Substituted amphetamines

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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  
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-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  
Phenmetrazine H H H H H H OCH2- CH2- H  
3-FPM H F H H H H OCH2- CH2- H  
Prolintane H H H H H CH2CH3 H CH2CH2- CH2CH2-  

See also

External links

References

 

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