Substituted phenethylamines

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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]


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 Phenethylamine.svg
Dopamine H OH OH H H H Dopamine.svg
Norepinephrine H OH OH H H OH Norepinephrine.svg
Epinephrine H OH OH H CH3 OH Epinephrine.svg
Salbutamol H CH2OH OH H CCH3CH3CH3 OH Salbutamol.svg
Mescaline H OCH3 OCH3 OCH3 H H Mescaline.svg
Escaline H OCH3 OCH2CH3 OCH3 H H Escaline.svg
Proscaline H OCH3 OCH2CH2CH3 OCH3 H H Proscaline.svg
Allylescaline H OCH3 OCH2CH=CH2 OCH3 H H Allylescaline.svg
Methallylescaline H OCH3 OCH2C=CH2CH3 OCH3 H H Methallylescaline.svg

See also

External links


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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.