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File:Phenethylamine rests.svg

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

Selected Phenethylamines
Short Name RN Rα Rβ R2 R3 R4 R5 Full Name Biologic activity
meta-Tyramine OH 3-hydroxyphenethylamine ?
para-Tyramine OH 4-hydroxyphenethylamine Peripheral catecholamine releasing agent
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 ?
para-Octopamine OH OH β,4-dihydroxyphenethylamine α-adrenergic sympathomimetic
Phenylephrine CH3 OH OH β,3-dihydroxy-N-methylphenethylamin 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; stimulant
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
Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxyphenethylamine Serotonergic Psychedelic
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
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
DON CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitroamphetamine
DOC CH3 OCH3 Cl OCH3 2,5-dimethoxy-4-chloroamphetamine
2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromophenethylamine
2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chlorophenethylamine
2C-I OCH3 I OCH3 2,5-dimethoxy-4-iodophenethylamine
2C-D OCH3 CH3 OCH3 2,5-dimethoxy-4-methylphenethylamine
2C-E OCH3 CH2-CH3 OCH3 2,5-dimethoxy-4-ethylphenethylamine
2C-P OCH3 CH2-CH3-CH3 OCH3 2,5-dimethoxy-4-propylphenethylamine
2C-F OCH3 F OCH3 2,5-dimethoxy-4-fluorophenethylamine
2C-N OCH3 NO2 OCH3 2,5-dimethoxy-4-nitrophenethylamine
2C-T-2 OCH3 S-CH2CH3 OCH3 2,5-dimethoxy-4-ethylthio-phenethylamine
2C-T-4 OCH3 S-CH(CH3)2 OCH3 2,5-dimethoxy-4-isopropylthio-phenethylamine
2C-T-7 OCH3 S-CH2CH2CH3 OCH3 2,5-dimethoxy-4-propylthio-phenethylamine
2C-T-8 OCH3 S-CH2-C3H5 OCH3 2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine
2C-T-9 OCH3 S-C(CH3)3 OCH3 2,5-dimethoxy-4-tert-butylthio-phenethylamine
2C-T-21 OCH3 S-CH2-CH2-F OCH3 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine
25I-NBOMe CH2-C6H4-OCH3 OCH3 I OCH3 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
25C-NBOMe CH2-C6H4-OCH3 OCH3 Cl OCH3 2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
25B-NBOMe CH2-C6H4-OCH3 OCH3 Br OCH3 2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
5-APB CH3 -CH=CH-O- 5-(2-aminopropyl)benzofuran
6-APB CH3 -O-CH=CH- 6-(2-aminopropyl)benzofuran
Short Name RN Rα Rβ R2 R3 R4 R5 Full Name

See also


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

[edit]Psychedelic tryptamines

α,N,N-TMT, 2,N,N-TMT, 5,N,N-TMT, 4-Acetoxy-DMT 4-Acetoxy-DET, 4-Acetoxy-DIPT, 4-HO-5-MeO-DMT, α-ET, α-MT, Baeocystin, Bufotenin, DET, DIPT, DMT, DPT, EIPT, Ethocin, Ethocybin, Miprocin, Iprocin, MET, MIPT, 5-Me-MIPT 5-MeO-α-ET, 5-MeO-α-MT, 5-MeO-DALT, 5-MeO-DET, 5-MeO-DIPT, 5-MeO-DMT, 5-MeO-DPT, 5-MeO-MIPT, 5-MeO-2,N,N-TMT, Norbaeocystin, Psilocin, Psilocybin


Template:TAAR ligands

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