Substituted phenethylamine

The structure of substituted phenethylamines. Phenethylamine itself is obtained when R²=R³=R⁴=R⁵=R^N=R^α=R^β = H.

The substituted phenethylamines are chemical compounds with the 2-phenethylamine chemical structure modified at the phenyl ring, sidechain, and/or amino group. Some of them are psychoactive drugs, including stimulants, psychedelics, opioids, and entactogens, which exert their effects primarily through modulation of the monoamine neurotransmitter systems. Other substituted phenethylamines, such as dopamine and epinephrine are neurotransmitters. The substituted phenethylamines encompass the substituted amphetamines, the substituted methylenedioxyphenethylamines as well as a very large group of alkaloids derived from phenethylamines, including but by no means limited to tetrahydroisoquinolines, benzylisoquinolines, protoberberines, aporphines, morphinans, protopines and narcotine.^p. 74

Substituted phenethylamines fall into a wide variety of therapeutic classes, including but not limited to psychotropic drugs (including hallucinogens such as dl-2,5-dimethoxy-4-methylamphetamine a.k.a. DOM), central nervous system stimulants (e.g. amphetamine), appetite depressants (e.g. phentermine), antilipemic agents, vasoconstrictors (including nasal decongestants such as levomethamphetamine and pseudoephedrine), bronchodilators, cardiotonic agents, vasodilators, calcium channel blockers, antidepressants (e.g. bupropion, phenelzine, and tranylcypromine), neuroprotective agents and Antiparkinson agents.

Substituted phenethylamines are known to act as adrenergic agents (including adrenergic uptake inhibitors such as methamphetamine, adrenergic beta-agonists like methoxyphenamine and the adrenergic alpha-agonist mephentermine), antilipemic agents (e.g. benfluorex), dopamine agents (including dopamine uptake inhibitors such as bupropion), serotonin agents (including serotonin agonists such as 2,5-dimethoxy-4-bromoamphetamine and the serotonin uptake inhibitor fenfluramine), calcium channel blockers (e.g. prenylamine and verapamil) and monoamine oxidase inhibitors (e.g. selegiline).

List of substituted phenethylamines

Selected Phenethylamines

Short Name	RN	Rα	Rβ	R2	R3	R4	R5	Full Name
meta-Tyramine					OH			3-hydroxyphenethylamine
para-Tyramine						OH		4-hydroxyphenethylamine
Dopamine					OH	OH		3,4-dihydroxyphenethylamine
Epinephrine (Adrenaline)	CH3		OH		OH	OH		β,3,4-trihydroxy-N-methylphenethylamine
Norepinephrine (Noradrenaline)			OH		OH	OH		β,3,4-trihydroxyphenethylamine
meta-Octopamine			OH		OH			β,3-dihydroxyphenethylamine
para-Octopamine			OH			OH		β,4-dihydroxyphenethylamine
Phenylephrine	CH3		OH		OH			β,3-dihydroxy-N-methylphenethylamine
6-Hydroxydopamine				OH		OH	OH	2,4,5-trihydroxyphenethylamine
Salbutamol	C(CH3)3		OH			OH	CH2OH	β,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamine
β-Methylphenethylamine			CH3					β-methylphenethylamine
Amphetamine		CH3						α-methylphenethylamine
Methamphetamine	CH3	CH3						N-methylamphetamine
Methylphenidate	-CH2-CH2-CH2-CH2-	C(OCH3)=O					N,α-butylene-β-methoxycarbonylphenethylamine
Ephedrine / Pseudoephedrine	CH3	CH3	OH					N-methyl-β-hydroxyamphetamine
Cathine		CH3	OH					β-hydroxy-amphetamine
Cathinone		CH3	=O					β-keto-amphetamine
Methcathinone	CH3	CH3	=O					N-methylcathinone
Mephedrone	CH3	CH3	=O			CH3		4-methylmethcathinone
Ethcathinone	CH2CH3	CH3	=O					N-ethylcathinone
Bupropion	C(CH3)3	CH3	=O		Cl			3-chloro-N-tert-butyl-β-ketoamphetamine
Norfenfluramine		CH3			CF3			3-trifluoromethyl-amphetamine
Fenfluramine	CH2CH3	CH3			CF3			3-trifluoromethyl-N-ethyl-amphetamine
Phentermine		2CH3						α,α-dimethylphenethylamine
Mescaline					OCH3	OCH3	OCH3	3,4,5-trimethoxyphenethylamine
MDA		CH3			-O-CH2-O-		3,4-methylenedioxyamphetamine
MDEA	CH2CH3	CH3			-O-CH2-O-		3,4-methylenedioxy-N-ethylamphetamine
MDMA	CH3	CH3			-O-CH2-O-		3,4-methylenedioxy-N-methylamphetamine
MDMC	CH3	CH3	=O		-O-CH2-O-		3,4-methylenedioxymethcathinone
DOM		CH3		OCH3		CH3	OCH3	2,5-dimethoxy-4-methylamphetamine
DOB		CH3		OCH3		Br	OCH3	2,5-dimethoxy-4-bromoamphetamine
DOI		CH3		OCH3		I	OCH3	2,5-dimethoxy-4-iodoamphetamine
DON		CH3		OCH3		NO2	OCH3	2,5-dimethoxy-4-nitroamphetamine
DOC		CH3		OCH3		Cl	OCH3	2,5-dimethoxy-4-chloroamphetamine
2C-B				OCH3		Br	OCH3	2,5-dimethoxy-4-bromophenethylamine
2C-C				OCH3		Cl	OCH3	2,5-dimethoxy-4-chlorophenethylamine
2C-I				OCH3		I	OCH3	2,5-dimethoxy-4-iodophenethylamine
2C-D				OCH3		CH3	OCH3	2,5-dimethoxy-4-methylphenethylamine
2C-E				OCH3		CH2-CH3	OCH3	2,5-dimethoxy-4-ethylphenethylamine
2C-P				OCH3		CH2-CH3-CH3	OCH3	2,5-dimethoxy-4-propylphenethylamine
2C-F				OCH3		F	OCH3	2,5-dimethoxy-4-fluorophenethylamine
2C-N				OCH3		NO2	OCH3	2,5-dimethoxy-4-nitrophenethylamine
2C-T-2				OCH3		S-CH2CH3	OCH3	2,5-dimethoxy-4-ethylthio-phenethylamine
2C-T-4				OCH3		S-CH(CH3)2	OCH3	2,5-dimethoxy-4-isopropylthio-phenethylamine
2C-T-7				OCH3		S-CH2CH2CH3	OCH3	2,5-dimethoxy-4-propylthio-phenethylamine
2C-T-8				OCH3		S-CH2-C3H5	OCH3	2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine
2C-T-9				OCH3		S-C(CH3)3	OCH3	2,5-dimethoxy-4-tert-butylthio-phenethylamine
2C-T-21				OCH3		S-CH2-CH2-F	OCH3	2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine
Short Name	RN	Rα	Rβ	R2	R3	R4	R5	Full Name

See also

• Substituted amphetamines
• Substituted methylenedioxyphenethylamines
• Substituted cathinones
• 2Cs
• DOx