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[[File:200px-Amphetamine_numbered.png|thumb|right|200px||General formula of amphetamine molecule.]]
[[File:Substituted_amphetamine.svg|thumb|right|301px||Substitutive structure of an ''amphetamine'' molecule.]]
'''Substituted amphetamines''', also known as '''amphetamines''', are a class of chemicals that include compounds with psychoactive 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==
==Chemistry==
Substituted amphetamines are a chemical class based upon the molecule [[amphetamine]]. Amphetamine is made up of a [[Substituted Phenethylamines|phenethylamine]] molecule. The chemical structure of a substituted amphetamine is the same as the organic molecule amphetamine, except some substitutions are made at the phenyl and amine sites, typically of methyl and ethyl chains.
[[File:Substituted_phenethylamine.svg|thumb|right|245px|Substitutive structure of a ''phenethylamine'' molecule.]]
 
Substituted amphetamines are a class of compounds that have structures based on that of [[amphetamine]] with different substitutions at various positions. An amphetamine molecule has the structure of a [[phenethylamine]] molecule with an additional methyl group located on the alpha carbon. Thus, in addition to being the unsubstituted member of the substituted amphetamine class, amphetamine is also considered a [[Phenethylamine|substituted phenethylamine]].


==Pharmacology==
==Pharmacology==
The substituted amphetamine class of [[psychedelic]], [[entactogenic]] and [[stimulant]] drugs works via their action upon numerous receptors. Psychedelic effects can be attributed to action on the [[Serotonin#The 5-HT System|5-HT<sub>2A</sub> receptor]]. Entactogenic and stimulant effects are due to their action as [[Releasing Agent|releasing agents]] of [[serotonin]], [[adrenaline]] and [[noradrenaline]]; or as [[Agonist#Agonists|agonists]] on the receptors of the previous neurotransmitters. 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.
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}}


==Examples==
==List of substituted amphetamines==
Substituted amphetamines are seen throughout organic chemistry, and include many psychoactive drugs.
''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 mw-collapsible"
{| class="wikitable sortable"
! Generic or Trivial Name
! Chemical Name
! # of Subs
|-
| [[Amphetamine]] || α-Methyl-phenethylamine || 0 |
|-
| [[Methamphetamine]] || ''N''-Methylamphetamine, (1''R'',2''S'')- || 1 |
|-
|-
| [[Etilamfetamine|Ethylamphetamine]] || ''N''-Ethylamphetamine || 1 |
! scope="col" |'''Compound'''
! 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>4</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>β</sub>'''
! scope="col" style="width: 200px;" |'''R<sub>N1</sub>'''
