Substituted amphetamine

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Substitutive structure of an amphetamine molecule.

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

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, 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 Amphetamine.svg
Methamphetamine H H H H H H H H CH3 Methamphetamine.svg
Ethylamphetamine (Etilamfetamine) H H H H H H H H CH3 Ethylamphetamine.svg
Propylamphetamine H H H H H H H H CH2CH2CH3 Propylamphetamine.svg
Isopropylamphetamine H H H H H H H H CH(CH3)2 Isopropylamphetamine.svg
Bromo-DragonFLY OCH=CH- - Br OCH=CH- - H H H H Bromo-DragonFLY.svg
Lisdexamfetamine H H H H H H H H COCH(NH2)(CH2)4NH2 Lisdexamfetamine.svg
Clobenzorex H H H H H H H H CH2C6H4Cl Clobenzorex.svg
Dimethylamphetamine H H H H H H H CH3 CH3 Dimethylamphetamine.svg
Selegiline H H H H H H H CH3 CH2CCH Selegiline.svg
Benzphetamine H H H H H H H CH3 CH2C6H5 Benzphetamine.svg
Ortetamine CH3 H H H H H H H H Ortetamine.svg
3-Methylamphetamine H CH3 H H H H H H H 3-Methylamphetamine.svg
4-Methylamphetamine H H CH3 H H H H H H 4-Methylamphetamine.svg
4-MMA H H CH3 H H H H H CH3 4-Methylmethamphetamine.svg
Xylopropamine H CH3 CH3 H H H H H H Xylopropamine.svg
β-methylamphetamine H H H H H H CH3 H H Β-methylamphetamine.svg
β-phenylmethamphetamine H H H H H H C6H5 H CH3 Β-phenylmethamphetamine.svg
2-FA F H H H H H H H H 2-FA.svg
2-FMA F H H H H H H H CH3 2-FMA.svg
3-FA H F H H H H H H H 3-FA.svg
3-FMA H F H H H H H H CH3 3-FMA.svg
3-FEA H F H H H H H H CH2CH3 3-FEA.svg
Fenfluramine H CF3 H H H H H H CH2CH3 Fenfluramine.svg
Norfenfluramine H CF3 H H H H H H H Norfenfluramine.svg
4-FA H H F H H H H H H 4-FA.svg
4-FMA H H F H H H H H CH3 4-FMA.svg
4-CA H H Cl H H H H H H 4-CA.svg
4-BA H H Br H H H H H H 4-BA.svg
4-IA H H I H H H H H H 4-IA.svg
DCA H Cl Cl H H H H H H DCA.svg
4-HA H H OH H H H H H H 4-HA.svg
4-HMA H H OH H H H H H CH3 4-HMA.svg
3,4-DHA H OH OH H H H H H H 3,4-DHA.svg
OMA OCH3 H H H H H H H H OMA.svg
3-MA H OCH3 H H H H H H H 3-MA.svg
MMMA H OCH3 H H H H H H CH3 MMMA.svg
MMA H OCH3 CH3 H H H H H H MMA.svg
PMA H H OCH3 H H H H H H PMA.svg
PMMA H H OCH3 H H H H H CH3 PMMA.svg
PMEA H H OCH3 H H H H H CH2CH3 PMEA.svg
4-ETA H H OCH2CH3 H H H H H H 4-ETA.svg
4-MTA H H SCH3 H H H H H H 4-MTA.svg
Cathine H H H H H H OH H H Cathine.svg

See also

References

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