Substituted amphetamines

Substituted amphetamines are a family of modified amphetamine molecules that include compounds with psychoactive effects, which typically have classical stimulant but may also include entactogenic (e.g. MDA and MDMA) and psychedelic effects (e.g. DOx or TMA-6).

Generic structure of an amphetamine molecule

Chemistry

Generic structure of a phenethylamine molecule

Substituted amphetamines are a class of chemicals that have structures based on the molecular backbone of amphetamine with different substitutions at varying positions. Of note, 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 only unsubstituted member of the substituted amphetamine class, amphetamine can also considered ton be a substituted phenethylamine.

Pharmacology

The substituted amphetamine class of psychedelic, entactogenic and stimulant drugs works via their action upon numerous receptors. Psychedelic effects can be attributed to action on the 5-HT_2A receptor. Entactogenic and stimulant effects are due to their action as releasing agents of serotonin, adrenaline and noradrenaline 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 phenethylamines, 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
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
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

• Responsible use
• Psychedelics
• Phenethylamines
• Entactogens
• Stimulants

References

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