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{{Information/Substituted phenethylamines}}
 
{{For|the eponymous compound|Phenethylamine (compound)}}  
[[File:Substituted_phenethylamine.svg|thumb|right|299px||Substitutive structure of a ''phenethylamine'' molecule.]]
'''Substituted phenethylamines''' (also referred to as '''phenethylamines''') are a group of organic compounds that are based upon the [[phenethylamine]] structure. The class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.
'''Substituted phenethylamines''' (also referred to as '''phenethylamines''') are a group of organic compounds that are based upon the [[phenethylamine]] structure. The class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.


Many substituted phenethylamines are psychoactive substances which belong to a variety of different classes, including central nervous system stimulants (e.g., amphetamine), [[hallucinogens]] (e.g. [[DOM]]), [[entactogens]] (e.g. [[MDMA]]), appetite suppressants (e.g. phentermine), antidepressants (e.g. [[bupropion]] and phenelzine), among others. Many of these psychoactive compounds exert their pharmacological effects primarily by modulating monoamine neurotransmitter systems; however, there is no mechanism of action or biological target that is common to all members of this subclass.
Many substituted phenethylamines are psychoactive substances which belong to a variety of different classes, including central nervous system stimulants (e.g., amphetamine), [[hallucinogens]] (e.g. compounds listed in [[PiHKAL]]), [[entactogens]] (e.g. [[MDMA]]), appetite suppressants (e.g. phentermine), antidepressants (e.g. [[bupropion]] and phenelzine), among others.  
 
Many of these psychoactive compounds exert their pharmacological effects primarily by modulating monoamine neurotransmitter systems; however, there is no mechanism of action or biological target that is common to all members of this subclass.


Numerous endogenous compounds – including hormones, monoamine neurotransmitters, and many trace amines (e.g. [[dopamine]], [[norepinephrine]], tyramine) – are substituted phenethylamines. Several notable recreational drugs, such as [[MDMA]], [[methamphetamine]], and [[cathinone]], are also members of the class. All of the substituted amphetamines and substituted methylenedioxyphenethylamines are substituted phenethylamines as well.
Numerous endogenous compounds – including hormones, monoamine neurotransmitters, and many trace amines (e.g. [[dopamine]], [[norepinephrine]], tyramine) – are substituted phenethylamines. Several notable recreational drugs, such as [[MDMA]], [[methamphetamine]], and [[cathinone]], are also members of the class. All of the substituted amphetamines and substituted methylenedioxyphenethylamines are substituted phenethylamines as well.
Phenethylamines have been identified as the fourth largest category of substances with a total of 102, falling behind [[Cathinone|cathinones]] with 156 substances and [[Cannabinoid|cannabinoids]] with 209 substances, according to a report by the EU Early Warning System.<ref>{{cite book | vauthors=((European Monitoring Centre for Drugs and Drug Addiction)) | date= 2021 | title=European drug report 2021 :trends and developments. | publisher=Publications Office | url=https://data.europa.eu/doi/10.2810/725386}}</ref>


