Substituted amphetamines: Difference between revisions

[[File:samphetamine.png|thumb|right|301px||Generic structure of an amphetamine molecule]]

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

Substituted amphetamines are a chemical class based upon the molecule [[amphetamine]]. Amphetamine is made up of a [[Substituted Phenethylamines|phenethylamine]] molecule. The chemical structure of a substituted amphetamine is the same as the organic molecule amphetamine, except some substitutions are made at the phenyl and amine sites, typically of methyl and ethyl chains.

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 [[Serotonin#The 5-HT system|5-HT_2A receptor]]. Entactogenic and stimulant effects are due to their action as [[Releasing Agent|releasing agents]] of [[serotonin]], [[adrenaline]] and [[noradrenaline]] or as [[Agonist#Agonists|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 [[Thought acceleration|cognitive]] and [[Stimulation|physical stimulation]] within the user.

== List of substituted amphetamines ==

''Note: This list does not include [[Substituted Phenethylamine|phenethylamines]], [[Substituted phenidate|phenidates]], [[substituted cathinone|cathinones]], [[substituted MDxx|MDxxs]], [[DOx|DOxs]], [[Benzofuran|Benzofurans]] or [[substituted aminoindane|aminoindanes]].''

{| class="wikitable"

! scope="col" | '''Compound'''

! scope="col" style="width: 50px;" | '''R₂'''

! scope="col" style="width: 50px;" | '''R₃'''

! scope="col" style="width: 50px;" | '''R₄'''

! scope="col" style="width: 50px;" | '''R₅'''

! scope="col" style="width: 50px;" | '''R₆'''

! scope="col" style="width: 50px;" | '''R_α'''

! scope="col" style="width: 50px;" | '''R_β'''

! scope="col" style="width: 200px;" | '''R_N1'''

! scope="col" style="width: 200px;" | '''R_N2'''

! scope="col" | '''Structure'''

| [[Amphetamine]] || H || H || H || H || H || H || H || H || H || [[File:Amphetamine2.png|170px]]

| [[Methamphetamine]] || H || H || H || H || H || H || H || H || CH₃ || [[File:Meth.png|170px]]

| Ethylamphetamine (''Etilamfetamine'') || H || H || H || H || H || H || H || H || CH₃ || [[File:Ethylamphetamine.png|170px]]

| Propylamphetamine || H || H || H || H || H || H || H || H || CH₂CH₂CH₃ || [[File:Propylamphetamine.png|170px]]

| Isopropylamphetamine || H || H || H || H || H || H || H || H || CH(CH₃)₂ || [[File:Isopropylamphetamine.png|170px]]

| [[Bromo-DragonFLY]] || OCH=CH- || - || Br || OCH=CH- || - || H || H || H || H || [[File:Bromo-DragonFLY.png|170px]]

| [[Lisdexamfetamine]] || H || H || H || H || H || H || H || H || COCH(NH₂)(CH₂)₄NH₂ || [[File:Lisdexamphetamine.png|170px]]

| Clobenzorex || H || H || H || H || H || H || H || H || CH₂C₆H₄Cl || [[File:Clobenzorex.png|170px]]

| Dimethylamphetamine || H || H || H || H || H || H || H || CH₃ || CH₃ || [[File:Dimethylamphetamine.png|170px]]

| Selegiline || H || H || H || H || H || H || H || CH₃ || CH₂CCH || [[File:Selegiline.png|170px]]

| Benzphetamine || H || H || H || H || H || H || H || CH₃ || CH₂C₆H₅ || [[File:Benzphetamine.svg|170px]]

| Ortetamine || CH₃ || H || H || H || H || H || H || H || H || [[File:Ortetamine.png|170px]]

| 3-Methylamphetamine || H || CH₃ || H || H || H || H || H || H || H || [[File:3-Methylamphetamine.png|170px]]

| 4-Methylamphetamine || H || H || CH₃ || H || H || H || H || H || H || [[File:4-Methylamphetamine.png|170px]]

| 4-MMA || H || H || CH₃ || H || H || H || H || H || CH₃ || [[File:4-MMA.png|170px]]

| Xylopropamine || H || CH₃ || CH₃ || H || H || H || H || H || H || [[File:Xylopropamine.png|170px]]

| β-methylamphetamine || H || H || H || H || H || H || CH₃ || H || H || [[File:Beta-methylamphetamine.png|170px]]

| [[2-FA]] || F || H || H || H || H || H || H || H || H || [[File:2-FA.png|170px]]

| [[2-FMA]] || F || H || H || H || H || H || H || H || CH₃ || [[File:2fluoromethamphetamine.png|170px]]

| 3-FA || H || F || H || H || H || H || H || H || H || [[File:3-FA.png|170px]]

| 3-FMA || H || F || H || H || H || H || H || H || CH₃ || [[File:3-FMA.png|170px]]

| 3-FEA || H || F || H || H || H || H || H || H || CH₂CH₃ || [[File:3-FEA.png|170px]]

| [[4-FA]] || H || H || F || H || H || H || H || H || H || [[File:4fa.png|170px]]

| 4-FMA || H || H || F || H || H || H || H || H || CH₃ || [[File:4-FMA.png|170px]]

| 4-CA || H || H || Cl || H || H || H || H || H || H || [[File:4-CA.png|170px]]

| 4-BA || H || H || Br || H || H || H || H || H || H || [[File:4-BA.png|170px]]

| 4-IA || H || H || I || H || H || H || H || H || H || [[File:4-IA.png|170px]]

| DCA || H || Cl || Cl || H || H || H || H || H || H || [[File:DCA.png|170px]]

| 4-HA || H || H || OH || H || H || H || H || H || H || [[File:4-HA.png|170px]]

| 4-HMA || H || H || OH || H || H || H || H || H || CH₃ || [[File:4-HMA.png|170px]]

| 3,4-DHA || H || OH || OH || H || H || H || H || H || H || [[File:3,4-DHA.png|170px]]

| OMA || OCH₃ || H || H || H || H || H || H || H || H || [[File:OMA.png|170px]]

| 3-MA || H || OCH₃ || H || H || H || H || H || H || H || [[File:3-MA.png|170px]]

| MMMA || H || OCH₃ || H || H || H || H || H || H || CH₃ || [[File:MMMA.png|170px]]

| MMA || H || OCH₃ || CH₃ || H || H || H || H || H || H || [[File:MMA.png|170px]]

| [[PMA]] || H || H || OCH₃ || H || H || H || H || H || H || [[File:PMA.png|171px]]

| [[PMMA]] || H || H || OCH₃ || H || H || H || H || H || CH₃ || [[File:PMMA.png|171px]]

| PMEA || H || H || OCH₃ || H || H || H || H || H || CH₂CH₃ || [[File:PMEA.png|170px]]

| 4-ETA || H || H || OCH₂CH₃ || H || H || H || H || H || H || [[File:4-ETA.png|170px]]

| 4-MTA || H || H || SCH₃ || H || H || H || H || H || H || [[File:4-MTA.png|170px]]

| Cathine || H || H || H || H || H || H || OH || H || H || [[File:Cathine.png|170px]]

*[[Psychedelics]]

*[[Entactogens]]