Substituted phenethylamine
Substituted phenethylamines (or simply phenethylamines) are a chemical class 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.
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.
Many substituted phenethylamines are psychoactive drugs which belong to a variety of different drug classes, including central nervous system stimulants (e.g., amphetamine), hallucinogens (e.g., dl-2,5-dimethoxy-4-methylamphetamine DOM), entactogens (e.g., 3,4-methylenedioxyamphetamine MDA), appetite suppressants (e.g. phentermine), nasal decongestants and bronchodilators (e.g., levomethamphetamine and pseudoephedrine), antidepressants (e.g. bupropion and phenelzine), antiparkinson agents (e.g., selegiline), and vasopressors (e.g., ephedrine), 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, adrenaline, phenethylamine itself, tyramine, thyronamine, and iodothyronamine) – are substituted phenethylamines. Several notable recreational drugs, such as MDMA (ecstasy), methamphetamine, and cathinone, are also members of the class. All of the substituted amphetamines and substituted methylenedioxyphenethylamines are substituted phenethylamines as well.
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chemical class
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organic compound
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phenethylamine
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derivative
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substituting
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hydrogen atom
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substituent
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structural formula
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phenyl ring
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amino (NH) group
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sidechain
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hydrogen (H) atom
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specific group of atoms
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psychoactive drug
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drug class
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central nervous system
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stimulant
Concept
Q179452
amphetamine
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hallucinogen
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2,5-dimethoxy-4-methylamphetamine
UNK
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entactogen
Concept
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3,4-methylenedioxyamphetamine
Concept
Q567709
appetite suppressant
Concept
Q418157
phentermine
Concept
Q430719
nasal decongestant
Concept
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bronchodilator
Concept
Q402846
levomethamphetamine
Concept
Q263958
pseudoephedrine
Concept
Q76560
antidepressant
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Q834280
bupropion
Concept
Q1747559
phenelzine
Concept
None
antiparkinson agent
UNK
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selegiline
Concept
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vasopressor
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Q219626
ephedrine
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monoamine neurotransmitter
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mechanism of action
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biological target
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endogenous
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hormone
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monoamine neurotransmitter
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trace amine
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dopamine
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norepinephrine
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adrenaline
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phenethylamine
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tyramine
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thyronamine
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iodothyronamine
UNK
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recreational drug
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MDMA
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methamphetamine
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cathinone
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substituted amphetamine
Concept
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substituted methylenedioxyphenethylamine
Concept
Q422693
Substituted phenethylamine
Concept
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subclass of
subclass of
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subclass of
subclass of
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