==Chemistry==
==Chemistry==
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==List of substituted phenethylamines==
==List of substituted phenethylamines==
''Note: This list does not include [[Substituted amphetamine|amphetamines]], [[Substituted phenidate|phenidates]], [[substituted cathinone|cathinones]], [[substituted MDxx|MDxx]], [[2C-x]], [[DOx]], [[25x-NBOMe]], [[25x-NBOH]], [[Benzofuran|Benzofurans]], or [[substituted aminoindane|aminoindanes]]''
''This table does not include the following groups of substituted phenethylamines:''
{{columns-list|colwidth=10em|
* [[2C-x]]
* [[25x-NBOH]]  
* [[25x-NBOMe]]
* [[Aminoindanes]]
* [[Amphetamines]]
* ↳''[[DOx]]''
* ↳''[[MDxx]]''
* [[benzofuran|Benzofurans]]
* [[Cathinones]]
* [[Substituted phenidate|Phenidates]]
}}
{| class="wikitable"
{| class="wikitable"
|-
|-
! scope="col" | '''Compound'''
! scope="col" |'''Compound'''
! scope="col" style="width: 50px;" | '''R<sub>2</sub>'''
! scope="col" style="width: 50px;" |'''R<sub>2</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>3</sub>'''
! scope="col" style="width: 50px;" |'''R<sub>3</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>4</sub>'''
! scope="col" style="width: 50px;" |'''R<sub>4</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>5</sub>'''
! scope="col" style="width: 50px;" |'''R<sub>5</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>N</sub>'''
! scope="col" style="width: 50px;" |'''R<sub>N</sub>'''
! scope="col" | '''Structure'''
! scope="col" style="width: 50px;" |'''R<sub>β</sub>'''
! scope="col" |'''Structure'''
|-
|-
| [[Phenethylamine]] || H || H || H || H || H || [[File:phenethylamine.svg|200px]]
|[[Phenethylamine]]||H||H||H||H||H||H||[[File:phenethylamine.svg|200px]]
|-
|-
| [[2C-B-FLY]] || OCH<sub>2</sub>CH<sub>2</sub>- || - || Br || OCH<sub>2</sub>CH<sub>2</sub>- || H || [[File:2C-B-FLY.svg|200px]]
|[[Dopamine]]||H||OH||OH||H||H||H||[[File:Dopamine.svg|200px]]
|-
|-
| [[Mescaline]] || H || OCH<sub>3</sub> || OCH<sub>3</sub> || OCH<sub>3</sub> || H || [[File:Mescaline.svg|200px]]
|[[Norepinephrine]]||H||OH||OH||H||H||OH||[[File:Norepinephrine.svg|200px]]
|-
|-
| [[Escaline]] || H || OCH<sub>3</sub> || OCH<sub>2</sub>CH<sub>3</sub> || OCH<sub>3</sub> || H || [[File:Escaline.svg|200px]]
|[[Epinephrine]]||H||OH||OH||H||CH<sub>3</sub>||OH||[[File:Epinephrine.svg|200px]]
|-
|-
| [[Allylescaline]] || H || OCH<sub>3</sub> || OCH<sub>3</sub> || OCH<sub>3</sub> || H || [[File:Allylescaline.svg|201px]]
|[[Salbutamol]]||H||CH<sub>2</sub>OH||OH||H||CCH<sub>3</sub>CH<sub>3</sub>CH<sub>3</sub>||OH||[[File:Salbutamol.svg|200px]]
|-
|-
| [[Methallylescaline]] || H || OCH<sub>3</sub> || OCH<sub>3</sub> || OCH<sub>3</sub> || H || [[File:Methallylescaline.svg|200px]]
|[[Mescaline]]||H||OCH<sub>3</sub>||OCH<sub>3</sub>||OCH<sub>3</sub>||H||H||[[File:Mescaline.svg|200px]]
|-
|-
| [[Proscaline]] || H || OCH<sub>3</sub> || OCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || OCH<sub>3</sub> || H || [[File:Proscaline.svg|200px]]
|[[Escaline]]||H||OCH<sub>3</sub>||OCH<sub>2</sub>CH<sub>3</sub>||OCH<sub>3</sub>||H||H||[[File:Escaline.svg|200px]]
|-
|[[Proscaline]]||H||OCH<sub>3</sub>||OCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||OCH<sub>3</sub>||H||H||[[File:Proscaline.svg|200px]]
|-
|[[Allylescaline]]||H||OCH<sub>3</sub>||OCH<sub>2</sub>CH=CH<sub>2</sub>||OCH<sub>3</sub>||H||H||[[File:Allylescaline.svg|201px]]
|-
|[[Methallylescaline]]||H||OCH<sub>3</sub>||OCH<sub>2</sub>C=CH<sub>2</sub>CH<sub>3</sub>||OCH<sub>3</sub>||H||H||[[File:Methallylescaline.svg|200px]]
|-
|-
|}
|}


