Phenylethylamine
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- Phenylethylamin
- Stoffgruppe
Als Phenylethylamine (auch Phenylalkylamine oder β-Phenylalkylamine) bezeichnet man eine Gruppe chemischer Verbindungen, die sich vom Phenylethylamin ableiten. Zahlreiche Phenylethylamine besitzen eine weite Verbreitung in der Natur (z. B. Tyramin und Dopamin), während andere künstlichen Ursprungs sind (z. B. Amphetamine).
Natürlich vorkommende Phenylethylamine besitzen beispielsweise als L-Aminosäuren (L-Tyrosin und L-Phenylalanin) eine grundlegende Bedeutung für das Leben. Im menschlichen und tierischen Organismus spielen Phenylethylamine darüber hinaus eine wichtige Rolle als Neurotransmitter (z. B. Dopamin) und Hormone (z. B. Adrenalin). Viele im Pflanzenreich vorkommende Alkaloide sind ebenfalls den Phenylethylamine zuzuordnen (z. B. Ephedrin, Mescalin).
Synthetisch hergestellte Phenylethylamine, wie z. B. Verapamil oder Etilefrin, finden als Arzneimittel Anwendung. Zahlreiche Verbindungen dieser Stoffgruppe besitzen psychotrope Eigenschaften.
Phenylethylamine
- Phenethylamin (PEA)
- 4-Hydroxyphenylethylamin (Tyramin)
- 1-(3-Hydroxyphenyl)-2-(ethylamino)ethanol (Etilefrin)
- 1-(4-Hydroxyphenyl)-2-(methylamino)ethanol (Synephrin)
- 4-(2-Amino-1-hydroxy-ethyl)phenol (Norsynephrin)
Katecholamine
- Adrenalin
- Noradrenalin
- Dopamin (3,4-Dihydroxy-β-phenylethylamin)
- Isoprenalin
- Orciprenalin
- Dobutamin
- Reproterol
- Terbutalin
Methoxyphenylethylamine
Dimethoxyphenylethylamine
- 2,5-Dimethoxy-4-bromphenethylamin (2C-B)
- 2,5-Dimethoxy-4-chlorphenethylamin (2C-C)
- 2,5-Dimethoxy-4-methylphenylethylamin (2C-D)
- 2,5-Dimethoxy-4-ethylphenylethylamin (2C-E)
- 2,5-Dimethoxy-4-propylphenethylamin (2C-P)
- 2,5-Dimethoxy-4-iodphenethylamin (2C-I)
- 2,5-Dimethoxy-4-fluorphenethylamin (2C-F)
- 2,5-Dimethoxy-4-nitrophenethylamin (2C-N)
- 2,5-Dimethoxy-4-ethylthiophenylethylamin (2C-T-2)
- 2,5-Dimethoxy-4-(iso)-propylthiophenylethylamin (2C-T-4)
- 2,5-Dimethoxy-4-(n)-propylthiophenylethylamin (2C-T-7)
- 2,5-Dimethoxy-4-cyclopropylmethylthiophenylethylamin (2C-T-8)
- 2,5-Dimethoxy-4-butylthiophenylethylamin (2C-T-9)
- 2,5-Dimethoxy-4-(2-fluorethylthio)phenylethylamin (2C-T-21)
Trimethoxyphenylethylamine
- 3,4,5-Trimethoxyphenylethylamin (Meskalin, M)
- 2,3,4-Trimethoxyphenylethylamin (IM)
- 2,4,5-Trimethoxyphenylethylamin (TMPEA)
Amphetamine
(Trivialbezeichnung für 1-Phenyl-2-aminopropane)
- Ephedrin, Pseudoephedrin
- Norephedrin / Cathin
- 4-Hydroxyephedrin (Oxilofrin)
- N-Methylephedrin
- Amphetamin
- Cathinon (β-Keto-amphetamin)
- N-Methylamphetamin
- N-Ethylamphetamin
- 4-Methoxyamphetamin (PMA)
- 4-Methoxy-N-methylamphetamin (PMMA, Methyl-MA)
- 4-Methylmeth-β-keto-amphetamin (4-MMC, Mephedron)
- Tiflorex
Dimethoxyamphetamine
- 3,4-Dimethoxyamphetamin (3,4-DMA)
- 2,5-Dimethoxyamphetamin (2,5-DMA)
- 2,5-Dimethoxy-4-bromamphetamin (DOB)
- 2,5-Dimethoxy-4-iodamphetamin (DOI)
- 2,5-Dimethoxy-4-methylamphetamin (DOM, STP)
- 2,5-Dimethoxy-4-nitroamphetamin (DON)
- 2,5-Dimethoxy-4-chloramphetamin (DOC)
- 2,5-Dimethoxy-4-fluoramphetamin (DOF)
