Substituted phenethylamine

Substituted phenethylamine
Drug class

Phenethylamine structure diagram

The structural formula of phenethylamine with marked substitution points. Phenethylamine is obtained when
R2=R3=R4=R5=R6=RN=Rα=Rβ=H.
Class identifiers
Chemical class Substituted derivatives of phenethylamine
The structural formula of phenethylamine

Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure;[note 1] 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 (NH2) group via an ethyl (−CH2–CH2−) 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 aka DOM), entactogens (e.g., 3,4-methylenedioxyamphetamine aka 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.

List of substituted phenethylamines

Selected Phenethylamines
Short Name RN Rα Rβ R2 R3 R4 R5 Full Name Biologic activity
meta-Tyramine OH 3-hydroxyphenethylamine Trace amine
para-Tyramine OH 4-hydroxyphenethylamine Trace amine
Dopamine OH OH 3,4-dihydroxyphenethylamine Catecholamine neurotransmitter
Epinephrine (Adrenaline) CH3 OH OH OH β,3,4-trihydroxy-N-methylphenethylamine Catecholamine neurotransmitter/Fight or Flight hormone
Norepinephrine (Noradrenaline) OH OH OH β,3,4-trihydroxyphenethylamine Catecholamine neurotransmitter/Fight or Flight hormone
meta-Octopamine OH OH β,3-dihydroxyphenethylamine Trace amine
para-Octopamine OH OH β,4-dihydroxyphenethylamine Trace aminergic α-adrenoceptor agonist
Phenylephrine CH3 OH OH β,3-dihydroxy-N-methylphenethylamine α-adrenergic agonist; decongestant
6-Hydroxydopamine OH OH OH 2,4,5-trihydroxyphenethylamine neurotoxic agent for the dopamine and norepinephrine receptors
Salbutamol C(CH3)3 OH OH CH2OH β,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamine Short-action β2-adrenergic agonist
β-Methylphenethylamine CH3 β-methylphenethylamine Stimulant
Amphetamine CH3 α-methylphenethylamine Monoamine releasing agent; Stimulant
N-Methylphenethylamine CH3 N-methylphenethylamine Trace amine; Endogenous amphetamine isomer
Methamphetamine CH3 CH3 N-methylamphetamine; N,α-dimethylphenethylamine Monoamine releasing agent; Stimulant; dopaminergic neurotoxin
Phentermine 2CH3 α-methylamphetamine; α,α-dimethylphenethylamine Stimulant, anorectic
Ortetamine CH3 CH3 2-methylamphetamine; 2,α-dimethylphenethylamine Stimulant, anorectic
Methylphenidate -CH2-CH2-CH2-CH2- C(OCH3)=O N,α-butylene-β-methoxycarbonylphenethylamine NDRI; Stimulant
Ephedrine / Pseudoephedrine CH3 CH3 OH N-methyl-β-hydroxyamphetamine Releasing agent; stimulant; decongestant
Cathine CH3 OH d-β-hydroxyamphetamine Somewhat selective norepinephrine releasing agent
Cathinone CH3 =O β-ketoamphetamine Selective norepinephrine and dopamine releasing agent
Methcathinone CH3 CH3 =O N-methylcathinone Selective norepinephrine and dopamine releasing agent
Mephedrone CH3 CH3 =O CH3 4-methylmethcathinone Stimulant, unknown pharmacodynamics actions
Ethcathinone CH2CH3 CH3 =O N-ethylcathinone Stimulant and Norepinephrine releasing agent
Bupropion C(CH3)3 CH3 =O Cl 3-chloro-N-tert-butyl-β-ketoamphetamine NDRI
Selegiline CH2)CHCH []
Norfenfluramine CH3 CF3 3-trifluoromethyl-amphetamine SSRA
Fenfluramine CH2CH3 CH3 CF3 3-trifluoromethyl-N-ethylamphetamine SSRA
5-APB CH3 -CH=CH-O- 5-(2-aminopropyl)benzofuran stimulant, entactogen
6-APB CH3 -O-CH=CH- 6-(2-aminopropyl)benzofuran stimulant, entactogen
MDA CH3 -O-CH2-O- 3,4-methylenedioxy-amphetamine Stimulant, psychedelic, entactogen
MDEA CH2CH3 CH3 -O-CH2-O- 3,4-methylenedioxy-N-ethylamphetamine psychedelic, entactogen and releasing agent
MDMA CH3 CH3 -O-CH2-O- 3,4-methylenedioxy-N-methylamphetamine psychedelic, entactogen and releasing agent
MDMC CH3 CH3 =O -O-CH2-O- 3,4-methylenedioxymethcathinone psychedelic, entactogen and releasing agent
Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxyphenethylamine Serotonergic Psychedelic
