Substituted phenethylamines include a wide variety of drug classes. This includes but is not limited to psychotropic drugs (including hallucinogens such as dl-2,5-dimethoxy-4-methylamphetamine a.k.a. DOM), central nervous system stimulants (e.g. amphetamine), appetite depressants (e.g. phentermine), antilipemic agents, vasoconstrictors (including nasal decongestants such as levomethamphetamine and pseudoephedrine), bronchodilators, cardiotonic agents, vasodilators, calcium channel regulators and blockers (these properties may be concentration dependent), antidepressants (e.g. bupropion, phenelzine, and tranylcypromine), neuroprotective agents and Antiparkinson agents.
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 |
|
|
|
|
OCH3 |
OCH2CH2CH3 |
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 |
|
|
|
|
OCH3 |
OCH2CH1CH2 |
OCH3 |
4-Allyloxy-3,5-dimethyloxyphenylethylamine |
Stimulant, entactogen and euphoriant |
Asymbescaline |
|
|
|
|
OCH2CH3 |
OCH2CH3 |
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-9 |
|
|
|
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 1] |
CH3 |
=O |
|
|
|
|
N-diethyl-β-ketoamphetamine |
Anorectic. |
Short Name |
RN |
Rα |
Rβ |
R2 |
R3 |
R4 |
R5 |
Full Name |
Biologic activity |