! scope="col" style="width: 200px;" |'''R<sub>N2</sub>'''
! scope="col" |'''Structure'''
|-
|-
| [[Propylamphetamine]] || ''N''-Propylamphetamine || 1 |
|[[Amphetamine]]||H||H||H||H||H||H||H||H||H||[[File:Amphetamine.svg|170px]]
|-
|-
| [[Isopropylamphetamine]] || ''N''-''iso''-Propylamphetamine || 1 |
|[[Methamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Methamphetamine.svg|170px]]
|-
|-
| [[Phentermine]] || α-Methylamphetamine || 1 |
|[[Dextromethamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Dextromethamphetamine.svg|170px]]
|-
|-
| [[Phenylpropanolamine]] (PPA) || β-Hydroxyamphetamine, (1''R'',2''S'')- || 1 |
|[[Levomethamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Levomethamphetamine.svg|170px]]
|-
|-
| [[Cathine]] || β-Hydroxyamphetamine, (1''S'',2''S'')- || 1 |
|[[Ethylamphetamine]] (''Etilamfetamine'')||H||H||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:Ethylamphetamine.svg|170px]]
|-
|-
| [[Cathinone]] || β-Ketoamphetamine || 1 |
|[[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]]
|-
|-
| [[Ortetamine]] || 2-Methylamphetamine || 1 |
|[[Isopropylamphetamine]]||H||H||H||H||H||H||H||H||CH(CH<sub>3</sub>)<sub>2</sub>||[[File:Isopropylamphetamine.svg|170px]]
|-
|-
| [[2-Fluoroamphetamine]] (2-FA) || 2-Fluoroamphetamine || 1 |
|[[Bromo-DragonFLY]]||OCH=CH-||-||Br||OCH=CH-||-||H||H||H||H||[[File:Bromo-DragonFLY.svg|170px]]
|-
|-
| [[3-Methylamphetamine]] (3-MA) || 3-Methylamphetamine || 1 |
|[[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]]
|-
|-
| [[3-Fluoroamphetamine]] (3-FA) || 3-Fluoroamphetamine || 1 |
|[[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]]
|-
|-
| [[Norfenfluramine]] || 3-Trifluoromethylamphetamine || 1 |
|[[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]]
|-
|-
| [[4-Methylamphetamine]] (4-MA) || 4-Methylamphetamine || 1 |
|[[Dimethylamphetamine]]||H||H||H||H||H||H||H||CH<sub>3</sub>||CH<sub>3</sub>||[[File:Dimethylamphetamine.svg|170px]]
|-
|-
| [[para-Methoxyamphetamine|''para''-Methoxyamphetamine]] (PMA) || 4-Methoxyamphetamine || 1 |
|[[Selegiline]]||H||H||H||H||H||H||H||CH<sub>3</sub>||CH<sub>2</sub>CCH||[[File:Selegiline.svg|170px]]
|-
|-
| [[para-Ethoxyamphetamine|''para''-Ethoxyamphetamine]] || 4-Ethoxyamphetamine || 1 |
|[[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-Methylthioamphetamine]] (4-MTA) || 4-Methylthioamphetamine || 1 |
|[[Ortetamine]]||CH<sub>3</sub>||H||H||H||H||H||H||H||H||[[File:Ortetamine.svg|170px]]
|-
|-
| [[Norpholedrine]] (α-Me-TRA) || 4-Hydroxyamphetamine || 1 |
|[[3-Methylamphetamine]]||H||CH<sub>3</sub>||H||H||H||H||H||H||H||[[File:3-Methylamphetamine.svg|170px]]
|-
|-
| [[para-Bromoamphetamine|''para''-Bromoamphetamine]] (PBA, 4-BA) || 4-Bromoamphetamine || 1 |
|[[4-Methylamphetamine]]||H||H||CH<sub>3</sub>||H||H||H||H||H||H||[[File:4-Methylamphetamine.svg|170px]]
