Substituted phenethylamine

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Substituted phenethylamine
Chemical class
Substituted derivatives of phenethylamine
Legal status
In Wikidata
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

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

vasopressors (e.g., ephedrine), among others.[1][2] 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.[medical citation needed
]

Numerous

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
Chemical

Structure

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
Norfenefrine OH OH β,3-dihydroxyphenethylamine Trace amine
para-Octopamine OH OH β,4-dihydroxyphenethylamine
α-adrenoceptor
agonist
Oxidopamine
 OH OH OH 2,4,5-trihydroxyphenethylamine neurotoxic agent for the dopamine and norepinephrine receptors
Phenylephrine CH3 OH OH β,3-dihydroxy-N-methylphenethylamine α-adrenergic agonist; decongestant
Isoprenaline
 CH(CH3)2 OH OH OH β,3-dihydroxy-N-methylphenethylamine β-adrenergic agonist; decongestant
Salbutamol C(CH3)3 OH CH2OH OH 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
N,N-Dimethylphenethylamine (CH3)2 N,N-dimethylphenethylamine Trivial effects (used as a food additive and flavoring agent)
Methamphetamine CH3 CH3 N-methylamphetamine; N,α-dimethylphenethylamine Monoamine releasing agent; stimulant; neurotoxin
Phentermine (CH3)2 α-methylamphetamine; α,α-dimethylphenethylamine Stimulant, anorectic
Ortetamine CH3 CH3 2-methylamphetamine; 2,α-dimethylphenethylamine Stimulant, anorectic
Phenelzine NH2 β-phenylethylhydrazine Monoamine oxidase inhibitor
Tranylcypromine -CH2- 2-phenylcyclopropylamine Monoamine oxidase inhibitor
Selegiline -CH2-C≡CH CH3 N,α-dimethyl-N-2-propynylphenethylamine
MAO-B selective monoamine oxidase inhibitor
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 Moderately 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 pharmacodynamic actions
Ethcathinone CH2CH3 CH3 =O N-ethylcathinone Stimulant and norepinephrine releasing agent
Amfepramone (diethylpropion) C2H5, C2H5[note 2] CH3 =O N-diethyl-β-ketoamphetamine Anorectic
Bupropion C(CH3)3 CH3 =O Cl 5-
chloro
-N-tert-butyl-β-ketoamphetamine		 NDRI
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
entactogen
6-APB
 CH3 -O-CH=CH- 6-(2-aminopropyl)benzofuran
entactogen
MDA
 CH3 -O-CH2-O- 3,4-methylenedioxy-amphetamine
entactogen
MDEA
 CH2CH3 CH3 -O-CH2-O- 3,4-methylenedioxy-N-ethylamphetamine
releasing agent
MDMA CH3 CH3 -O-CH2-O- 3,4-methylenedioxy-N-methylamphetamine
releasing agent
MDMC
 CH3 CH3 =O -O-CH2-O- 3,4-methylenedioxymethcathinone
releasing agent
MMDA CH3 -O-CH2-O- OCH3 5-methoxy-3,4-methylenedioxy-amphetamine
entactogen
MMDMA CH3 CH3 -O-CH2-O- OCH3 5-methoxy-3,4-methylenedioxy-N-methylamphetamine
releasing agent
Lophophine -O-CH2-O- OCH3 5-methoxy-3,4-methylenedioxyphenethylamine
entactogen
Mescaline
OCH3
 OCH3 OCH3 3,4,5-tri
methoxy
phenethylamine
entactogen
Proscaline OCH3 OCH2CH2CH3 OCH3 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine
entactogen
Metaescaline
OCH2CH3
 OCH3 OCH3 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine
entactogen
Allylescaline OCH3 OCH2CH1CH2 OCH3 4-Allyloxy-3,5-dimethyloxyphenylethylamine
entactogen
Methallylescaline OCH3 OCH2C(CH2CH3) OCH3 4-Methallyloxy-3,5-dimethoxyphenethylamine
entactogen
Asymbescaline OCH2CH3 OCH2CH3 OCH3 3,4-Diethoxy-5-methoxyphenethylamine
euphoriant
DOM
 CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methylamphetamine Psychedelic
DOB
 CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromoamphetamine Psychedelic
DOC
 CH3 OCH3 Cl OCH3 2,5-dimethoxy-4-
chloro
amphetamine		 Psychedelic
DOI
 CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodoamphetamine Psychedelic
DON
 CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitroamphetamine Stimulant
2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromophenethylamine
euphoriant
βk-2C-B =O OCH3 Br OCH3 2,5-dimethoxy-4-bromo-β-ketophenethylamine
euphoriant
2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chlorophenethylamine Psychedelic
2C-F OCH3 F OCH3 2,5-dimethoxy-4-
fluoro
phenethylamine		 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
euphoriant
and Psychedelic
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-
isopropyl
thio-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-
cyclopropyl
methylthio-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
euphoriant
25B-NBOMe[3] 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
25F-NBOMe CH2-C6H4-OCH3 OCH3 F OCH3 2-(4-fluoro-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
Mescaline-NBOMe
 CH2-C6H4-OCH3
OCH3
 OCH3 OCH3 N-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanamine Psychedelic
25B-NBOH CH2–C6H4–OH OCH3 Br OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine Psychedelic
25C-NBOH CH2–C6H4–OH OCH3 Cl OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine Psychedelic
25I-NBOH CH2–C6H4–OH OCH3 I OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine Psychedelic
25I-NBF CH2–C6H4–F OCH3 I OCH3 N-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine Psychedelic
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

  1. S2CID 211035606
    .
  2. ISBN 978-0-471-72760-6
    .
  3. S2CID 208217863
    .
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