Phenylethylamines

The parent compound of phenylethylamines, phenylethylamine

General structural formula of the phenylethylamines with the basic structure marked in blue .

As Phenylethylamine (also phenylalkylamines or β-phenylalkylamines ) refers to a group of chemical compounds which are derived from phenylethylamine derived. Many phenylethylamines are found widely in nature (e.g. tyramine and dopamine ), while others are of artificial origin (e.g. amphetamine ).

Naturally occurring phenylethylamines, for example as L - amino acids ( L - tyrosine and L - phenylalanine ), are of fundamental importance for life . In the human and animal organism, phenylethylamines also play an important role as neurotransmitters (e.g. dopamine ) and hormones (e.g. adrenaline ). Many alkaloids occurring in the plant kingdom can also be assigned to the phenylethylamines (e.g. ephedrine , mescaline ).

Synthetically produced phenylethylamines, such as. B. the calcium antagonist verapamil or etilefrine are used as drugs . Numerous compounds in this group of substances have psychotropic properties.

Phenylethylamines

• Phenethylamine (PEA)
• 4-hydroxyphenylethylamine ( tyramine )
• 1- (3-hydroxyphenyl) -2- (ethylamino) ethanol ( etilefrine )
• 1- (4-hydroxyphenyl) -2- (methylamino) ethanol ( synephrine )
• 4- (2-amino-1-hydroxy-ethyl) phenol ( norsynephrine )
• Methylphenidate (MPH; trade name including Ritalin)

Catecholamines

→ Main article : Catecholamines

• adrenaline
• Norepinephrine
• Dopamine (3,4-dihydroxy- β- phenylethylamine)
• Isoprenaline
• Orciprenaline
• Dobutamine
• Reproterol
• Terbutaline
• Dopexamine
• Metanephrine

Methoxyphenylethylamine

• Venlafaxine

2,5-dimethoxyphenylethylamine

→ Main article : 2C (group of substances)

• 2,5-dimethoxy-4-bromophenethylamine (2C-B)
• 2,5-dimethoxy-4-chlorophenethylamine (2C-C)
• 2,5-dimethoxy-4-methylphenylethylamine (2C-D)
• 2,5-dimethoxy-4-ethylphenylethylamine (2C-E)
• 2,5-dimethoxy-4-propylphenethylamine (2C-P)
• 2,5-dimethoxy-4-iodophenethylamine (2C-I)
• 2,5-dimethoxy-4-fluorophenethylamine (2C-F)
• 2,5-dimethoxy-4-nitrophenethylamine (2C-N)
• 2,5-dimethoxy-4-ethylthiophenylethylamine (2C-T-2)
• 2,5-dimethoxy-4- ( iso ) -propylthiophenylethylamine (2C-T-4)
• 2,5-dimethoxy-4- ( n ) -propylthiophenylethylamine (2C-T-7)
• 2,5-dimethoxy-4-cyclopropylmethylthiophenylethylamine (2C-T-8)
• 2,5-dimethoxy-4-butylthiophenylethylamine (2C-T-9)
• 2,5-dimethoxy-4- (2-fluoroethylthio) phenylethylamine (2C-T-21)
• 2,5-dimethoxy-4-trifluoromethylphenethylamine (2C-TFM)

3,4-dimethoxyphenethylamine

• 3,4-dimethoxyphenethylamine

Trimethoxyphenylethylamine

• 3,4,5-trimethoxyphenylethylamine (mescaline, M)
• 2,3,4-trimethoxyphenylethylamine (IM)
• 2,4,5-trimethoxyphenylethylamine (TMPEA)

Amphetamines

_{(Trivial name for 1-phenyl-2-aminopropane)}

• amphetamine
• N -methylamphetamine (methamphetamine)
• Ephedrine , pseudoephedrine
• Norephedrine , norpseudoephedrine
• 4-hydroxyephedrine (oxilofrin)
• N -methylephedrine
• N -ethylamphetamine
• 4-methoxyamphetamine (PMA)
• 4- methoxy- N -methylamphetamine (PMMA, methyl-MA)
• Tiflorex
• Lisdexamfetamine (trade name "Elvanse")