|-
|-
| [[para-Chloroamphetamine|''para''-Chloroamphetamine]] (PCA, 4-CA) || 4-Chloroamphetamine || 1 |
|[[3-MMA]]||H||CHз||H||H||H||H||H||H||CHз||[[File:3-Methylmethamphetamine.svg|170px]]
|-
|-
| [[para-Fluoroamphetamine|''para''-Fluoroamphetamine]] (PFA, 4-FA, 4-FMP) || 4-Fluoroamphetamine || 1 |
|[[4-MMA]]||H||H||CH<sub>3</sub>||H||H||H||H||H||CH<sub>3</sub>||[[File:4-Methylmethamphetamine.svg|170px]]
|-
|-
| [[para-Iodoamphetamine|''para''-Iodoamphetamine]] (PIA, 4-IA) || 4-Iodoamphetamine || 1 |
|[[Xylopropamine]]||H||CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||H||H||H||[[File:Xylopropamine.svg|170px]]
|-
|-
| [[Clobenzorex]] || ''N''-(2-chlorobenzyl)-1-phenylpropan-2-amine || 1 |
|[[β-methylamphetamine]]||H||H||H||H||H||H||CH<sub>3</sub>||H||H||[[File:β-methylamphetamine.svg|170px]]
|-
|-
| [[Dimethylamphetamine]] || ''N'',''N''-Dimethylamphetamine || 2 |
|[[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]]
|-
|-
| [[Benzphetamine]] || ''N''-Benzyl-''N''-methylamphetamine || 2 |
|[[2-FA]]||F||H||H||H||H||H||H||H||H||[[File:2-FA.svg|170px]]
|-
|-
| [[Selegiline]] || ''N''-Methyl-''N''-propargylamphetamine, (''R'')- || 2 |
|[[2-FMA]]||F||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:2-FMA.svg|170px]]
|-
|-
| [[Mephentermine]] || ''N''-Methyl-α-methylamphetamine || 2 |
|[[2-FEA]]||F||H||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:2-FEA.svg|170px]]
|-
|-
| [[Phenpentermine]] || α,β-Dimethylamphetamine || 2 |
|[[3-FA]]||H||F||H||H||H||H||H||H||H||[[File:3-FA.svg|170px]]
|-
|-
| [[Ephedrine]] || β-Hydroxy-''N''-methylamphetamine, (1''R'',2''S'')- || 2 |
|[[3-FMA]]||H||F||H||H||H||H||H||H||CH<sub>3</sub>||[[File:3-FMA.svg|170px]]
|-
|-
| [[Pseudoephedrine]] (PSE) || β-Hydroxy-''N''-methylamphetamine, (1''S'',2''S'')- || 2 |
|[[3-FEA]]||H||F||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:3-FEA.svg|170px]]
|-
|-
| [[Methcathinone]] || β-Keto-''N''-methylamphetamine || 2 |
|[[Fenfluramine]]||H||CF<sub>3</sub>||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:Fenfluramine.svg|170px]]
|-
|-
| [[Ethcathinone]] || β-Keto-''N''-ethylamphetamine || 2 |
|[[Norfenfluramine]]||H||CF<sub>3</sub>||H||H||H||H||H||H||H||[[File:Norfenfluramine.svg|170px]]
|-
|-
| [[Clortermine]] || 2-Chloro-α-methylamphetamine || 2 |
|[[4-FA]]||H||H||F||H||H||H||H||H||H||[[File:4-FA.svg|170px]]
|-
|-
| [[Methoxymethylamphetamine]] (MMA) || 3-Methoxy-4-methylamphetamine || 2 |
|[[4-FMA]]||H||H||F||H||H||H||H||H||CH<sub>3</sub>||[[File:4-FMA.svg|170px]]
|-
|-
| [[Fenfluramine]] || 3-Trifluoromethyl-''N''-ethylamphetamine || 2 |
|[[3-CMA]]||H||H||H||Cl||H||H||H||H||H||[[File:3-CMA.svg|170px]]
|-
|-
| [[Dexfenfluramine]] || 3-Trifluoromethyl-''N''-ethylamphetamine, (''S'')- || 2 |
|[[4-CA]]||H||H||Cl||H||H||H||H||H||H||[[File:4-CA.svg|170px]]
