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Substituted amphetamines: Difference between revisions
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>Pharmreduction m Added TMA-2 |
>Tracer Added structures |
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==List of substituted amphetamines== | ==List of substituted amphetamines== | ||
''Note: This list does not include [[Phenidate|phenidates]], [[Substituted cathinone|cathinones]], [[MDxx|MDxxs]], [[DOx|DOxs]], [[benzofurans]] | ''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 mw-collapsible" | ||
|- | |- | ||
| Line 30: | Line 30: | ||
|[[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]] | ||
|- | |- | ||
|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]] | ||
|- | |||
|[[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]] | |[[Bromo-DragonFLY]]||OCH=CH-||-||Br||OCH=CH-||-||H||H||H||H||[[File:Bromo-DragonFLY.svg|170px]] | ||
| Line 40: | Line 44: | ||
|[[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]] | |[[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- | |[[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]] | ||
|- | |- | ||
|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]] | |[[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-FA]]||F||H||H||H||H||H||H||H||H||[[File:2-FA.svg|170px]] | ||
| Line 74: | Line 82: | ||
|[[3-FEA]]||H||F||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:3-FEA.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]] | |[[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]] | |[[Norfenfluramine]]||H||CF<sub>3</sub>||H||H||H||H||H||H||H||[[File:Norfenfluramine.svg|170px]] | ||
|- | |- | ||
|[[4-FA]]||H||H||F||H||H||H||H||H||H||[[File:4-FA.svg|170px]] | |[[4-FA]]||H||H||F||H||H||H||H||H||H||[[File:4-FA.svg|170px]] | ||
| Line 82: | Line 90: | ||
|[[4-FMA]]||H||H||F||H||H||H||H||H||CH<sub>3</sub>||[[File:4-FMA.svg|170px]] | |[[4-FMA]]||H||H||F||H||H||H||H||H||CH<sub>3</sub>||[[File:4-FMA.svg|170px]] | ||
|- | |- | ||
|4-CA||H||H||Cl||H||H||H||H||H||H||[[File:4-CA.svg|170px]] | |[[3-CMA]]||H||H||H||Cl||H||H||H||H||H||[[File:3-CMA.svg|170px]] | ||
|- | |||
|[[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-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]] | |[[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]] | |[[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-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]] | |[[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]] | |[[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]] | |[[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]] | |[[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]] | |[[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]] | |[[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]] | |[[PMA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||H||[[File:PMA.svg|171px]] | ||
| Line 108: | Line 118: | ||
|[[PMMA]]||H||H||OCH<sub>3</sub>||H||H||H||H||H||CH<sub>3</sub>||[[File:PMMA.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]] | |[[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-2]]||OCH<sub>3</sub>||H||OCH<sub>3</sub>||OCH<sub>3</sub>||H||H||H||H||H||[[File:TMA-2.svg|170px]] | ||
| Line 116: | Line 128: | ||
|[[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]] | |[[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]] | |[[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]] | ||
|- | |- | ||
|Phenmetrazine||H||H||H||H||H||H||OCH<sub>2</sub>-||CH<sub>2</sub>-||H||[[File:Phenmetrazine.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]] | |[[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]] | |[[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]] | ||
| Line 145: | Line 163: | ||
[[Category:Chemical class]] | [[Category:Chemical class]] | ||
[[Category:Amphetamine|*]] | [[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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