Chemistry:Substituted phenethylamine

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Short description: Chemical class of organic compounds
Substituted phenethylamine
Drug class
Phenethylamine structure diagram
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
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 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-Tyramine.svg meta-Tyramine OH 3-hydroxyphenethylamine Trace amine
Tyramine.svg para-Tyramine OH 4-hydroxyphenethylamine Trace amine
Dopamine.svg Dopamine OH OH 3,4-dihydroxyphenethylamine Catecholamine neurotransmitter
Epinephrine.svg Epinephrine (Adrenaline) CH3 OH OH OH β,3,4-trihydroxy-N-methylphenethylamine Catecholamine neurotransmitter/Fight or Flight hormone
Norepinephrine.svg Norepinephrine (Noradrenaline) OH OH OH β,3,4-trihydroxyphenethylamine Catecholamine neurotransmitter/Fight or Flight hormone
Norfenefrine.png Norfenefrine OH OH β,3-dihydroxyphenethylamine Trace amine
Octapamine.svg para-Octopamine OH OH β,4-dihydroxyphenethylamine Trace aminergic α-adrenoceptor agonist
6-Hydroxydopamine.svg Oxidopamine OH OH OH 2,4,5-trihydroxyphenethylamine neurotoxic agent for the dopamine and norepinephrine receptors
Phenylephrine.png Phenylephrine CH3 OH OH β,3-dihydroxy-N-methylphenethylamine α-adrenergic agonist; decongestant
Isoprenaline.svg Isoprenaline CH(CH3)2 OH OH OH β,3-dihydroxy-N-methylphenethylamine β-adrenergic agonist; decongestant
Salbutamol.svg Salbutamol C(CH3)3 OH CH2OH OH β,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamine Short-action β2-adrenergic agonist
Beta-methylphenethylamine.png β-Methylphenethylamine CH3 β-methylphenethylamine Stimulant
Amphetamine.svg Amphetamine CH3 α-methylphenethylamine Monoamine releasing agent; Stimulant
Methylphenethylamine.png N-Methylphenethylamine CH3 N-methylphenethylamine Trace amine; endogenous amphetamine isomer
N,N-Dimethylphenethylamine.svg N,N-Dimethylphenethylamine (CH3)2 N,N-dimethylphenethylamine Trivial effects (used as a food additive and flavoring agent)
Methamphetamine.svg Methamphetamine CH3 CH3 N-methylamphetamine; N,α-dimethylphenethylamine Monoamine releasing agent; stimulant; neurotoxin
Fentermina.svg Phentermine (CH3)2 α-methylamphetamine; α,α-dimethylphenethylamine Stimulant, anorectic
2-methylamphetamine.svg Ortetamine CH3 CH3 2-methylamphetamine; 2,α-dimethylphenethylamine Stimulant, anorectic
Phenelzine.svg Phenelzine NH2 β-phenylethylhydrazine Monoamine oxidase inhibitor
Tranylcypromine Structure.svg Tranylcypromine -CH2- 2-phenylcyclopropylamine Monoamine oxidase inhibitor
Selegiline.svg Selegiline -CH2-C≡CH CH3 N,α-dimethyl-N-2-propynylphenethylamine MAO-B selective monoamine oxidase inhibitor
Methylphenidate-2D-skeletal.svg Methylphenidate -CH2-CH2-CH2-CH2- C(OCH3)=O N,α-butylene-β-methoxycarbonylphenethylamine NDRI; Stimulant
Ephedrine-ifa.png Ephedrine / Pseudoephedrine CH3 CH3 OH N-methyl-β-hydroxyamphetamine Releasing agent; stimulant; decongestant
Pseudonorephedrine.png Cathine CH3 OH d-β-hydroxyamphetamine Moderately selective norepinephrine releasing agent
Cathinone.svg Cathinone CH3 =O β-ketoamphetamine Selective norepinephrine and dopamine releasing agent
Methcathinone skeletal.svg Methcathinone CH3 CH3 =O N-methylcathinone Selective norepinephrine and dopamine releasing agent