Cathinones

• Cathinone (β-keto-amphetamine)
• N -methylcathinone (methcathinone, ephedron)
• 4-methylmethcathinone (4-MMC, mephedrone)
• 4-methylethcathinone (4-MEC)
• Pentedrone
• 3,4-methylenedioxycathinone (bk-MDA, MDC)
• 3,4-methylenedioxy- N -ethylcathinon (bk-MDEA, MDEC, Ethylon)
• 3,4-methylenedioxy- N -methylcathinone (bk-MDMA, MDMC, methylone)
• 3,4-methylenedioxypyrovalerone (MDPV)
• Pyrovalerone
• 3-chloro- N -tert-butylcathinone (bupropion)
• 2-diethylamino-1-phenylpropan-1-one (diethylpropion, amfepramon)

Dimethoxyamphetamine

• 3,4-dimethoxyamphetamine (3,4-DMA)
• 2,5-dimethoxyamphetamine (2,5-DMA)
• 2,5-dimethoxy-4-bromamphetamine (DOB)
• 2,5-dimethoxy-4-iodamphetamine (DOI)
• 2,5-dimethoxy-4-methylamphetamine (DOM, STP)
• 2,5-dimethoxy-4-nitroamphetamine (DON)
• 2,5-dimethoxy-4-chloramphetamine (DOC)
• 2,5-dimethoxy-4-fluoramphetamine (DOF)
• 2,5-dimethoxy-4-ethylamphetamine (DOET)
• 2,5-dimethoxy-4-propylamphetamine (DOPR)

Methylenedioxyamphetamine

• 3,4-methylenedioxyamphetamine (MDA)
• 3,4-methylenedioxy- N -methylamphetamine (MDMA)
• 3,4-methylenedioxy- N -ethylamphetamine (MDEA, MDE)
• 2-methoxy-3,4-methylenedioxyamphetamine (MMDA-3a)
• 3-methoxy-4,5-methylenedioxyamphetamine (MMDA)

Trimethoxy and trialkoxyamphetamines

• 3,4,5-trimethoxyamphetamine (TMA)
• 2,4,5-trimethoxyamphetamine (TMA-2)
• 2,3,4-trimethoxyamphetamine (TMA-3)
• 2,3,5-trimethoxyamphetamine (TMA-4)
• 2,3,6-trimethoxyamphetamine (TMA-5)
• 2,4,6-trimethoxyamphetamine (TMA-6)
• 3,5-dimethoxy-4-ethoxyamphetamine (3C-E)

1-phenyl-2-aminobutane

• 2- N -Methylamino-1- (3,4-methylenedioxyphenyl) butane (MBDB)
• 2-amino-1- (3,4-methylenedioxyphenyl) butane (BDB)

