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Substituted phenethylamine

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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
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
Legal status
In Wikidata

Structural classification

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The structure of the parent phenethylamine

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.

Pharmacology

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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.[medical citation needed]

Examples

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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

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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 Trace aminergic 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-isopropylphenethylamine 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 Stimulant, entactogen
  6-APB CH3 -O-CH=CH- 6-(2-aminopropyl)benzofuran Stimulant, entactogen
  MDA CH3 -O-CH2-O- 3,4-methylenedioxy-amphetamine 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
  MMDA CH3 -O-CH2-O- OCH3 5-methoxy-3,4-methylenedioxy-amphetamine Stimulant, psychedelic and entactogen
  MMDMA CH3 CH3 -O-CH2-O- OCH3 5-methoxy-3,4-methylenedioxy-N-methylamphetamine Psychedelic, entactogen, and releasing agent
  Lophophine -O-CH2-O- OCH3 5-methoxy-3,4-methylenedioxyphenethylamine Psychedelic and entactogen
  Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxyphenethylamine Psychedelic and entactogen
  Proscaline OCH3 OCH2CH2CH3 OCH3 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine Psychedelic and entactogen
  Metaescaline OCH2CH3 OCH3 OCH3 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine Psychedelic and entactogen
  Allylescaline OCH3 OCH2CH1CH2 OCH3 4-Allyloxy-3,5-dimethyloxyphenylethylamine Psychedelic and entactogen
  Methallylescaline OCH3 OCH2C(CH2CH3) OCH3 4-Methallyloxy-3,5-dimethoxyphenethylamine Psychedelic and entactogen
  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
  DOC CH3 OCH3 Cl OCH3 2,5-dimethoxy-4-chloroamphetamine 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 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-F OCH3 F OCH3 2,5-dimethoxy-4-fluorophenethylamine 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-N OCH3 NO2 OCH3 2,5-dimethoxy-4-nitrophenethylamine euphoriant
  2C-O-4 OCH3 (CH3)2CHO OCH3 2,5-Dimethoxy-4-propoxyphenethylamine Hallucinogen, psychedelic and entheogenic[3]
  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-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 Psychedelic and euphoriant
  25B-NBOMe[4] 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

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Method Requirement
UV spectrometry Reagent needed

Detection of substituted phenethylamines, which include compounds such as 2C-B, MDMA, and other designer drugs, involves various analytical methods aimed at identifying these psychoactive substances. These compounds are structurally similar to amphetamines, making their detection challenging due to potential cross-reactivity in standard drug tests. Techniques like gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS), and immunoassay screenings are commonly employed for accurate identification. Advanced methods like high-performance liquid chromatography (HPLC) allow for precise separation and quantification of these substances even at low concentrations. Given the rising use of these drugs in recreational settings, developing sensitive and specific detection techniques remains crucial in forensic toxicology and clinical diagnostics.[5]

See also

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Notes

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  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

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  1. ^ Inan F, Brunt TM, Contrucci RR, Hondebrink L, Franssen EJ (April 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. PMID 32022784. S2CID 211035606.
  2. ^ Wills B, Erickson T (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. ^ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 2C-O-4 Entry in PiHKAL
  4. ^ Custodio RJ, Sayson LV, Botanas CJ, Abiero A, You KY, Kim M, et al. (November 2020). "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. PMID 31749223. S2CID 208217863.
  5. ^ "Substituted Phenethylamine - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 27 August 2024.
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