Substituted 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.

Substituted phenethylamine
Drug class
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 classSubstituted derivatives of phenethylamine
Legal status
In Wikidata

The structural formula of any substituted phenethylamine contains a phenyl ring that is joined to an 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 psychoactive drugs which belong to a variety of different drug classes, including central nervous system stimulants (e.g., amphetamine), hallucinogens (e.g., 3,4,5-trimethoxyphenethylamine a.k.a. mescaline), 2,5-dimethoxy-4-methylamphetamine a.k.a. DOM), entactogen (e.g. 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.[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.

Numerous endogenous compounds – including hormones, catecholamines such as dopamine and noradrenaline, and many trace amines (e.g. 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
Chemical

Structure

 Short Name RN Rα Rβ R2 R3 R4 R5 Full Name Biologic activity
meta-TyramineOH3-hydroxyphenethylamineTrace amine
para-TyramineOH4-hydroxyphenethylamineTrace amine
DopamineOHOH3,4-dihydroxyphenethylamineCatecholamine neurotransmitter
Epinephrine (Adrenaline)CH3OHOHOHβ,3,4-trihydroxy-N-methylphenethylamineCatecholamine neurotransmitter/Fight or Flight hormone
Norepinephrine (Noradrenaline)OHOHOHβ,3,4-trihydroxyphenethylamineCatecholamine neurotransmitter/Fight or Flight hormone
NorfenefrineOHOHβ,3-dihydroxyphenethylamineTrace amine
para-OctopamineOHOHβ,4-dihydroxyphenethylamineTrace aminergic α-adrenoceptor agonist
OxidopamineOHOHOH2,4,5-trihydroxyphenethylamineneurotoxic agent for the dopamine and norepinephrine receptors
PhenylephrineCH3OHOHβ,3-dihydroxy-N-methylphenethylamineα-adrenergic agonist; decongestant
Isoprenaline CH(CH3)2 OH OH OH β,3-dihydroxy-N-methylphenethylamine β-adrenergic agonist; decongestant
SalbutamolC(CH3)3OHCH2OHOHβ,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamineShort-action β2-adrenergic agonist
β-MethylphenethylamineCH3β-methylphenethylamineStimulant
AmphetamineCH3α-methylphenethylamineMonoamine releasing agent; Stimulant
N-MethylphenethylamineCH3N-methylphenethylamineTrace amine; endogenous amphetamine isomer
N,N-Dimethylphenethylamine(CH3)2N,N-dimethylphenethylamineTrivial effects (used as a food additive and flavoring agent)
MethamphetamineCH3CH3N-methylamphetamine; N,α-dimethylphenethylamineMonoamine releasing agent; stimulant; neurotoxin
Phentermine(CH3)2α-methylamphetamine; α,α-dimethylphenethylamineStimulant, anorectic
OrtetamineCH3CH32-methylamphetamine; 2,α-dimethylphenethylamineStimulant, 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)=ON,α-butylene-β-methoxycarbonylphenethylamineNDRI; Stimulant
Ephedrine / PseudoephedrineCH3CH3OHN-methyl-β-hydroxyamphetamineReleasing agent; stimulant; decongestant
CathineCH3OHd-β-hydroxyamphetamineModerately selective norepinephrine releasing agent
CathinoneCH3=Oβ-ketoamphetamineSelective norepinephrine and dopamine releasing agent
MethcathinoneCH3CH3=ON-methylcathinoneSelective norepinephrine and dopamine releasing agent
MephedroneCH3CH3=OCH34-methylmethcathinoneStimulant, unknown pharmacodynamic actions
EthcathinoneCH2CH3CH3=ON-ethylcathinoneStimulant and norepinephrine releasing agent
Amfepramone (diethylpropion)C2H5, C2H5[note 2]CH3=ON-diethyl-β-ketoamphetamineAnorectic
BupropionC(CH3)3CH3=OCl5-chloro-N-tert-butyl-β-ketoamphetamineNDRI
NorfenfluramineCH3CF33-trifluoromethyl-amphetamineSSRA
FenfluramineCH2CH3CH3CF33-trifluoromethyl-N-ethylamphetamineSSRA
5-APBCH3-CH=CH-O-5-(2-aminopropyl)benzofuranStimulant, entactogen
6-APBCH3-O-CH=CH-6-(2-aminopropyl)benzofuranStimulant, entactogen
MDACH3-O-CH2-O-3,4-methylenedioxy-amphetamineStimulant, psychedelic, entactogen
MDEACH2CH3CH3-O-CH2-O-3,4-methylenedioxy-N-ethylamphetaminePsychedelic, entactogen, and releasing agent
MDMACH3CH3-O-CH2-O-3,4-methylenedioxy-N-methylamphetaminePsychedelic, entactogen, and releasing agent
MDMCCH3CH3=O-O-CH2-O-3,4-methylenedioxymethcathinonePsychedelic, entactogen, and releasing agent
MMDACH3-O-CH2-O-OCH35-methoxy-3,4-methylenedioxy-amphetamineStimulant, psychedelic and entactogen
MMDMACH3CH3-O-CH2-O-OCH35-methoxy-3,4-methylenedioxy-N-methylamphetaminePsychedelic, entactogen, and releasing agent
Lophophine-O-CH2-O-OCH35-methoxy-3,4-methylenedioxyphenethylaminePsychedelic and entactogen
MescalineOCH3OCH3OCH33,4,5-trimethoxyphenethylaminePsychedelic and entactogen