Overview

General structural formula of the phenylethylamines

Substituted phenethylamines , listed by structure

Surname	R N	R α	R β	R 2	R 3	R 4	R 5	R 6	chemical name
Tyramine	H	H	H	H	H	-OH	H	H	4-hydroxyphenethylamine
Dopamine	H	H	H	H	-OH	-OH	H	H	3,4-dihydroxyphenethylamine
adrenaline	-CH 3	H	-OH	H	-OH	-OH	H	H	β, 3,4-trihydroxy- N -methyl-phenethylamine
Norepinephrine	H	H	-OH	H	-OH	-OH	H	H	β, 3,4-trihydroxyphenethylamine
Synephrine	-CH 3	H	-OH	H	H	-OH	H	H	β, 4-dihydroxy- N -methyl-phenethylamine
Etilefrine	-CH 2 -CH 3	H	-OH	H	-OH	H	H	H	β, 3-dihydroxy- N -ethyl-phenethylamine
Norsynephrine	H	H	-OH	H	H	-OH	H	H	β, 4-dihydroxyphenethylamine
Phenylephrine	-CH 3	H	-OH	H	-OH	H	H	H	β, 3-dihydroxy- N -methyl-phenethylamine
Salbutamol	-C (CH 3 ) 3	H	-OH	H	-CH 2 OH	-OH	H	H	2- ( tert -butylamino) -1- (4-hydroxy-3-hydroxymethylphenyl) ethanol
Methylphenidate	–CH 2 –CH 2 –CH 2 –CH 2 -		-C (OCH 3 ) = O	H	H	H	H	H	N , α-butylene-β-methoxycarbonyl-phenethylamine
Ethyl phenidate	–CH 2 –CH 2 –CH 2 –CH 2 -		-C (OCH 2 -CH 3 ) = O	H	H	H	H	H	N , α-butylene-β-ethoxycarbonyl-phenethylamine
amphetamine	H	-CH 3	H	H	H	H	H	H	α-methyl-phenethylamine
4-fluoramphetamine	H	-CH 3	H	H	H	–F	H	H	4-fluoro-α-methyl-phenethylamine
4-chloramphetamine	H	-CH 3	H	H	H	-Cl	H	H	4-chloro-α-methyl-phenethylamine
4-bromamphetamine	H	-CH 3	H	H	H	–Br	H	H	4-bromo-α-methyl-phenethylamine
4-iodamphetamine	H	-CH 3	H	H	H	–I	H	H	4-iodo-α-methyl-phenethylamine
4-methoxyamphetamine	H	-CH 3	H	H	H	-OCH 3	H	H	4-methoxy-α-methyl-phenethylamine
4-methylthioamphetamine	H	-CH 3	H	H	H	–SCH 3	H	H	4-methylthio-α-methyl-phenethylamine
Methamphetamine	-CH 3	-CH 3	H	H	H	H	H	H	N -methyl amphetamine
4-fluoromethamphetamine	-CH 3	-CH 3	H	H	H	–F	H	H	4- fluoro- N -methyl-amphetamine
Ephedrine , pseudoephedrine	-CH 3	-CH 3	-OH	H	H	H	H	H	N -methyl-β-hydroxy-amphetamine
Oxilofrine	-CH 3	-CH 3	-OH	H	H	-OH	H	H	4-hydroxy ephedrine
Cathine	H	-CH 3	-OH	H	H	H	H	H	β-hydroxy amphetamine
Cathinone	H	-CH 3	= O	H	H	H	H	H	β-keto-amphetamine
Methcathinone	-CH 3	-CH 3	= O	H	H	H	H	H	N -methyl-β-keto-amphetamine
Bupropion	-C (CH 3 ) 3	-CH 3	= O	H	-Cl	H	H	H	3-chloro- N - tert -butyl-β-keto-amphetamine
Fenfluramine	-CH 2 CH 3	-CH 3	H	H	-CF 3	H	H	H	3-trifluoromethyl- N -ethyl-amphetamine
Phentermine	H	-CH 3 , -CH 3	H	H	H	H	H	H	α, α-dimethyl-phenethylamine
MDA	H	-CH 3	H	H	–O – CH 2 –O–		H	H	3,4- methylenedioxy- amphetamine
