Substituted amphetamines: Difference between revisions

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[[File:samphetamine.png|thumb|right|301px||Generic structure of an amphetamine molecule]]
[[File:Substituted_amphetamine.svg|thumb|right|301px||Substitutive structure of an ''amphetamine'' molecule.]]
'''Substituted amphetamines''' are a family of modified [[amphetamine]] molecules that include compounds with psychoactive effects, which typically have classical [[stimulant]] but may also include [[entactogen]]ic (e.g. [[MDA]] and [[MDMA]]) and [[psychedelic]] effects (e.g. [[DOx]] or [[TMA-6]]).
'''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==
[[File:Phenethylamine.png|thumb|right|245px|Generic structure of a ''phenethylamine'' molecule]]
[[File:Substituted_phenethylamine.svg|thumb|right|245px|Substitutive structure of a ''phenethylamine'' molecule.]]


Substituted amphetamines are a class of chemicals that have structures based on the molecular backbone of [[amphetamine]] with different substitutions at varying positions. Of note, 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 only unsubstituted member of the substituted amphetamine class, amphetamine can also considered ton be a [[Substituted Phenethylamines|substituted phenethylamine]].
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}}


== List of substituted amphetamines ==
==List of substituted amphetamines==
''Note: This list does not include [[Substituted Phenethylamine|phenethylamines]], [[Substituted 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:Amphetamine2.png|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:Meth.png|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>3</sub> || [[File:Ethylamphetamine.png|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.png|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.png|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.png|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:Lisdexamphetamine.png|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.png|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.png|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.png|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.png|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.png|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.png|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-MMA.png|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.png|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:Beta-methylamphetamine.png|170px]]
|[[4-Methylamphetamine]]||H||H||CH<sub>3</sub>||H||H||H||H||H||H||[[File:4-Methylamphetamine.svg|170px]]
|-
|-
| [[2-FA]] || F || H || H || H || H || H || H || H || H || [[File:2-FA.png|170px]]
|[[3-MMA]]||H||CHз||H||H||H||H||H||H||CHз||[[File:3-Methylmethamphetamine.svg|170px]]
|-
|-
| [[2-FMA]] || F || H || H || H || H || H || H || H || CH<sub>3</sub> || [[File:2fluoromethamphetamine.png|170px]]
|[[4-MMA]]||H||H||CH<sub>3</sub>||H||H||H||H||H||CH<sub>3</sub>||[[File:4-Methylmethamphetamine.svg|170px]]
|-
|-
| 3-FA || H || F || H || H || H || H || H || H || H || [[File:3-FA.png|170px]]
|[[Xylopropamine]]||H||CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||H||H||H||[[File:Xylopropamine.svg|170px]]
|-
|-
| 3-FMA || H || F || H || H || H || H || H || H || CH<sub>3</sub> || [[File:3-FMA.png|170px]]
|[[β-methylamphetamine]]||H||H||H||H||H||H||CH<sub>3</sub>||H||H||[[File:β-methylamphetamine.svg|170px]]
|-
|-
| [[3-FEA]] || H || F || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:3-FEA.png|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]]
|-
|-
| [[4-FA]] || H || H || F || H || H || H || H || H || H || [[File:4fa.png|170px]]
|[[2-FA]]||F||H||H||H||H||H||H||H||H||[[File:2-FA.svg|170px]]
|-
|-
| 4-FMA || H || H || F || H || H || H || H || H || CH<sub>3</sub> || [[File:4-FMA.png|170px]]
