Phenylethylamines
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
- adrenaline
- Norepinephrine
- Dopamine (3,4-dihydroxy- β- phenylethylamine)
- Isoprenaline
- Orciprenaline
- Dobutamine
- Reproterol
- Terbutaline
- Dopexamine
- Metanephrine
Methoxyphenylethylamine
2,5-dimethoxyphenylethylamine
- 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
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
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
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)