|-
|-
| [[4-Methylmethamphetamine]] (4-MMA) || 4-Methyl-''N''-methylamphetamine || 2 |
|[[4-BA]]||H||H||Br||H||H||H||H||H||H||[[File:4-BA.svg|170px]]
|-
|-
| [[Para-methoxymethamphetamine]] (PMMA) || 4-Methoxy-''N''-methylamphetamine || 2 |
|[[4-IA]]||H||H||I||H||H||H||H||H||H||[[File:4-IA.svg|170px]]
|-
|-
| [[para-Methoxyethylamphetamine|''para''-Methoxyethylamphetamine]] (PMEA) || 4-Methoxy-''N''-ethylamphetamine || 2 |
|[[DCA]]||H||Cl||Cl||H||H||H||H||H||H||[[File:DCA.svg|170px]]
|-
|-
| [[Pholedrine]] || 4-Hydroxy-''N''-methylamphetamine || 2 |
|[[4-HA]]||H||H||OH||H||H||H||H||H||H||[[File:4-HA.svg|170px]]
|-
|-
| [[Chlorphentermine]] || 4-Chloro-α-methylamphetamine || 2 |
|[[4-HMA]]||H||H||OH||H||H||H||H||H||CH<sub>3</sub>||[[File:4-HMA.svg|170px]]
|-
|-
| [[para-Fluoromethamphetamine|''para''-Fluoromethamphetamine]] (PFMA, 4-FMA) || 4-Fluoro-''N''-methylamphetamine || 2 |
|[[3,4-DHA]]||H||OH||OH||H||H||H||H||H||H||[[File:3,4-DHA.svg|170px]]
|-
|-
| [[Xylopropamine]] || 3,4-Dimethylamphetamine || 2 |
|[[OMA]]||OCH<sub>3</sub>||H||H||H||H||H||H||H||H||[[File:OMA.svg|170px]]
|-
|-
| [[α-Methyldopamine]] (α-Me-DA) || 3,4-Dihydroxyamphetamine || 2 |
|[[3-MA]]||H||OCH<sub>3</sub>||H||H||H||H||H||H||H||[[File:3-MA.svg|170px]]
|-
|-
| [[Methylenedioxyamphetamine]] (MDA) || 3,4-Methylenedioxyamphetamine || 2 |
|[[MMMA]]||H||OCH<sub>3</sub>||H||H||H||H||H||H||CH<sub>3</sub>||[[File:MMMA.svg|170px]]
|-
|-
| [[Dimethoxyamphetamine]] (DMA) || X,X-Dimethoxyamphetamine || 2 |
|[[MMA]]||H||OCH<sub>3</sub>||CH<sub>3</sub>||H||H||H||H||H||H||[[File:MMA.svg|170px]]
|-
|-
| [[Nordefrin]] (α-Me-NE) || β,3,4-Trihydroxyamphetamine, (''R'')- || 3 |
|[[PMA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||H||[[File:PMA.svg|171px]]
|-
|-
| [[Oxilofrine]] || β,4-Dihydroxy-''N''-methylamphetamine || 3 |
|[[PMMA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||CH<sub>3</sub>||[[File:PMMA.svg|171px]]
|-
|-
| [[Aleph (psychedelic)|Aleph]] || 2,5-dimethoxy-4-methylthioamphetamine || 3 |
|[[PMEA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:PMEA.svg|170px]]
|-
|-
| [[Dimethoxybromoamphetamine]] (DOB) || 2,5-Dimethoxy-4-bromoamphetamine || 3 |
|[[4-ETA]]||H||H||OCH<sub>2</sub>CH<sub>3</sub>||H||H||H||H||H||H||[[File:4-ETA.svg|170px]]
|-
|-
| [[Dimethoxychloroamphetamine]] (DOC) || 2,5-Dimethoxy-4-chloroamphetamine || 3 |
|[[TMA]]||H||OCH<sub>3</sub>||OCH<sub>3</sub>||OCH<sub>3</sub>||H||H||H||H||H||[[File:TMA-1.svg|170px]]
|-
|-
| [[Dimethoxyfluoroethylamphetamine]] (DOEF) || 2,5-Dimethoxy-4-fluoroethylamphetamine || 3 |
|[[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]]
|-
|-
| [[Dimethoxyethylamphetamine]] (DOET) || 2,5-Dimethoxy-4-ethylamphetamine || 3 |
|[[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]]
|-
|-
