || F || H || H || H || H || H || H || CH<sub>3</sub> || [[File:3-FMA.svg|170px]]
+|[[2-FA]]||F||H||H||H||H||H||H||H||H||[[File:2-FA.svg|170px]]
 |-
-| [[3-FEA]] || H || F || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:3-FEA.svg|170px]]
+|[[2-FMA]]||F||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:2-FMA.svg|170px]]
 |-
-| Fenfluramine || H || CF<sub>3</sub> || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:Fenfluramine.svg|170px]]
+|[[2-FEA]]||F||H||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:2-FEA.svg|170px]]
 |-
-| Norfenfluramine || H || CF<sub>3</sub> || H || H || H || H || H || H || H || [[File:Norfenfluramine.svg|170px]]
+|[[3-FA]]||H||F||H||H||H||H||H||H||H||[[File:3-FA.svg|170px]]
 |-
-| [[4-FA]] || H || H || F || H || H || H || H || H || H || [[File:4-FA.svg|170px]]
+|[[3-FMA]]||H||F||H||H||H||H||H||H||CH<sub>3</sub>||[[File:3-FMA.svg|170px]]
 |-
-| [[4-FMA]] || H || H || F || H || H || H || H || H || CH<sub>3</sub> || [[File:4-FMA.svg|170px]]
+|[[3-FEA]]||H||F||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:3-FEA.svg|170px]]
 |-
-| 4-CA || H || H || Cl || H || H || H || H || H || H || [[File:4-CA.svg|170px]]
+|[[Fenfluramine]]||H||CF<sub>3</sub>||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:Fenfluramine.svg|170px]]
 |-
-| 4-BA || H || H || Br || H || H || H || H || H || H || [[File:4-BA.svg|170px]]
+|[[Norfenfluramine]]||H||CF<sub>3</sub>||H||H||H||H||H||H||H||[[File:Norfenfluramine.svg|170px]]
 |-
-| 4-IA || H || H || I || H || H || H || H || H || H || [[File:4-IA.svg|170px]]
+|[[4-FA]]||H||H||F||H||H||H||H||H||H||[[File:4-FA.svg|170px]]
 |-
-| DCA || H || Cl || Cl || H || H || H || H || H || H || [[File:DCA.svg|170px]]
+|[[4-FMA]]||H||H||F||H||H||H||H||H||CH<sub>3</sub>||[[File:4-FMA.svg|170px]]
 |-
-| 4-HA || H || H || OH || H || H || H || H || H || H || [[File:4-HA.svg|170px]]
+|[[3-CMA]]||H||H||H||Cl||H||H||H||H||H||[[File:3-CMA.svg|170px]]
 |-
-| 4-HMA || H || H || OH || H || H || H || H || H || CH<sub>3</sub> || [[File:4-HMA.svg|170px]]
+|[[4-CA]]||H||H||Cl||H||H||H||H||H||H||[[File:4-CA.svg|170px]]
 |-
-| 3,4-DHA || H || OH || OH || H || H || H || H || H || H || [[File:3,4-DHA.svg|170px]]
+|[[4-BA]]||H||H||Br||H||H||H||H||H||H||[[File:4-BA.svg|170px]]
 |-
-| OMA || OCH<sub>3</sub> || H || H || H || H || H || H || H || H || [[File:OMA.svg|170px]]
+|[[4-IA]]||H||H||I||H||H||H||H||H||H||[[File:4-IA.svg|170px]]
 |-
-| 3-MA || H || OCH<sub>3</sub> || H || H || H || H || H || H || H || [[File:3-MA.svg|170px]]
+|[[DCA]]||H||Cl||Cl||H||H||H||H||H||H||[[File:DCA.svg|170px]]
 |-
-| MMMA || H || OCH<sub>3</sub> || H || H || H || H || H || H || CH<sub>3</sub> || [[File:MMMA.svg|170px]]
+|[[4-HA]]||H||H||OH||H||H||H||H||H||H||[[File:4-HA.svg|170px]]
 |-
-| MMA || H || OCH<sub>3</sub> || CH<sub>3</sub> || H || H || H || H || H || H || [[File:MMA.svg|170px]]
+|[[4-HMA]]||H||H||OH||H||H||H||H||H||CH<sub>3</sub>||[[File:4-HMA.svg|170px]]
 |-
-| [[PMA]]  || H || H || OCH<sub>3</sub> || H || H || H || H || H || H || [[File:PMA.svg|171px]]
