
Substituted amphetamines: Difference between revisions
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[[File:Substituted_amphetamine.svg|thumb|right|301px||Substitutive structure of an ''amphetamine'' molecule.]] | [[File:Substituted_amphetamine.svg|thumb|right|301px||Substitutive structure of an ''amphetamine'' molecule.]] | ||
'''Substituted amphetamines''' | '''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== | ||
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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-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}} | 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]], [[ | ''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]] | ||
|- | |- | ||
| | |[[Dextromethamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Dextromethamphetamine.svg|170px]] | ||
|- | |- | ||
| | |[[Levomethamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Levomethamphetamine.svg|170px]] | ||
|- | |- | ||
| | |[[Ethylamphetamine]] (''Etilamfetamine'')||H||H||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:Ethylamphetamine.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]] | ||
|- | |- | ||
| [[ | |[[Isopropylamphetamine]]||H||H||H||H||H||H||H||H||CH(CH<sub>3</sub>)<sub>2</sub>||[[File:Isopropylamphetamine.svg|170px]] | ||
|- | |- | ||
| | |[[Bromo-DragonFLY]]||OCH=CH-||-||Br||OCH=CH-||-||H||H||H||H||[[File:Bromo-DragonFLY.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]] | ||
|- | |- | ||
| | |[[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]] | ||
|- | |- | ||
| | |[[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]] | ||
|- | |- | ||
| | |[[Dimethylamphetamine]]||H||H||H||H||H||H||H||CH<sub>3</sub>||CH<sub>3</sub>||[[File:Dimethylamphetamine.svg|170px]] | ||
|- | |- | ||
| | |[[Selegiline]]||H||H||H||H||H||H||H||CH<sub>3</sub>||CH<sub>2</sub>CCH||[[File:Selegiline.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]] | ||
|- | |- | ||
| | |[[Ortetamine]]||CH<sub>3</sub>||H||H||H||H||H||H||H||H||[[File:Ortetamine.svg|170px]] | ||
|- | |- | ||
| | |[[3-Methylamphetamine]]||H||CH<sub>3</sub>||H||H||H||H||H||H||H||[[File:3-Methylamphetamine.svg|170px]] | ||
|- | |- | ||
| | |[[4-Methylamphetamine]]||H||H||CH<sub>3</sub>||H||H||H||H||H||H||[[File:4-Methylamphetamine.svg|170px]] | ||
|- | |- | ||
| | |[[3-MMA]]||H||CHз||H||H||H||H||H||H||CHз||[[File:3-Methylmethamphetamine.svg|170px]] | ||
|- | |- | ||
| [[ | |[[4-MMA]]||H||H||CH<sub>3</sub>||H||H||H||H||H||CH<sub>3</sub>||[[File:4-Methylmethamphetamine.svg|170px]] | ||
|- | |- | ||
| [[ | |[[Xylopropamine]]||H||CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||H||H||H||[[File:Xylopropamine.svg|170px]] | ||
|- | |- | ||
| [[ | |[[β-methylamphetamine]]||H||H||H||H||H||H||CH<sub>3</sub>||H||H||[[File:β-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]] | ||
|- | |- | ||
| [[ | |[[2-FA]]||F||H||H||H||H||H||H||H||H||[[File:2-FA.svg|170px]] | ||
|- | |- | ||