Mephedrone-2D-skeletal.svg Mephedrone CH3 CH3 =O CH3 4-methylmethcathinone Stimulant, unknown pharmacodynamic actions
Ethcathinone.svg Ethcathinone CH2CH3 CH3 =O N-ethylcathinone Stimulant and norepinephrine releasing agent
Amfepramone.svg Amfepramone (diethylpropion) C2H5, C2H5[note 2] CH3 =O N-diethyl-β-ketoamphetamine Anorectic
Bupropion 1.svg Bupropion C(CH3)3 CH3 =O Cl 5-chloro-N-tert-butyl-β-ketoamphetamine NDRI
3-trifluoromethylamphetamine.svg Norfenfluramine CH3 CF3 3-trifluoromethyl-amphetamine SSRA
Fenfluramine2DCSD.svg Fenfluramine CH2CH3 CH3 CF3 3-trifluoromethyl-N-ethylamphetamine SSRA
5APB.svg 5-APB CH3 -CH=CH-O- 5-(2-aminopropyl)benzofuran Stimulant, entactogen
6APB.svg 6-APB CH3 -O-CH=CH- 6-(2-aminopropyl)benzofuran Stimulant, entactogen
MDA-2D-skeletal.svg MDA CH3 -O-CH2-O- 3,4-methylenedioxy-amphetamine Stimulant, psychedelic, entactogen
MDEA.svg MDEA CH2CH3 CH3 -O-CH2-O- 3,4-methylenedioxy-N-ethylamphetamine Psychedelic, entactogen, and releasing agent
MDMA (simple).svg MDMA CH3 CH3 -O-CH2-O- 3,4-methylenedioxy-N-methylamphetamine Psychedelic, entactogen, and releasing agent
MDMC.svg MDMC CH3 CH3 =O -O-CH2-O- 3,4-methylenedioxymethcathinone Psychedelic, entactogen, and releasing agent
MMDA-structure.png MMDA CH3 -O-CH2-O- OCH3 5-methoxy-3,4-methylenedioxy-amphetamine Stimulant, psychedelic and entactogen
MMDMA-structure.png MMDMA CH3 CH3 -O-CH2-O- OCH3 5-methoxy-3,4-methylenedioxy-N-methylamphetamine Psychedelic, entactogen, and releasing agent
Lophophine.png Lophophine -O-CH2-O- OCH3 5-methoxy-3,4-methylenedioxyphenethylamine Psychedelic and entactogen
Mescaline Structural Formulae bondline.svg Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxyphenethylamine Psychedelic and entactogen
Proscaline.svg Proscaline OCH3 OCH2CH2CH3 OCH3 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine Psychedelic and entactogen
Metaescaline.svg Metaescaline OCH2CH3 OCH3 OCH3 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine Psychedelic and entactogen
Allylescaline.svg Allylescaline OCH3 OCH2CH1CH2 OCH3 4-Allyloxy-3,5-dimethyloxyphenylethylamine Psychedelic and entactogen
Methallylescaline.svg Methallylescaline OCH3 OCH2C(CH2CH3) OCH3 4-Methallyloxy-3,5-dimethoxyphenethylamine Psychedelic and entactogen
Asymbescaline.png Asymbescaline OCH2CH3 OCH2CH3 OCH3 3,4-Diethoxy-5-methoxyphenethylamine Psychedelic and euphoriant
2,5-dimethoxy-4-methylamphetamine.svg DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methylamphetamine Psychedelic
2,5-dimethoxy-4-bromoamphetamine.svg DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromoamphetamine Psychedelic
2,5-dimethoxy-4-chloroamphetamine.svg DOC CH3 OCH3 Cl OCH3 2,5-dimethoxy-4-chloroamphetamine Psychedelic
2,5-dimethoxy-4-iodoamphetamine.svg DOI CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodoamphetamine Psychedelic
2,5-dimethoxy-4-nitroamphetamine.svg DON CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitroamphetamine Stimulant
2C-B-Chemdraw.png 2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromophenethylamine Psychedelic, stimulant, entactogen and euphoriant
Βk-2C-B.svg βk-2C-B =O OCH3 Br OCH3 2,5-dimethoxy-4-bromo-β-ketophenethylamine Psychedelic, stimulant, entactogen and euphoriant
2C-C-Chemdraw.png 2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chlorophenethylamine Psychedelic