|[[2-FMA]]||F||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:2-FMA.svg|170px]]
|-
|-
| 4-CA || H || H || Cl || H || H || H || H || H || H || [[File:4-CA.png|170px]]
|[[2-FEA]]||F||H||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:2-FEA.svg|170px]]
|-
|-
| 4-BA || H || H || Br || H || H || H || H || H || H || [[File:4-BA.png|170px]]
|[[3-FA]]||H||F||H||H||H||H||H||H||H||[[File:3-FA.svg|170px]]
|-
|-
| 4-IA || H || H || I || H || H || H || H || H || H || [[File:4-IA.png|170px]]
|[[3-FMA]]||H||F||H||H||H||H||H||H||CH<sub>3</sub>||[[File:3-FMA.svg|170px]]
|-
|-
| DCA || H || Cl || Cl || H || H || H || H || H || H || [[File:DCA.png|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-HA || H || H || OH || H || H || H || H || H || H || [[File:4-HA.png|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-HMA || H || H || OH || H || H || H || H || H || CH<sub>3</sub> || [[File:4-HMA.png|170px]]
|[[Norfenfluramine]]||H||CF<sub>3</sub>||H||H||H||H||H||H||H||[[File:Norfenfluramine.svg|170px]]
|-
|-
| 3,4-DHA || H || OH || OH || H || H || H || H || H || H || [[File:3,4-DHA.png|170px]]
|[[4-FA]]||H||H||F||H||H||H||H||H||H||[[File:4-FA.svg|170px]]
|-
|-
| OMA || OCH<sub>3</sub> || H || H || H || H || H || H || H || H || [[File:OMA.png|170px]]
|[[4-FMA]]||H||H||F||H||H||H||H||H||CH<sub>3</sub>||[[File:4-FMA.svg|170px]]
|-
|-
| 3-MA || H || OCH<sub>3</sub> || H || H || H || H || H || H || H || [[File:3-MA.png|170px]]
|[[3-CMA]]||H||H||H||Cl||H||H||H||H||H||[[File:3-CMA.svg|170px]]
|-
|-
| MMMA || H || OCH<sub>3</sub> || H || H || H || H || H || H || CH<sub>3</sub> || [[File:MMMA.png|170px]]
|[[4-CA]]||H||H||Cl||H||H||H||H||H||H||[[File:4-CA.svg|170px]]
|-
|-
| MMA || H || OCH<sub>3</sub> || CH<sub>3</sub> || H || H || H || H || H || H || [[File:MMA.png|170px]]
|[[4-BA]]||H||H||Br||H||H||H||H||H||H||[[File:4-BA.svg|170px]]
|-
|-
| [[PMA]] || H || H || OCH<sub>3</sub> || H || H || H || H || H || H || [[File:PMA.png|171px]]
|[[4-IA]]||H||H||I||H||H||H||H||H||H||[[File:4-IA.svg|170px]]
|-
|-
| [[PMMA]] || H || H || OCH<sub>3</sub> || H || H || H || H || H || CH<sub>3</sub> || [[File:PMMA.png|171px]]
|[[DCA]]||H||Cl||Cl||H||H||H||H||H||H||[[File:DCA.svg|170px]]
|-
|-
| PMEA || H || H || OCH<sub>3</sub> || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:PMEA.png|170px]]
|[[4-HA]]||H||H||OH||H||H||H||H||H||H||[[File:4-HA.svg|170px]]
|-
|-
| 4-ETA || H || H || OCH<sub>2</sub>CH<sub>3</sub> || H || H || H || H || H || H || [[File:4-ETA.png|170px]]
|[[4-HMA]]||H||H||OH||H||H||H||H||H||CH<sub>3</sub>||[[File:4-HMA.svg|170px]]
|-
|-
| 4-MTA || H || H || SCH<sub>3</sub> || H || H || H || H || H || H || [[File:4-MTA.png|170px]]
|[[3,4-DHA]]||H||OH||OH||H||H||H||H||H||H||[[File:3,4-DHA.svg|170px]]
|-
|-
| Cathine || H || H || H || H || H || H || OH || H || H || [[File:Cathine.png|170px]]
|[[OMA]]||OCH<sub>3</sub>||H||H||H||H||H||H||H||H||[[File:OMA.svg|170px]]
|-
|[[3-MA]]||H||OCH<sub>3</sub>||H||H||H||H||H||H||H||[[File:3-MA.svg|170px]]
|-
|[[MMMA]]||H||OCH<sub>3</sub>||H||H||H||H||H||H||CH<sub>3</sub>||[[File:MMMA.svg|170px]]
|-
|[[MMA]]||H||OCH<sub>3</sub>||CH<sub>3</sub>||H||H||H||H||H||H||[[File:MMA.svg|170px]]
|-
|[[PMA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||H||[[File:PMA.svg|171px]]
|-
|[[PMMA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||CH<sub>3</sub>||[[File:PMMA.svg|171px]]
|-
|[[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==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Psychedelics]]
*[[Phenethylamine]]
*[[Phenethylamines]]
*[[Entactogens]]
*[[Stimulants]]
*[[Stimulants]]
*[[Entactogen]]
*[[Psychedelic]]
==External links==
*[[wikipedia:Substituted amphetamine|Substituted amphetamine (Wikipedia)]]


==References==
==References==
{{references}}
{{references}}
[[Category:Chemical class]]
[[Category:Amphetamine|*]]
{{#set:Featured=true}}