βk-MDA	H	-CH 3	= O	H	–O – CH 2 –O–		H	H	3,4-methylenedioxy-β-keto-amphetamine
MDMA	-CH 3	-CH 3	H	H	–O – CH 2 –O–		H	H	3,4-methylenedioxy- N -methyl-amphetamine
βk-MDMA	-CH 3	-CH 3	= O	H	–O – CH 2 –O–		H	H	3,4-methylenedioxy- N -methyl-β-keto-amphetamine
MDEA	-CH 2 CH 3	-CH 3	H	H	–O – CH 2 –O–		H	H	3,4-methylenedioxy- N -ethyl-amphetamine
βk-MDEA	-CH 2 CH 3	-CH 3	= O	H	–O – CH 2 –O–		H	H	3,4-methylenedioxy- N -ethyl-β-keto-amphetamine
5-APB	H	-CH 3	H	H	–CH = CH – O–		H	H	5- (2-aminopropyl) benzofuran
6-APB	H	-CH 3	H	H	–O – CH = CH–		H	H	6- (2-aminopropyl) benzofuran
Surname	R N	R α	R β	R 2	R 3	R 4	R 5	R 6	chemical name
Mescaline	H	H	H	H	-OCH 3	-OCH 3	-OCH 3	H	3,4,5-trimethoxyphenethylamine
TMA	H	-CH 3	H	H	-OCH 3	-OCH 3	-OCH 3	H	3,4,5-trimethoxy-amphetamine
TMA-2	H	-CH 3	H	-OCH 3	H	-OCH 3	-OCH 3	H	2,4,5-trimethoxy-amphetamine
TMA-3	H	-CH 3	H	-OCH 3	-OCH 3	-OCH 3	H	H	2,3,4-trimethoxy-amphetamine
TMA-4	H	-CH 3	H	-OCH 3	-OCH 3	H	-OCH 3	H	2,3,5-trimethoxy-amphetamine
TMA-5	H	-CH 3	H	-OCH 3	-OCH 3	H	H	-OCH 3	2,3,6-trimethoxy-amphetamine
TMA-6	H	-CH 3	H	-OCH 3	H	-OCH 3	H	-OCH 3	2,4,6-trimethoxy-amphetamine
DOM	H	-CH 3	H	-OCH 3	H	-CH 3	-OCH 3	H	2,5-dimethoxy-4-methyl-amphetamine
DOB	H	-CH 3	H	-OCH 3	H	–Br	-OCH 3	H	2,5-dimethoxy-4-bromo-amphetamine
DOI	H	-CH 3	H	-OCH 3	H	–I	-OCH 3	H	2,5-dimethoxy-4-iodo-amphetamine
DON	H	-CH 3	H	-OCH 3	H	-NO 2	-OCH 3	H	2,5-dimethoxy-4-nitro-amphetamine
DOC	H	-CH 3	H	-OCH 3	H	-Cl	-OCH 3	H	2,5-dimethoxy-4-chloro-amphetamine
2C-B	H	H	H	-OCH 3	H	–Br	-OCH 3	H	2,5-dimethoxy-4-bromophenethylamine
βk-2C-B	H	H	= O	-OCH 3	H	–Br	-OCH 3	H	2,5-dimethoxy-4-bromo-β-keto-phenethylamine
2C-C	H	H	H	-OCH 3	H	-Cl	-OCH 3	H	2,5-dimethoxy-4-chlorophenethylamine
2C-I	H	H	H	-OCH 3	H	–I	-OCH 3	H	2,5-dimethoxy-4-iodo-phenethylamine
2C-D	H	H	H	-OCH 3	H	-CH 3	-OCH 3	H	2,5-dimethoxy-4-methyl-phenethylamine
2C-E	H	H	H	-OCH 3	H	-CH 2 CH 3	-OCH 3	H	2,5-dimethoxy-4-ethyl-phenethylamine
2C-P	H	H	H	-OCH 3	H	-CH 2 CH 2 CH 3	-OCH 3	H	2,5-dimethoxy-4-propyl-phenethylamine
2C-F	H	H	H	-OCH 3	H	–F	-OCH 3	H	2,5-dimethoxy-4-fluoro-phenethylamine
2C-N	H	H	H	-OCH 3	H	-NO 2	-OCH 3	H	2,5-dimethoxy-4-nitro-phenethylamine
2C-T-2	H	H	H	-OCH 3	H	- SCH 2 CH 3	-OCH 3	H	2,5-dimethoxy-4-ethylthiophenethylamine
2C-T-4	H	H	H	-OCH 3	H	-S CHCH 3 CH 3	-OCH 3	H	2,5-dimethoxy-4- iso- propylthio-phenethylamine
2C-T-7	H	H	H	-OCH 3	H	-S CH 2 CH 2 CH 3	-OCH 3	H	2,5-dimethoxy-4-propylthio-phenethylamine
