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Substituted amphetamines: Difference between revisions
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>BronzeManul m Updated methamphetamine skeletal structure image in substituted amphetamines list. |
>BronzeManul Replaced skeletal structure images with standardised svg images. |
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! scope="col" | '''Structure''' | ! scope="col" | '''Structure''' | ||
|- | |- | ||
| [[Amphetamine]] || H || H || H || H || H || H || H || H || H || [[File: | | [[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. | | [[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. | | Ethylamphetamine (''Etilamfetamine'') || H || H || H || H || H || H || H || H || 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. | | 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. | | 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. | | [[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]] || 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]] | ||
|- | |- | ||
| Clobenzorex || H || H || H || H || H || H || H || H || CH<sub>2</sub>C<sub>6</sub>H<sub>4</sub>Cl || [[File:Clobenzorex. | | 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. | | 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. | | 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]] | | 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. | | 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. | | 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. | | 4-Methylamphetamine || H || H || CH<sub>3</sub> || H || H || H || H || H || H || [[File:4-Methylamphetamine.svg|170px]] | ||
|- | |- | ||
| 4-MMA || H || H || CH<sub>3</sub> || H || H || H || H || H || CH<sub>3</sub> || [[File:4- | | 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. | | 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 || 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 || 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. | | [[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]] || F || H || H || H || H || H || H || H || CH<sub>3</sub> || [[File:2-FMA.svg|170px]] | ||
|- | |- | ||
| [[3-FA]] || H || F || H || H || H || H || H || H || H || [[File:3-FA. | | [[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. | | [[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. | | [[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. | | 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. | | 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]] || 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. | | [[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. | | 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. | | 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. | | 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. | | 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. | | 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. | | 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. | | 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. | | 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. | | 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. | | 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. | | 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. | | [[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. | | [[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. | | 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. | | 4-ETA || H || H || OCH<sub>2</sub>CH<sub>3</sub> || H || H || H || H || H || H || [[File:4-ETA.svg|170px]] | ||
|- | |- | ||
| 4-MTA || H || H || SCH<sub>3</sub> || H || H || H || H || H || H || [[File:4-MTA. | | 4-MTA || H || H || SCH<sub>3</sub> || H || H || H || H || H || H || [[File:4-MTA.svg|170px]] | ||
|- | |- | ||
| Cathine || H || H || H || H || H || H || OH || H || H || [[File:Cathine. | | Cathine || H || H || H || H || H || H || OH || H || H || [[File:Cathine.svg|170px]] | ||
|- | |- | ||
|} | |} | ||
Revision as of 04:57, 30 August 2017
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 substances, which typically produce stimulant effects, entactogenic effects, and/or psychedelic effects.
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, MDxxs, DOxs, Benzofurans, or aminoindanes.
| 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 | 
|
| Ethylamphetamine (Etilamfetamine) | H | H | H | H | H | H | H | H | CH3 | 
|
| 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 | 
|
| 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 | 
|
| 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 | 
|
| 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 | 
|
| 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 | 
|
| 4-MTA | H | H | SCH3 | H | H | H | H | H | H | 
|
| Cathine | H | H | H | H | H | H | OH | H | H | 
|
See also
References
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