Category:Phenethylamine

Substitutive structure of a *phenethylamine* molecule.

Substituted phenethylamine refers to a class of compounds which typically produce strong psychedelic effects.

Chemistry

Phenethylamine comprises a benzene ring attached to a mono-amine group via an ethyl side-chain. Hydrogen atoms around the structure can be substituted for other functional groups to produce drugs of varying potency, efficacy and half-life.

Phenethylamines, tabulated by structure (from Wikipedia)

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-methylphenethylamin	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	Endogenous amphetamine isomer; Trace amine
Methamphetamine	CH₃	CH₃						N-methylamphetamine	Monoamine releasing agent; Stimulant; dopaminergic neurotoxin
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
Norfenfluramine		CH₃			CF₃			3-trifluoromethyl-amphetamine	SSRA
Fenfluramine	CH₂CH₃	CH₃			CF₃			3-trifluoromethyl-N-ethyl-amphetamine	SSRA
Phentermine		2CH₃						α,α-dimethylphenethylamine	Stimulant, anorectic
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-methylenedioxyamphetamine	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-9				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
Short Name	R^N	R^α	R^β	R²	R³	R⁴	R⁵	Full Name

Pharmacology

Phenethylamines are believed to produce their psychedelic effect primarily by partial agonism of 5-HT_2A receptors.

Several neurotransmitters are derived from phenethylamine, such as:

Subcategories

This category has the following 6 subcategories, out of 6 total.

2

2C-x

A

L

Lysergamide

P

Phenylmorpholine

Pages in category "Phenethylamine"

The following 22 pages are in this category, out of 22 total.

Category:Phenethylamine

Chemistry

Pharmacology

Subcategories

2

A

L

P

Pages in category "Phenethylamine"

*

A

B

E

F

M

O

P

R

T

Β