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Lysergamide]]
*[[Lysergamide]]
*[[Tryptamine]]
*[[Tryptamine]]
*[[Psychedelics]]
*[[Psychedelics]]
*[[PiHKAL]]


==External links==
==External links==
*[[wikipedia:Substituted phenethylamine|Substituted phenethylamine(Wikipedia)]]
 
*[[wikipedia:Substituted phenethylamine|Substituted phenethylamine (Wikipedia)]]
*[https://en.wikipedia.org/wiki/List_of_naturally_occurring_phenethylamines List of naturally occurring phenethylamines (Wikipedia)]
*[https://en.wikipedia.org/wiki/List_of_naturally_occurring_phenethylamines List of naturally occurring phenethylamines (Wikipedia)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=142 Phenethylamine (PiHKAL / Isomer Design)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=142 Phenethylamine (PiHKAL / Isomer Design)]
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{{references}}
{{references}}
<references />
<references />
[[Category:Chemical class]]
[[Category:Phenethylamine|*]]
{{#set:Featured=true}}

Latest revision as of 23:05, 21 April 2024

Notes about routes of administration: There's not a single trip report in PiHKAL in which the subject is smoking or vaporizing the phenethylamine compound. However, 25I-NBOMe (a substituted phenethylamine not listed in the book, albeit very toxic) has been smoked.[1]
For the eponymous compound, see Phenethylamine (compound).
Substitutive structure of a phenethylamine molecule.

Substituted phenethylamines (also referred to as phenethylamines) are a group of organic compounds that are based upon the phenethylamine structure. The class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.

Many substituted phenethylamines are psychoactive substances which belong to a variety of different classes, including central nervous system stimulants (e.g., amphetamine), hallucinogens (e.g. compounds listed in PiHKAL), entactogens (e.g. MDMA), appetite suppressants (e.g. phentermine), antidepressants (e.g. bupropion and phenelzine), among others.

Many of these psychoactive compounds exert their pharmacological effects primarily by modulating monoamine neurotransmitter systems; however, there is no mechanism of action or biological target that is common to all members of this subclass.

Numerous endogenous compounds – including hormones, monoamine neurotransmitters, and many trace amines (e.g. dopamine, norepinephrine, tyramine) – are substituted phenethylamines. Several notable recreational drugs, such as MDMA, methamphetamine, and cathinone, are also members of the class. All of the substituted amphetamines and substituted methylenedioxyphenethylamines are substituted phenethylamines as well.

Phenethylamines have been identified as the fourth largest category of substances with a total of 102, falling behind cathinones with 156 substances and cannabinoids with 209 substances, according to a report by the EU Early Warning System.[2]

Chemistry

The structural formula of any substituted phenethylamine contains a phenyl ring that is joined to an amino (NH) group via a two-carbon sidechain. Hence, any substituted phenethylamine can be classified according to the substitution of hydrogen (H) atoms on phenethylamine's phenyl ring, sidechain, or amino group with a specific group of atoms.

List of substituted phenethylamines

This table does not include the following groups of substituted phenethylamines:

Compound R2 R3 R4 R5 RN Rβ Structure
Phenethylamine H H H H H H
Dopamine H OH OH H H H
Norepinephrine H OH OH H H OH
Epinephrine H OH OH H CH3 OH
Salbutamol H CH2OH OH H CCH3CH3CH3 OH
Mescaline H OCH3 OCH3 OCH3 H H
Escaline H OCH3 OCH2CH3 OCH3 H H
Proscaline H OCH3 OCH2CH2CH3 OCH3 H H
Allylescaline H OCH3 OCH2CH=CH2 OCH3 H H
Methallylescaline H OCH3 OCH2C=CH2CH3 OCH3 H H

See also

References

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  1. ↑ "2C-I-NBOMe (25I) Effects". Erowid. 
  2. ↑ European Monitoring Centre for Drugs and Drug Addiction (2021). European drug report 2021 :trends and developments. Publications Office. 


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