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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 class	; Substituted derivatives of phenethylamine
	In Wikidata

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., dl-2,5-dimethoxy-4-methylamphetamine a.k.a. DOM), entactogens (e.g., 3,4-methylenedioxyamphetamine a.k.a. 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.^{[medical citation needed]} 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]}

Numerous endogenous compounds – including hormones, monoamine neurotransmitters, and many trace amines (e.g., dopamine, norepinephrine, 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.

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List of substituted phenethylamines

Selected Phenethylamines
Short Name	R^N	R^α	R^β	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
meta-Octopamine			OH		OH			β,3-dihydroxyphenethylamine	Trace amine
para-Octopamine			OH			OH		β,4-dihydroxyphenethylamine	Trace aminergic α-adrenoceptor agonist
Phenylephrine	CH₃		OH		OH			β,3-dihydroxy-N-methylphenethylamine	α-adrenergic agonist; decongestant
6-Hydroxydopamine				OH		OH	OH	2,4,5-trihydroxyphenethylamine	neurotoxic agent for the dopamine and norepinephrine receptors
Salbutamol	C(CH₃)₃		OH			OH	CH₂OH	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
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
Bupropion	C(CH₃)₃	CH₃	=O		Cl			3-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
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
DOI		CH₃		OCH₃		I	OCH₃	2,5-dimethoxy-4-iodoamphetamine	Psychedelic
DON		CH₃		OCH₃		NO₂	OCH₃	2,5-dimethoxy-4-nitroamphetamine	Stimulant
DOC		CH₃		OCH₃		Cl	OCH₃	2,5-dimethoxy-4-chloroamphetamine	Psychedelic
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-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-F				OCH₃		F	OCH₃	2,5-dimethoxy-4-fluorophenethylamine	None
2C-N				OCH₃		NO₂	OCH₃	2,5-dimethoxy-4-nitrophenethylamine	euphoriant
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	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
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
25F-NBOMe	CH₂-C₆H₄-OCH₃			OCH₃		F	OCH₃	2-(4-fluoro-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
25I-NBOH	CH₂–C₆H₄–OH			OCH₃		I	OCH₃	N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine	Psychedelic
25C-NBOH	CH₂–C₆H₄–OH			OCH₃		Cl	OCH₃	N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine	Psychedelic
25B-NBOH	CH₂–C₆H₄–OH			OCH₃		Br	OCH₃	N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine	Psychedelic
25I-NBF	CH₂–C₆H₄–F			OCH₃		I	OCH₃	N-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine	Psychedelic
Amfepramone (diethylpropion)	C₂H₅, C₂H₅^{[note 2]}	CH₃	=O					N-diethyl-β-ketoamphetamine	Anorectic
Short Name	R^N	R^α	R^β	R²	R³	R⁴	R⁵	Full Name	Biologic activity

Detection

method	Requirement
UV spectrometry	Reagent needed

Notes

^ In other words, all of the compounds that belong to this class are structural analogs of phenethylamine.

^ Two ethyl groups attached to the amine group

References

[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

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101

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Rearuh

Substituted phenethylamine

Contents

List of substituted phenethylamines

Detection

See also

Notes

References

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Mononymous person

Substituted phenethylamine
Drug class
The structural formula of phenethylamine with marked substitution points. Phenethylamine is obtained when R²=R³=R⁴=R⁵=R⁶=R^N=R^α=R^β=H.
Class identifiers
Chemical class	Substituted derivatives of phenethylamine
In Wikidata