Proscaline OCH3OCH2CH2CH3 OCH3 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine Stimulant, entactogen and euphoriant
Metaescaline OCH2CH3 OCH3 OCH3 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine Serotonergic Psychedelic, stimulant, entactogen and euphoriant
Allylescaline OCH3OCH2CH1CH2 OCH3 4-Allyloxy-3,5-dimethyloxyphenylethylamine Stimulant, entactogen and euphoriant
Asymbescaline OCH2CH3OCH2CH3 OCH3 3,4-Diethoxy-5-methoxyphenethylamine Psychedelic and euphoriant
DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methylamphetamine psychedelic
DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromoamphetamine Psychedelic
DOI CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodoamphetamine Psychedelic
DON CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitroamphetamine Stimulant
DOC CH3 OCH3 Cl OCH3 2,5-dimethoxy-4-chloroamphetamine Psychedelic
2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromophenethylamine Psychedelic, stimulant, entactogen and euphoriant
βk-2C-B =O OCH3 Br OCH3 2,5-dimethoxy-4-bromo-β-ketophenethylamine Psychedelic, stimulant, entactogen and euphoriant
2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chlorophenethylamine Psychedelic
2C-I OCH3 I OCH3 2,5-dimethoxy-4-iodophenethylamine Psychedelic, stimulant
2C-D OCH3 CH3 OCH3 2,5-dimethoxy-4-methylphenethylamine Psychedelic, stimulant
2C-E OCH3 CH2-CH3 OCH3 2,5-dimethoxy-4-ethylphenethylamine Psychedelic
2C-P OCH3 CH2-CH3-CH3 OCH3 2,5-dimethoxy-4-propylphenethylamine Entactogen, euphoriant and Psychedelic
2C-F OCH3 F OCH3 2,5-dimethoxy-4-fluorophenethylamine None
2C-N OCH3 NO2 OCH3 2,5-dimethoxy-4-nitrophenethylamine euphoriant
2C-T-2 OCH3 S-CH2CH3 OCH3 2,5-dimethoxy-4-ethylthio-phenethylamine Psychedelic
2C-T-4 OCH3 S-CH(CH3)2 OCH3 2,5-dimethoxy-4-isopropylthio-phenethylamine Psychedelic
2C-T-7 OCH3 S-CH2CH2CH3 OCH3 2,5-dimethoxy-4-propylthio-phenethylamine Psychedelic
2C-T-8 OCH3 S-CH2-C3H5 OCH3 2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine Psychedelic
2C-T-19 OCH3 S-C(CH3)3 OCH3 2,5-dimethoxy-4-tert-butylthio-phenethylamine Psychedelic
2C-T-21 OCH3 S-CH2-CH2-F OCH3 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine Psychedelic and euphoriant
25B-NBOMe CH2-C6H4-OCH3 OCH3 Br OCH3 2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25C-NBOMe CH2-C6H4-OCH3 OCH3 Cl OCH3 2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25I-NBOMe CH2-C6H4-OCH3 OCH3 I OCH3 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25D-NBOMe CH2-C6H4-OCH3 OCH3 CH2 OCH3 2-(4-methyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25E-NBOMe CH2-C6H4-OCH3 OCH3 CH2-CH3 OCH3 2-(4-ethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25P-NBOMe CH2-C6H4-OCH3 OCH3 CH2-CH3-CH3 OCH3 2-(4-propyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25F-NBOMe CH2-C6H4-OCH3 OCH3 F OCH3 2-(4-fluoro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
Mescaline-NBOMe CH2-C6H4-OCH3 OCH3 OCH3 OCH3 N-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanamine Psychedelic
25I-NBOH CH2–C6H4–OH OCH3 I OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine Psychedelic
25C-NBOH CH2–C6H4–OH OCH3 Cl OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine Psychedelic
25B-NBOH CH2–C6H4–OH OCH3 Br OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine Psychedelic
25I-NBF CH2–C6H4–F OCH3 I OCH3 N-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine Psychedelic
Amfepramone (diethylpropion) C2H5, C2H5[note 2] CH3 =O N-diethyl-β-ketoamphetamine Anorectic.
Short Name RN Rα Rβ R2 R3 R4 R5 Full Name Biologic activity

Detection

method Requirement
UV spectrometry Reagent needed

See also

Notes

  1. ↑ In other words, all of the compounds that belong to this class are structural analogs of phenethylamine.
  2. ↑ Two ethyl groups attached to the amine group

References

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