- 2,5-Dimethoxy-4-ethylamphetamin (DOET)
- 2,5-Dimethoxy-4-propylamphetamin (DOPR)
Methylendioxyamphetamine
- 3,4-Methylendioxyamphetamin (MDA)
- 3,4-Methylendioxy-β-keto-amphetamin (bk-MDA, MDC)
- 3,4-Methylendioxy-N-methylamphetamin (MDMA)
- 3,4-Methylendioxy-N-methyl-β-keto-amphetamin (bk-MDMA, MDMC, Methylon)
- 3,4-Methylendioxy-N-ethylamphetamin (MDEA, MDE)
- 3,4-Methylendioxy-N-ethyl-β-keto-amphetamin (bk-MDEA, MDEC, Ethylon)
- 2-Methoxy-3,4-methylendioxyamphetamin (MMDA-3a)
- 3-Methoxy-4,5-methylendioxyamphetamin (MMDA)
Trimethoxy- und Trialkoxyamphetamine
- 3,4,5-Trimethoxyamphetamin (TMA)
- 3,5-Dimethoxy-4-ethoxyamphetamin (3C-E)
- 2,4,5-Trimethoxyamphetamin (TMA-2)
- 2,3,4-Trimethoxyamphetamin (TMA-3)
- 2,3,5-Trimethoxyamphetamin (TMA-4)
- 2,3,6-Trimethoxyamphetamin (TMA-5)
- 2,4,6-Trimethoxyamphetamin (TMA-6)
1-Phenyl-2-aminobutane
- 2-N-Methylamino-1-(3,4-methylendioxyphenyl)butan (MBDB)
- 2-Amino-1-(3,4-methylendioxyphenyl)butan (BDB)
Übersicht
| Name | RN | Rα | Rβ | R2 | R3 | R4 | R5 | chemischer Name |
|---|---|---|---|---|---|---|---|---|
| Tyramin | –OH | 4-Hydroxy-phenethylamin | ||||||
| Dopamin | –OH | –OH | 3,4-Dihydroxy-phenethylamin | |||||
| Adrenalin | –CH3 | –OH | –OH | –OH | β,3,4-Trihydroxy-N-methyl-phenethylamin | |||
| Noradrenalin | –OH | –OH | –OH | β,3,4-Trihydroxy-phenethylamin | ||||
| Synephrin | –CH3 | –OH | –OH | β,4-Dihydroxy-N-methyl-phenethylamin | ||||
| Etilefrin | –CH2–CH3 | –OH | –OH | β,3-Dihydroxy-N-ethyl-phenethylamin | ||||
| Norsynephrin | –OH | –OH | β,4-Dihydroxy-phenethylamin | |||||
| Phenylephrin | –CH3 | –OH | –OH | β,3-Dihydroxy-N-methyl-phenethylamin | ||||
| Salbutamol | –C(CH3)3 | –OH | –CH2OH | –OH | 2-(tert-Butylamino)-1-(4-hydroxy-3-hydroxymethylphenyl)ethanol | |||
| Methylphenidat | –CH2–CH2–CH2–CH2– | –C(OCH3)=O | N,α-butylen-β-methoxycarbonyl-phenethylamin | |||||
| Ethylphenidat | –CH2–CH2–CH2–CH2– | –C(OCH2–CH3)=O | N,α-butylen-β-ethoxycarbonyl-phenethylamin | |||||
| Amphetamin | –CH3 | α-Methyl-phenethylamin | ||||||
| 4-Fluoramphetamin | –CH3 | –F | 4-Fluor-α-methyl-phenethylamin | |||||
| 4-Chloramphetamin | –CH3 | –Cl | 4-Chlor-α-methyl-phenethylamin | |||||
| 4-Bromamphetamin | –CH3 | –Br | 4-Brom-α-methyl-phenethylamin | |||||
| 4-Iodamphetamin | –CH3 | –I | 4-Iod-α-methyl-phenethylamin | |||||
| 4-Methoxyamphetamin | –CH3 | –OCH3 | 4-Methoxy-α-methyl-phenethylamin | |||||
| 4-Methylthioamphetamin | –CH3 | –SCH3 | 4-Methylthio-α-methyl-phenethylamin | |||||
| Methamphetamin | –CH3 | –CH3 | N-Methyl-amphetamin | |||||
| 4-Fluormethamphetamin | –CH3 | –CH3 | –F | 4-Fluor-N-methyl-amphetamin | ||||
| Ephedrin, Pseudoephedrin |
–CH3 | –CH3 | –OH | N-Methyl-β-hydroxy-amphetamin | ||||
| Oxilofrin | –CH3 | –CH3 | –OH | –OH | 4-Hydroxy-ephedrin | |||
| Cathin | –CH3 | –OH | β-Hydroxy-amphetamin | |||||
| Cathinon | –CH3 | =O | β-Keto-amphetamin | |||||
| Methcathinon | –CH3 | –CH3 | =O | N-Methyl-β-keto-amphetamin | ||||
| Bupropion | –C(CH3)3 | –CH3 | =O | –Cl | 3-Chlor-N-tert-butyl-β-keto-amphetamin | |||
| Fenfluramin | –CH2CH3 | –CH3 | –CF3 | 3-Trifluormethyl-N-ethyl-amphetamin | ||||