| [[ | |[[2-FMA]]||F||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:2-FMA.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]] | ||
|- | |- | ||
| | |[[3-FA]]||H||F||H||H||H||H||H||H||H||[[File:3-FA.svg|170px]] | ||
|- | |- | ||
| [[ | |[[3-FMA]]||H||F||H||H||H||H||H||H||CH<sub>3</sub>||[[File:3-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]] | ||
|- | |- | ||
| | |[[Fenfluramine]]||H||CF<sub>3</sub>||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:Fenfluramine.svg|170px]] | ||
|- | |- | ||
| | |[[Norfenfluramine]]||H||CF<sub>3</sub>||H||H||H||H||H||H||H||[[File:Norfenfluramine.svg|170px]] | ||
|- | |- | ||
| 4- | |[[4-FA]]||H||H||F||H||H||H||H||H||H||[[File:4-FA.svg|170px]] | ||
|- | |- | ||
| | |[[4-FMA]]||H||H||F||H||H||H||H||H||CH<sub>3</sub>||[[File:4-FMA.svg|170px]] | ||
|- | |- | ||
| | |[[3-CMA]]||H||H||H||Cl||H||H||H||H||H||[[File:3-CMA.svg|170px]] | ||
|- | |- | ||
| 4- | |[[4-CA]]||H||H||Cl||H||H||H||H||H||H||[[File:4-CA.svg|170px]] | ||
|- | |- | ||
| | |[[4-BA]]||H||H||Br||H||H||H||H||H||H||[[File:4-BA.svg|170px]] | ||
|- | |- | ||
| | |[[4-IA]]||H||H||I||H||H||H||H||H||H||[[File:4-IA.svg|170px]] | ||
|- | |- | ||
| | |[[DCA]]||H||Cl||Cl||H||H||H||H||H||H||[[File:DCA.svg|170px]] | ||
|- | |- | ||
| | |[[4-HA]]||H||H||OH||H||H||H||H||H||H||[[File:4-HA.svg|170px]] | ||
|- | |- | ||
| | |[[4-HMA]]||H||H||OH||H||H||H||H||H||CH<sub>3</sub>||[[File:4-HMA.svg|170px]] | ||
|- | |- | ||
| [[ | |[[3,4-DHA]]||H||OH||OH||H||H||H||H||H||H||[[File:3,4-DHA.svg|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]] | ||
|- | |- | ||
| 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== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Phenethylamine]] | *[[Phenethylamine]] | ||
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==External links== | ==External links== | ||
*[[wikipedia:Substituted amphetamine|Substituted amphetamine (Wikipedia)]] | *[[wikipedia:Substituted amphetamine|Substituted amphetamine (Wikipedia)]] | ||
==References== | ==References== | ||
{{references}} | {{references}} | ||
[[Category:Chemical class]] | |||
[[Category:Amphetamine|*]] | |||
{{#set:Featured=true}} |
Latest revision as of 17:05, 15 February 2025
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
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 substituted phenethylamine.
Pharmacology
Psychoactive substances of the substituted amphetamine class typically produce effects through dopaminergic, serotonergic, and adrenergic pathways. Psychedelic effects can be attributed to action on the 5-HT2A receptor.[citation needed] Stimulant and entactogenic effects are due to their action as releasing agents of dopamine, serotonin, epinephrine and norepinephrine or as 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 cognitive and physical stimulation within the user.[citation needed]
List of substituted amphetamines
Note: This list does not include phenidates, cathinones, pyrrolidinophenones MDxxs, DOxs, benzofurans among other further substituted amphetamines.
