Substituted amphetamines

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-HT_2A receptor. 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. 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.

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

• Responsible use
• Phenethylamine
• Stimulants
• Entactogen
• Psychedelic

External links

• Substituted amphetamine (Wikipedia)

References

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