| [[Dimethoxyfluoroamphetamine]] (DOF) || 2,5-Dimethoxy-4-fluoroamphetamine || 3 |
|[[4-MTA]]||H||H||SCH<sub>3</sub>||H||H||H||H||H||H||[[File:4-MTA.svg|170px]]
|-
|-
| [[Dimethoxyiodoamphetamine]] (DOI) || 2,5-Dimethoxy-4-iodoamphetamine || 3 |
|[[5-API]]||H||CH=CH-||NH-||H||H||H||H||H||H||[[File:5-API.svg|170px]]
|-
|-
| [[Dimethoxymethylamphetamine]] (DOM) || 2,5-Dimethoxy-4-methylamphetamine || 3 |
|[[Cathine]]||H||H||H||H||H||H||OH||H||H||[[File:Cathine.svg|170px]]
|-
|-
| [[Dimethoxynitroamphetamine]] (DON) || 2,5-Dimethoxy-4-nitroamphetamine || 3 |
|[[Pseudoephedrine]]||H||H||H||H||H||H||OH||H||CH<sub>3</sub>||[[File:Pseudoephedrine.svg|170px]]
|-
|-
| [[Dimethoxypropylamphetamine]] (DOPR) || 2,5-Dimethoxy-4-propylamphetamine || 3 |
|[[Phenmetrazine]]||H||H||H||H||H||H||OCH<sub>2</sub>-||CH<sub>2</sub>-||H||[[File:Phenmetrazine.svg|170px]]
|-
|-
| [[Dimethoxytrifluoromethylamphetamine]] (DOTFM) || 2,5-Dimethoxy-4-trifluoromethylamphetamine || 3 |
|[[3-FPM]]||H||F||H||H||H||H||OCH<sub>2</sub>-||CH<sub>2</sub>-||H||[[File:3-FPM.svg|170px]]
|-
|-
| Methylenedioxymethamphetamine ([[MDMA]]) || 3,4-Methylenedioxy-''N''-methylamphetamine || 3 |
|[[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]]
|-
|-
| [[Methylenedioxyethylamphetamine]] (MDEA) || 3,4-Methylenedioxy-''N''-ethylamphetamine || 3 |
|[[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]]
|-
| [[Methylenedioxyhydroxyamphetamine]] (MDOH) || 3,4-Methylenedioxy-''N''-hydroxyamphetamine || 3 |
|-
| [[2-Methyl-MDA]] || 3,4-Methylenedioxy-2-methylamphetamine || 3 |
|-
| [[5-Methyl-MDA]] || 4,5-Methylenedioxy-3-methylamphetamine || 3 |
|-
| [[Methoxymethylenedioxyamphetamine]] (MMDA) || 3-Methoxy-4,5-methylenedioxyamphetamine || 3 |
|-
| [[Trimethoxyamphetamine]] (TMA) || X,X,X-Trimethoxyamphetamine || 3 |
|-
| [[Dimethylcathinone]] || β-Keto-''N'',''N''-dimethylamphetamine || 3 |
|-
| [[Diethylcathinone]] || β-Keto-''N'',''N''-diethylamphetamine || 3 |
|-
| [[Bupropion]] || β-Keto-3-chloro-''N''-''tert''-butylamphetamine || 3 |
|-
| [[Mephedrone]] (4-MMC) || β-Keto-4-methyl-''N''-methylamphetamine || 3 |
|-
| [[Methedrone]] (PMMC) || β-Keto-4-methoxy-''N''-methylamphetamine || 3 |
|-
| [[Brephedrone]] (4-BMC) || β-Keto-4-bromo-''N''-methylamphetamine || 3 |
|-
| [[Flephedrone]] (4-FMC) || β-Keto-4-fluoro-''N''-methylamphetamine || 3 |
|-
|-
|}
|}


==See also==
==See also==
*[[Psychedelics]]
 
*[[Phenethylamines]]
*[[Responsible use]]
*[[Entactogens]]
*[[Phenethylamine]]
*[[Stimulants]]
*[[Stimulants]]
*[[Entactogen]]
*[[Psychedelic]]
==External links==
*[[wikipedia:Substituted amphetamine|Substituted amphetamine (Wikipedia)]]


==References==
==References==
{{references}}
{{references}}
[[Category:Chemical class]]
[[Category:Amphetamine|*]]
{{#set:Featured=true}}
Retrieved from "http://psy.st/wiki/Substituted_amphetamines"