+|[[3,4-DHA]]||H||OH||OH||H||H||H||H||H||H||[[File:3,4-DHA.svg|170px]]
 |-
-| [[PMMA]] || H || H || OCH<sub>3</sub> || H || H || H || H || H || CH<sub>3</sub> || [[File:PMMA.svg|171px]]
+|[[OMA]]||OCH<sub>3</sub>||H||H||H||H||H||H||H||H||[[File:OMA.svg|170px]]
 |-
-| PMEA || H || H || OCH<sub>3</sub> || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:PMEA.svg|170px]]
+|[[3-MA]]||H||OCH<sub>3</sub>||H||H||H||H||H||H||H||[[File:3-MA.svg|170px]]
 |-
-| 4-ETA || H || H || OCH<sub>2</sub>CH<sub>3</sub> || H || H || H || H || H || H || [[File:4-ETA.svg|170px]]
+|[[MMMA]]||H||OCH<sub>3</sub>||H||H||H||H||H||H||CH<sub>3</sub>||[[File:MMMA.svg|170px]]
 |-
-| [[TMA-6]] || OCH<sub>3</sub> || H || OCH<sub>3</sub> || H || OCH<sub>3</sub> || H || H || H || H || [[File:TMA-6.svg|170px]]
+|[[MMA]]||H||OCH<sub>3</sub>||CH<sub>3</sub>||H||H||H||H||H||H||[[File:MMA.svg|170px]]
 |-
-| 4-MTA || H || H || SCH<sub>3</sub> || H || H || H || H || H || H || [[File:4-MTA.svg|170px]]
+|[[PMA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||H||[[File:PMA.svg|171px]]
 |-
-| Cathine || H || H || H || H || H || H || OH || H || H || [[File:Cathine.svg|170px]]
+|[[PMMA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||CH<sub>3</sub>||[[File:PMMA.svg|171px]]
 |-
-| Phenmetrazine || H || H || H || H || H || H || OCH<sub>2</sub>- || CH<sub>2</sub>- || H || [[File:Phenmetrazine.svg|170px]]
+|[[PMEA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:PMEA.svg|170px]]
+|-
+|[[4-ETA]]||H||H||OCH<sub>2</sub>CH<sub>3</sub>||H||H||H||H||H||H||[[File:4-ETA.svg|170px]]
+|-
+|[[TMA]]||H||OCH<sub>3</sub>||OCH<sub>3</sub>||OCH<sub>3</sub>||H||H||H||H||H||[[File:TMA-1.svg|170px]]
+|-
+|[[TMA-2]]||OCH<sub>3</sub>||H||OCH<sub>3</sub>||OCH<sub>3</sub>||H||H||H||H||H||[[File:TMA-2.svg|170px]]
+|-
+|[[TMA-6]]||OCH<sub>3</sub>||H||OCH<sub>3</sub>||H||OCH<sub>3</sub>||H||H||H||H||[[File:TMA-6.svg|170px]]
+|-
+|[[4-MTA]]||H||H||SCH<sub>3</sub>||H||H||H||H||H||H||[[File:4-MTA.svg|170px]]
+|-
+|[[5-API]]||H||CH=CH-||NH-||H||H||H||H||H||H||[[File:5-API.svg|170px]]
+|-
+|[[Cathine]]||H||H||H||H||H||H||OH||H||H||[[File:Cathine.svg|170px]]
+|-
+|[[Pseudoephedrine]]||H||H||H||H||H||H||OH||H||CH<sub>3</sub>||[[File:Pseudoephedrine.svg|170px]]
+|-
+|[[Phenmetrazine]]||H||H||H||H||H||H||OCH<sub>2</sub>-||CH<sub>2</sub>-||H||[[File:Phenmetrazine.svg|170px]]
+|-
+|[[3-FPM]]||H||F||H||H||H||H||OCH<sub>2</sub>-||CH<sub>2</sub>-||H||[[File:3-FPM.svg|170px]]
+|-
+|[[PPAP]]||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||H||H||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||[[File:PPAP.svg|170px]]
+|-
+|[[Prolintane]]||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||H||CH<sub>2</sub>CH<sub>2</sub>-||CH<sub>2</sub>CH<sub>2</sub>-||[[File:Prolintane.svg|170px]]
 |-
 |}
 ==See also==
 *[[Responsible use]]
 *[[Phenethylamine]]
@@ Line 130: / Line 155: @@
 ==External links==
 *[[wikipedia:Substituted amphetamine|Substituted amphetamine (Wikipedia)]]
 ==References==
 {{references}}
+[[Category:Chemical class]]
+[[Category:Amphetamine|*]]
+{{#set:Featured=true}}