Substituted phenethylamine

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

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. Phenylethylamines are also generally found to be central nervous system stimulants with many also being entactogens/empathogens, and hallucinogens.

Structural classification

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. Several classes of substances can be considered phenylethylamine derivatives such as Substituted amphetamines, where there is a methyl group substituted at the alpha position on the ethyl chain, Substituted methylenedioxyphenethylamines, where a methylenedioxy group is joined at the 3 and 4 positions on the phenyl ring, and Substituted cathinones, which have a carbonyl group substituted at the beta position on the ethyl chain, most of which also have a methyl group substituted at the alpha positioning making most cathinones substituted amphetamines as well.

Pharmacology

Most 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 known mechanism of action or biological target that is common to all members of this subclass.

Examples

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 MDPV (Monkey Dust), MDMA (ecstasy), methamphetamine, and cathinone, are also members of the class. Many well-known prescription drugs are from the phenylethylamine class such as Adderall which uses Amphetamine, Desoxyn which uses methamphetamine, and Sudafed which uses pseudoephedrine.

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-isopropylphenethylamine 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-O-4OCH3(CH3)2CHOOCH32,5-Dimethoxy-4-propoxyphenethylamineHallucinogen, psychedelic and entheogenic[3]
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[4]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

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.

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 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.
  2. ↑ Wills B, Erickson T (9 March 2012). "Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives". In Barceloux DG (ed.). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Wiley. pp. 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.
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