ProscalineOCH3OCH2CH2CH3OCH32-(3,5-dimethoxy-4-propoxyphenyl)ethanaminePsychedelic and entactogen
MetaescalineOCH2CH3OCH3OCH32-(3-ethoxy-4,5-dimethoxyphenyl)ethanaminePsychedelic and entactogen
AllylescalineOCH3OCH2CH1CH2OCH34-Allyloxy-3,5-dimethyloxyphenylethylaminePsychedelic and entactogen
MethallylescalineOCH3OCH2C(CH2CH3)OCH34-Methallyloxy-3,5-dimethoxyphenethylaminePsychedelic and entactogen
AsymbescalineOCH2CH3OCH2CH3OCH33,4-Diethoxy-5-methoxyphenethylaminePsychedelic and euphoriant
DOMCH3OCH3CH3OCH32,5-dimethoxy-4-methylamphetaminePsychedelic
DOBCH3OCH3BrOCH32,5-dimethoxy-4-bromoamphetaminePsychedelic
DOCCH3OCH3ClOCH32,5-dimethoxy-4-chloroamphetaminePsychedelic
DOICH3OCH3IOCH32,5-dimethoxy-4-iodoamphetaminePsychedelic
DONCH3OCH3NO2OCH32,5-dimethoxy-4-nitroamphetamineStimulant
2C-BOCH3BrOCH32,5-dimethoxy-4-bromophenethylaminePsychedelic, stimulant, entactogen and euphoriant
βk-2C-B=OOCH3BrOCH32,5-dimethoxy-4-bromo-β-ketophenethylaminePsychedelic, stimulant, entactogen and euphoriant
2C-COCH3ClOCH32,5-dimethoxy-4-chlorophenethylaminePsychedelic
2C-FOCH3FOCH32,5-dimethoxy-4-fluorophenethylaminePsychedelic
2C-IOCH3IOCH32,5-dimethoxy-4-iodophenethylaminePsychedelic, stimulant
2C-DOCH3CH3OCH32,5-dimethoxy-4-methylphenethylaminePsychedelic, stimulant
2C-EOCH3CH2-CH3OCH32,5-dimethoxy-4-ethylphenethylaminePsychedelic
2C-POCH3CH2-CH3-CH3OCH32,5-dimethoxy-4-propylphenethylamineEntactogen, euphoriant and Psychedelic
2C-NOCH3NO2OCH32,5-dimethoxy-4-nitrophenethylamineeuphoriant
2C-T-2OCH3S-CH2CH3OCH32,5-dimethoxy-4-ethylthio-phenethylaminePsychedelic
2C-T-4OCH3S-CH(CH3)2OCH32,5-dimethoxy-4-isopropylthio-phenethylaminePsychedelic
2C-T-7OCH3S-CH2CH2CH3OCH32,5-dimethoxy-4-propylthio-phenethylaminePsychedelic
2C-T-8OCH3S-CH2-C3H5OCH32,5-dimethoxy-4-cyclopropylmethylthio-phenethylaminePsychedelic
2C-T-19OCH3S-C(CH3)3OCH32,5-dimethoxy-4-tert-butylthio-phenethylaminePsychedelic
2C-T-21OCH3S-CH2-CH2-FOCH32,5-dimethoxy-4-(2-fluoroethylthio)-phenethylaminePsychedelic and euphoriant
25B-NBOMe[3]CH2-C6H4-OCH3OCH3BrOCH32-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanaminePsychedelic
25C-NBOMeCH2-C6H4-OCH3OCH3ClOCH32-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanaminePsychedelic
25F-NBOMeCH2-C6H4-OCH3OCH3FOCH32-(4-fluoro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanaminePsychedelic
25I-NBOMeCH2-C6H4-OCH3OCH3IOCH32-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanaminePsychedelic
25D-NBOMeCH2-C6H4-OCH3OCH3CH2OCH32-(4-methyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanaminePsychedelic
25E-NBOMeCH2-C6H4-OCH3OCH3CH2-CH3OCH32-(4-ethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanaminePsychedelic
25P-NBOMeCH2-C6H4-OCH3OCH3CH2-CH3-CH3OCH32-(4-propyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanaminePsychedelic
Mescaline-NBOMeCH2-C6H4-OCH3OCH3OCH3OCH3N-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanaminePsychedelic
25B-NBOHCH2–C6H4–OHOCH3BrOCH3N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylaminePsychedelic
25C-NBOHCH2–C6H4–OHOCH3ClOCH3N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylaminePsychedelic
25I-NBOHCH2–C6H4–OHOCH3IOCH3N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylaminePsychedelic
25I-NBFCH2–C6H4–FOCH3IOCH3N-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylaminePsychedelic
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. Inan, Funda; Brunt, Tibor M.; Contrucci, Ramon R.; Hondebrink, Laura; Franssen, Eric J. F. (2020). "Novel Phenethylamines and Their Potential Interactions With Prescription Drugs: A Systematic Critical Review". Therapeutic Drug Monitoring. 42 (2): 271–281. doi:10.1097/ftd.0000000000000725. ISSN 0163-4356. PMID 32022784. S2CID 211035606.
  2. Wills, Brandon; Erickson, Timothy (2 February 2012). "Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives". Medical Toxicology of Drug Abuse: 156–192. doi:10.1002/9781118105955.ch10. ISBN 978-0-471-72760-6.
  3. Custodio, Raly James Perez; Sayson, Leandro Val; Botanas, Chrislean Jun; Abiero, Arvie; You, Kyung Yi; Kim, Mikyung; Lee, Hyun Jun; Yoo, Sung Yeun; Lee, Kun Won; Lee, Yong Sup; Seo, Joung-Wook (2019). "25B-NBOMe, a novel N-2-methoxybenzyl-phenethylamine (NBOMe) derivative, may induce rewarding and reinforcing effects via a dopaminergic mechanism: Evidence of abuse potential". Addiction Biology. 25 (6): e12850. doi:10.1111/adb.12850. ISSN 1369-1600. PMID 31749223. S2CID 208217863.
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