2C-T-8	H	H	H	-OCH 3	H	- SCH 2 CHCH 2 CH 2	-OCH 3	H	2,5-dimethoxy-4- cyclopropylmethylthio- phenethylamine
2C-T-9	H	H	H	-OCH 3	H	-S (CH 3 ) 3 C	-OCH 3	H	2,5-dimethoxy-4- tert - butylthio- phenethylamine
2C-T-21	H	H	H	-OCH 3	H	-SCH 2 CH 3 -F	-OCH 3	H	2,5-dimethoxy-4- (2-fluoroethylthio) phenethylamine
2C-TFM	H	H	H	-OCH 3	H	-CF 3	-OCH 3	H	2,5-dimethoxy-4-trifluoromethyl-phenethylamine
25I-NBOMe	-CH 2 -C 6 H 4 -OCH 3	H	H	-OCH 3	H	–I	-OCH 3	H	N - (2-methoxybenzyl) -2,5-dimethoxy-4-iodo-phenethylamine
25C-NBOMe	-CH 2 -C 6 H 4 -OCH 3	H	H	-OCH 3	H	-Cl	-OCH 3	H	N - (2-methoxybenzyl) -2,5-dimethoxy-4-chlorophenethylamine
25B-NBOMe	-CH 2 -C 6 H 4 -OCH 3	H	H	-OCH 3	H	–Br	-OCH 3	H	N - (2-methoxybenzyl) -2,5-dimethoxy-4-bromo-phenethylamine
25D-NBOMe	-CH 2 -C 6 H 4 -OCH 3	H	H	-OCH 3	H	-CH 3	-OCH 3	H	N - (2-methoxybenzyl) -2,5-dimethoxy-4-methyl-phenethylamine
25E-NBOMe	-CH 2 -C 6 H 4 -OCH 3	H	H	-OCH 3	H	-CH 2 CH 3	-OCH 3	H	N - (2-methoxybenzyl) -2,5-dimethoxy-4-ethyl-phenethylamine
25N-NBOMe	-CH 2 -C 6 H 4 -OCH 3	H	H	-OCH 3	H	-NO 2	-OCH 3	H	N - (2-methoxybenzyl) -2,5-dimethoxy-4-nitro-phenethylamine
25I-NBOH	-CH 2 -C 6 H 4 -OH	H	H	-OCH 3	H	–I	-OCH 3	H	N - (2-Hydroxybenzyl) -2,5-dimethoxy-4-iodo-phenethylamine
25C-NBOH	-CH 2 -C 6 H 4 -OH	H	H	-OCH 3	H	-Cl	-OCH 3	H	N - (2-Hydroxybenzyl) -2,5-dimethoxy-4-chloro-phenethylamine
25B-NBOH	-CH 2 -C 6 H 4 -OH	H	H	-OCH 3	H	–Br	-OCH 3	H	N - (2-Hydroxybenzyl) -2,5-dimethoxy-4-bromophenethylamine
Surname	R N	R α	R β	R 2	R 3	R 4	R 5	R 6	chemical name

Graphic overview

Overview of a small selection of endogenous, natural and synthetic phenylalkylamines, including some starting and degradation substances

See also

• Adrenoceptor , β-adrenoceptor
• α-blockers , β-blockers
• PIHKAL
• Tryptamine

literature

• D. Trachsel, D. Lehmann, Ch. Enzensperger: Phenethylamine From structure to function. Nightshade Science Edition, Solothurn, Switzerland, 2013, ISBN 978-3-03788-700-4 .
• Alexander Shulgin , Ann Shulgin: PIHKAL - A Chemical Love Story. Transform Press, Berkeley 1995, ISBN 0-9630096-0-5 .
• Stephen J. Chapman: Novel Psychoactive Spectra: NMR of (mostly) Novel Psychoactive Substances - BLOTTER. In: isomerdesign.com. June 25, 2018, accessed January 26, 2019 . 

Web links

• PIHKAL online - via erowid (English)
• Presentation methods (dissertation, pdf) (564 kB)