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Substituted amphetamines: Difference between revisions

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[[File:samphetamine.png|thumb|right|301px||Generic structure of an amphetamine molecule]]
[[File:samphetamine.png|thumb|right|301px||Substitutive 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''' (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 substance index|psychoactive substances]], which typically produce [[stimulant]] effects, [[entactogen|entactogenic]] effects, and/or [[psychedelic]] effects.


==Chemistry==
==Chemistry==
[[File:Phenethylamine.png|thumb|right|245px|Generic structure of a ''phenethylamine'' molecule]]
[[File:Phenethylamine.png|thumb|right|245px|Substitutive structure of a ''phenethylamine'' molecule.]]


Substituted amphetamines are a class of chemicals that have structures based on that of [[amphetamine]] with different substitutions at varying 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 only unsubstituted member of the substituted amphetamine class, amphetamine is also considered a [[Substituted Phenethylamines|substituted phenethylamine]].
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 [[Phenethylamine|substituted phenethylamine]].


==Pharmacology==
==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 [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> 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.
Psychoactive substances of the substituted amphetamine class typically produce effects through [[dopamine|dopaminergic]], [[serotonin|serotonergic]], and [[norepinephrine|adrenergic]] pathways. Psychedelic effects can be attributed to action on the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]].{{citation needed}} Stimulant and entactogenic effects are due to their action as [[Releasing Agent|releasing agents]] of [[dopamine]], [[serotonin]], [[epinephrine]] and [[norepinephrine]] or as [[Agonist#Agonists|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 [[Thought acceleration|cognitive]] and [[Stimulation|physical stimulation]] within the user.{{citation needed}}


== List of substituted amphetamines ==
== 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]].''
''Note: This list does not include [[Phenidate|phenidates]], [[Substituted cathinone|cathinones]], [[Substituted MDxx|MDxxs]], [[DOx|DOxs]], [[Benzofuran|Benzofurans]], or [[Substituted aminoindane|aminoindanes]].''
{| class="wikitable"
{| class="wikitable"
|-
|-
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| [[3-FEA]] || H || F || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:3-FEA.png|170px]]
| [[3-FEA]] || H || F || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:3-FEA.png|170px]]
|-
|-
| [[Fenfluramine]] || H || CF<sub>3</sub> || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:Fenfluramine.png|170px]]
| Fenfluramine || H || CF<sub>3</sub> || H || H || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:Fenfluramine.png|170px]]
|-
|-
| [[Norfenfluramine]] || H || CF<sub>3</sub> || H || H || H || H || H || H || H || [[File:Norfenfluramine.png|170px]]
| Norfenfluramine || H || CF<sub>3</sub> || H || H || H || H || H || H || H || [[File:Norfenfluramine.png|170px]]
|-
|-
| [[4-FA]] || H || H || F || H || H || H || H || H || H || [[File:4fa.png|170px]]
| [[4-FA]] || H || H || F || H || H || H || H || H || H || [[File:4fa.png|170px]]
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|-
|-
| 4-CA || H || H || Cl || H || H || H || H || H || H || [[File:4-CA.png|170px]]
| 4-CA || H || H || Cl || H || H || H || H || H || H || [[File:4-CA.png|170px]]
|-
| 4-CMA || H || H || Cl || H || H || H || H || H || CH<sub>3</sub> || [[4-CMA_structure.png|170px]]
|-
|-
| 4-BA || H || H || Br || H || H || H || H || H || H || [[File:4-BA.png|170px]]
| 4-BA || H || H || Br || H || H || H || H || H || H || [[File:4-BA.png|170px]]
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==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Psychedelics]]
*[[Phenethylamine]]
*[[Phenethylamines]]
*[[Entactogens]]
*[[Stimulants]]
*[[Stimulants]]
*[[Entactogen]]
*[[Psychedelic]]


==References==
==References==
{{references}}
{{references}}

Revision as of 23:55, 12 April 2017

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
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
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
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
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

References

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