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Substituted phenethylamine

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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

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.

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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