Compound | R2 | R3 | R4 | R5 | R6 | Rα | Rβ | RN1 | RN2 | Structure |
---|---|---|---|---|---|---|---|---|---|---|
Amphetamine | H | H | H | H | H | H | H | H | H | |
Methamphetamine | H | H | H | H | H | H | H | H | CH3 | |
Dextromethamphetamine | H | H | H | H | H | H | H | H | CH3 | |
Levomethamphetamine | H | H | H | H | H | H | H | H | CH3 | |
Ethylamphetamine (Etilamfetamine) | H | H | H | H | H | H | H | H | CH2CH3 | |
Propylamphetamine | H | H | H | H | H | H | H | H | CH2CH2CH3 | |
Isopropylamphetamine | H | H | H | H | H | H | H | H | CH(CH3)2 | |
Bromo-DragonFLY | OCH=CH- | - | Br | OCH=CH- | - | H | H | H | H | |
Lisdexamfetamine | H | H | H | H | H | H | H | H | COCH(NH2)(CH2)4NH2 | |
Fenethylline | H | H | H | H | H | H | H | H | C9H12N4O2 | |
Clobenzorex | H | H | H | H | H | H | H | H | CH2C6H4Cl | |
Dimethylamphetamine | H | H | H | H | H | H | H | CH3 | CH3 | |
Selegiline | H | H | H | H | H | H | H | CH3 | CH2CCH | |
Benzphetamine | H | H | H | H | H | H | H | CH3 | CH2C6H5 | |
Ortetamine | CH3 | H | H | H | H | H | H | H | H | |
3-Methylamphetamine | H | CH3 | H | H | H | H | H | H | H | |
4-Methylamphetamine | H | H | CH3 | H | H | H | H | H | H | |
3-MMA | H | CHз | H | H | H | H | H | H | CHз | |
4-MMA | H | H | CH3 | H | H | H | H | H | CH3 | |
Xylopropamine | H | CH3 | CH3 | H | H | H | H | H | H | |
β-methylamphetamine | H | H | H | H | H | H | CH3 | H | H | |
β-phenylmethamphetamine | H | H | H | H | H | H | C6H5 | H | CH3 | |
2-FA | F | H | H | H | H | H | H | H | H | |
2-FMA | F | H | H | H | H | H | H | H | CH3 | |
2-FEA | F | H | H | H | H | H | H | H | CH2CH3 | |
3-FA | H | F | H | H | H | H | H | H | H | |
3-FMA | H | F | H | H | H | H | H | H | CH3 | |
3-FEA | H | F | H | H | H | H | H | H | CH2CH3 | |
Fenfluramine | H | CF3 | H | H | H | H | H | H | CH2CH3 | |
Norfenfluramine | H | CF3 | H | H | H | H | H | H | H | |
4-FA | H | H | F | H | H | H | H | H | H | |
4-FMA | H | H | F | H | H | H | H | H | CH3 | |
3-CMA | H | H | H | Cl | H | H | H | H | H | |
4-CA | H | H | Cl | H | H | H | H | H | H | |
4-BA | H | H | Br | H | H | H | H | H | H | |
4-IA | H | H | I | H | H | H | H | H | H | |
DCA | H | Cl | Cl | H | H | H | H | H | H | |
4-HA | H | H | OH | H | H | H | H | H | H | |
4-HMA | H | H | OH | H | H | H | H | H | CH3 | |
3,4-DHA | H | OH | OH | H | H | H | H | H | H | |
OMA | OCH3 | H | H | H | H | H | H | H | H | |
3-MA | H | OCH3 | H | H | H | H | H | H | H | |
MMMA | H | OCH3 | H | H | H | H | H | H | CH3 | |
MMA | H | OCH3 | CH3 | H | H | H | H | H | H | |
PMA | H | H | OCH3 | H | H | H | H | H | H | |
PMMA | H | H | OCH3 | H | H | H | H | H | CH3 | |
PMEA | H | H | OCH3 | H | H | H | H | H | CH2CH3 | |
4-ETA | H | H | OCH2CH3 | H | H | H | H | H | H | |
TMA | H | OCH3 | OCH3 | OCH3 | H | H | H | H | H | |
TMA-2 | OCH3 | H | OCH3 | OCH3 | H | H | H | H | H | |
TMA-6 | OCH3 | H | OCH3 | H | OCH3 | H | H | H | H | |
4-MTA | H | H | SCH3 | H | H | H | H | H | H | |
5-API | H | CH=CH- | NH- | H | H | H | H | H | H | |
Cathine | H | H | H | H | H | H | OH | H | H | |
Pseudoephedrine | H | H | H | H | H | H | OH | H | CH3 | |
Phenmetrazine | H | H | H | H | H | H | OCH2- | CH2- | H | |
3-FPM | H | F | H | H | H | H | OCH2- | CH2- | H | |
PPAP | H | H | H | H | H | CH2CH3 | H | H | CH2CH2CH3 | |
Prolintane | H | H | H | H | H | CH2CH3 | H | CH2CH2- | CH2CH2- |
See also
External links
References
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