Substituted phenethylamine

Substituted phenethylamine
Drug class
The structural formula of phenethylamine with marked substitution points. Phenethylamine is obtained when R^2=R^3=R^4=R^5=R^6=R^N=R^α=R^β=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 (NH₂) group via an ethyl (−CH₂–CH₂−) 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 aka DOM), entactogens (e.g., 3,4-methylenedioxyamphetamine aka 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. 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, 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.

List of substituted phenethylamines

Selected Phenethylamines

Short Name	R^N	R^α	R^β	R^2	R^3	R^4	R^5	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
Methamphetamine	CH3	CH3						N-methylamphetamine; N,α-dimethylphenethylamine	Monoamine releasing agent; Stimulant; dopaminergic neurotoxin
Phentermine		2CH3						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	Somewhat 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 pharmacodynamics 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
Selegiline	CH2CHCH				[]
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	Serotonergic Psychedelic
Proscaline					OCH3	OCH2CH2CH3	OCH3	2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine	Stimulant, entactogen and euphoriant
Metaescaline					OCH2CH3	OCH3	OCH3	2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine	Serotonergic Psychedelic, stimulant, entactogen and euphoriant
Allylescaline					OCH3	OCH2CH1CH2	OCH3	4-Allyloxy-3,5-dimethyloxyphenylethylamine	Stimulant, entactogen and euphoriant
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	R^2	R^3	R^4	R^5	Full Name	Biologic activity

Detection

method	Requirement
UV spectrometry	Reagent needed

See also

• Substituted amphetamines
• Substituted methylenedioxyphenethylamines
• Substituted cathinones
• Substituted phenylmorpholines
• 2Cs and DOx
• Substituted tryptamines

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