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Substituted amphetamines: Difference between revisions

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|[[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]]
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|[[Dextromethamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Dextromethamphetamine.svg|170px]]
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|[[Levomethamphetamine]]||H||H||H||H||H||H||H||H||CH<sub>3</sub>||[[File:Levomethamphetamine.svg|170px]]
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|[[Ethylamphetamine]] (''Etilamfetamine'')||H||H||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:Ethylamphetamine.svg|170px]]
|[[Ethylamphetamine]] (''Etilamfetamine'')||H||H||H||H||H||H||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:Ethylamphetamine.svg|170px]]
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|[[4-Methylamphetamine]]||H||H||CH<sub>3</sub>||H||H||H||H||H||H||[[File:4-Methylamphetamine.svg|170px]]
|[[4-Methylamphetamine]]||H||H||CH<sub>3</sub>||H||H||H||H||H||H||[[File:4-Methylamphetamine.svg|170px]]
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|3-MMA
|[[3-MMA]]||H||CHз||H||H||H||H||H||H||CHз||[[File:3-Methylmethamphetamine.svg|170px]]
|H
|CHз
|H
|H
|H
|H
|H
|H
|CHз
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|[[4-MMA|4-MMA]]|H||H||CH<sub>3</sub>||H||H||H||H||H||CH<sub>3</sub>||[[File:4-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]]
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|[[Xylopropamine]]||H||CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||H||H||H||[[File:Xylopropamine.svg|170px]]
|[[Xylopropamine]]||H||CH<sub>3</sub>||CH<sub>3</sub>||H||H||H||H||H||H||[[File:Xylopropamine.svg|170px]]
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|[[4-ETA]]||H||H||OCH<sub>2</sub>CH<sub>3</sub>||H||H||H||H||H||H||[[File:4-ETA.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]]
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|[[TMA]]||H||OCH<sub>3</sub>||OCH<sub>3</sub>||OCH<sub>3</sub>||H||H||H||H||H||[[File:TMA-1.svg|170px]]
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|[[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]]
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|[[Cathine]]||H||H||H||H||H||H||OH||H||H||[[File:Cathine.svg|170px]]
|[[Cathine]]||H||H||H||H||H||H||OH||H||H||[[File:Cathine.svg|170px]]
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|[[Pseudoephedrine]]||H||H||H||H||H||H||OH||H||CH<sub>3</sub>||[[File:Pseudoephedrine.svg|170px]]
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|[[Phenmetrazine]]||H||H||H||H||H||H||OCH<sub>2</sub>-||CH<sub>2</sub>-||H||[[File:Phenmetrazine.svg|170px]]
|[[Phenmetrazine]]||H||H||H||H||H||H||OCH<sub>2</sub>-||CH<sub>2</sub>-||H||[[File:Phenmetrazine.svg|170px]]
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|[[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]]
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|[[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]]
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|[[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]]

Latest revision as of 17:05, 15 February 2025

Substitutive structure of an amphetamine molecule.

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

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 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

References

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