2C-F-Chemdraw.png 2C-F OCH3 F OCH3 2,5-dimethoxy-4-fluorophenethylamine Psychedelic
2C-I-Chemdraw.png 2C-I OCH3 I OCH3 2,5-dimethoxy-4-iodophenethylamine Psychedelic, stimulant
2C-D-Chemdraw.png 2C-D OCH3 CH3 OCH3 2,5-dimethoxy-4-methylphenethylamine Psychedelic, stimulant
2C-E-Chemdraw.png 2C-E OCH3 CH2-CH3 OCH3 2,5-dimethoxy-4-ethylphenethylamine Psychedelic
2C-P-Chemdraw.png 2C-P OCH3 CH2-CH3-CH3 OCH3 2,5-dimethoxy-4-propylphenethylamine Entactogen, euphoriant and Psychedelic
2C-N 2DACS.svg 2C-N OCH3 NO2 OCH3 2,5-dimethoxy-4-nitrophenethylamine euphoriant
2C-T-2-Chemdraw.png 2C-T-2 OCH3 S-CH2CH3 OCH3 2,5-dimethoxy-4-ethylthio-phenethylamine Psychedelic
2C-T-4-Chemdraw.png 2C-T-4 OCH3 S-CH(CH3)2 OCH3 2,5-dimethoxy-4-isopropylthio-phenethylamine Psychedelic
2C-T-7-Chemdraw.png 2C-T-7 OCH3 S-CH2CH2CH3 OCH3 2,5-dimethoxy-4-propylthio-phenethylamine Psychedelic
2C-T-8-Chemdraw.png 2C-T-8 OCH3 S-CH2-C3H5 OCH3 2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine Psychedelic
2C-T-19.png 2C-T-19 OCH3 S-C(CH3)3 OCH3 2,5-dimethoxy-4-tert-butylthio-phenethylamine Psychedelic
2C-T-21-Chemdraw.png 2C-T-21 OCH3 S-CH2-CH2-F OCH3 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine Psychedelic and euphoriant
2C-B-NBOMe-skeletal.svg 25B-NBOMe[3] CH2-C6H4-OCH3 OCH3 Br OCH3 2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
2C-C-NBOMe-skeletal.svg 25C-NBOMe CH2-C6H4-OCH3 OCH3 Cl OCH3 2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25F-NBOMe structure.png 25F-NBOMe CH2-C6H4-OCH3 OCH3 F OCH3 2-(4-fluoro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
2C-I-NBOMe-skeletal.svg 25I-NBOMe CH2-C6H4-OCH3 OCH3 I OCH3 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25D-NBOMe2DACS.svg 25D-NBOMe CH2-C6H4-OCH3 OCH3 CH2 OCH3 2-(4-methyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
2C-E-NBOMe 2DACS.svg 25E-NBOMe CH2-C6H4-OCH3 OCH3 CH2-CH3 OCH3 2-(4-ethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25P-NBOMe.svg 25P-NBOMe CH2-C6H4-OCH3 OCH3 CH2-CH3-CH3 OCH3 2-(4-propyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
Mescaline-NBOMe.svg Mescaline-NBOMe CH2-C6H4-OCH3 OCH3 OCH3 OCH3 N-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanamine Psychedelic
25B-NBOH structure.png 25B-NBOH CH2–C6H4–OH OCH3 Br OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine Psychedelic
NBOH-2CC structure.png 25C-NBOH CH2–C6H4–OH OCH3 Cl OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine Psychedelic
2C-I-NBOH-skeletal.svg 25I-NBOH CH2–C6H4–OH OCH3 I OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine Psychedelic
25i-NBF.svg 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. ↑ 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. http://dx.doi.org/10.1097/ftd.0000000000000725. 
  2. ↑ Wills, Brandon; Erickson, Timothy (2012-02-02). "Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives". Medical Toxicology of Drug Abuse: 156–192. doi:10.1002/9781118105955.ch10. http://dx.doi.org/10.1002/9781118105955.ch10. 
  3. ↑ Custodio, Raly James Perez; Sayson, Leandro Val; Botanas, Chrislean Jun; Abiero, Arvie; You, Kyung Yi; Kim, Mikyung; Lee, Hyun Jun; Yoo, Sung Yeun et al. (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" (in en). Addiction Biology 25 (6): e12850. doi:10.1111/adb.12850. ISSN 1369-1600. PMID 31749223. 



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