Substituted phenethylamine

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The structure of substituted phenethylamines. Phenethylamine itself is obtained when R2=R3=R4=R5=RN=Rα=Rβ = H.

Substituted phenethylamines (or simply phenethylamines) are organic compounds which may be thought of as being derived from phenethylamine itself. The molecular structures of all phenethylamines contain a phenyl ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted phenethylamines, the phenyl ring, sidechain and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

Some are psychoactive drugs, including stimulants, psychedelics, and entactogens, which exert their effects primarily through modulation of the monoamine neurotransmitter systems. Others, such as dopamine and epinephrine are neurotransmitters. The substituted phenethylamines include the substituted amphetamines, the substituted methylenedioxyphenethylamines and a large group of alkaloids derived from phenethylamines. This includes tetrahydroisoquinolines, benzylisoquinolines, protoberberines, aporphines, morphinans, protopines and narcotine.[1]p. 74

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 blockers, antidepressants (e.g. bupropion, phenelzine, and tranylcypromine), neuroprotective agents and Antiparkinson agents.

Substituted phenethylamines are known to act as adrenergic agents (including adrenergic uptake inhibitors such as methamphetamine, adrenergic beta-agonists like methoxyphenamine and the adrenergic alpha-agonist mephentermine), antilipemic agents (e.g. benfluorex), dopamine agents (including dopamine uptake inhibitors such as bupropion), serotonin agents (including serotonin agonists such as 2,5-dimethoxy-4-bromoamphetamine and the serotonin uptake inhibitor fenfluramine), calcium channel blockers (e.g. prenylamine and verapamil) and monoamine oxidase inhibitors (e.g. selegiline).

List of substituted phenethylamines[edit]

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 Endogenous amphetamine isomer; Trace amine
Methamphetamine CH3 CH3 N-methylamphetamine Monoamine releasing agent; Stimulant; dopaminergic neurotoxin
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
Norfenfluramine CH3 CF3 3-trifluoromethyl-amphetamine SSRA
Fenfluramine CH2CH3 CH3 CF3 3-trifluoromethyl-N-ethyl-amphetamine SSRA
Phentermine 2CH3 α,α-dimethylphenethylamine Stimulant, anorectic
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-methylenedioxyamphetamine 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

See also[edit]

Notes[edit]

  1. ^ Two ethyl groups attached to the amine group

References[edit]

  1. ^ Hoffer A. The Hallucinogens. New York: Academic Press, 1967.