| Phentermin | –CH3,–CH3 | α,α-Dimethyl-phenethylamin | ||||||
| Mescalin | –OCH3 | –OCH3 | –OCH3 | 3,4,5-Trimethoxy-phenethylamin | ||||
| TMA | –CH3 | –OCH3 | –OCH3 | –OCH3 | 3,4,5-Trimethoxy-amphetamin | |||
| MDA | –CH3 | –O–CH2–O– | 3,4-Methylendioxy-amphetamin | |||||
| bk-MDA | –CH3 | =O | –O–CH2–O– | 3,4-Methylendioxy-β-keto-amphetamin | ||||
| MDMA | –CH3 | –CH3 | –O–CH2–O– | 3,4-Methylendioxy-N-methyl-amphetamin | ||||
| bk-MDMA | –CH3 | –CH3 | =O | –O–CH2–O– | 3,4-Methylendioxy-N-methyl-β-keto-amphetamin | |||
| MDEA | –CH2CH3 | –CH3 | –O–CH2–O– | 3,4-Methylendioxy-N-ethyl-amphetamin | ||||
| bk-MDEA | –CH2CH3 | –CH3 | =O | –O–CH2–O– | 3,4-Methylendioxy-N-ethyl-β-keto-amphetamin | |||
| DOM | –CH3 | –OCH3 | –CH3 | –OCH3 | 2,5-Dimethoxy-4-methyl-amphetamin | |||
| DOB | –CH3 | –OCH3 | –Br | –OCH3 | 2,5-Dimethoxy-4-brom-amphetamin | |||
| DOI | –CH3 | –OCH3 | –I | –OCH3 | 2,5-Dimethoxy-4-iod-amphetamin | |||
| DON | –CH3 | –OCH3 | –NO2 | –OCH3 | 2,5-Dimethoxy-4-nitro-amphetamin | |||
| DOC | –CH3 | –OCH3 | –Cl | –OCH3 | 2,5-Dimethoxy-4-chlor-amphetamin | |||
| 2C-B | –OCH3 | –Br | –OCH3 | 2,5-Dimethoxy-4-brom-phenethylamin | ||||
| 2C-C | –OCH3 | –Cl | –OCH3 | 2,5-Dimethoxy-4-chlor-phenethylamin | ||||
| 2C-I | –OCH3 | –I | –OCH3 | 2,5-Dimethoxy-4-iod-phenethylamin | ||||
| 2C-D | –OCH3 | –CH3 | –OCH3 | 2,5-Dimethoxy-4-methyl-phenethylamin | ||||
| 2C-E | –OCH3 | –CH2CH3 | –OCH3 | 2,5-Dimethoxy-4-ethyl-phenethylamin | ||||
| 2C-P | –OCH3 | –CH2CH3CH3 | –OCH3 | 2,5-Dimethoxy-4-propyl-phenethylamin | ||||
| 2C-F | –OCH3 | –F | –OCH3 | 2,5-Dimethoxy-4-fluor-phenethylamin | ||||
| 2C-N | –OCH3 | –NO2 | –OCH3 | 2,5-Dimethoxy-4-nitro-phenethylamin | ||||
| 2C-T-2 | –OCH3 | –SCH2CH3 | –OCH3 | 2,5-Dimethoxy-4-ethylthio-phenethylamin | ||||
| 2C-T-4 | –OCH3 | –SCHCH3CH3 | –OCH3 | 2,5-Dimethoxy-4-iso-propylthio-phenethylamin | ||||
| 2C-T-7 | –OCH3 | –SCH2CH2CH3 | –OCH3 | 2,5-Dimethoxy-4-propylthio-phenethylamin | ||||
| 2C-T-8 | –OCH3 | –SCH2CHCH2CH2 | –OCH3 | 2,5-Dimethoxy-4-cyclopropylmethylthio-phenethylamin | ||||
| 2C-T-9 | –OCH3 | –S(CH3)3C | –OCH3 | 2,5-Dimethoxy-4-tert-butylthio-phenethylamin | ||||
| 2C-T-21 | –OCH3 | –SCH2CH3–F | –OCH3 | 2,5-Dimethoxy-4-(2-fluorethylthio)-phenethylamin | ||||
| 25I-NBOMe | –CH2–C6H4–OCH3 | –OCH3 | –I | –OCH3 | 2-(4-Iod-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamin | |||
| 25C-NBOMe | –CH2–C6H4–OCH3 | –OCH3 | –Cl | –OCH3 | 2-(4-Chlor-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamin | |||
| 25B-NBOMe | –CH2–C6H4–OCH3 | –OCH3 | –Br | –OCH3 | 2-(4-Brom-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamin | |||
| 5-APB | –CH3 | –CH=CH–O– | 5-(2-Aminopropyl)benzofuran | |||||
| 6-APB | –CH3 | –O–CH=CH– | 6-(2-Aminopropyl)benzofuran | |||||
| Name | RN | Rα | Rβ | R2 | R3 | R4 | R5 | chemischer Name |
Grafische Übersicht
Übersicht über eine kleine Auswahl an endogenen, natürlichen und synthetischen Phenylalkylaminen, inklusive einiger Ausgangs- und Abbaustoffe
Siehe auch
- Adrenozeptor, β-Adrenozeptor
- α-Blocker, β-Blocker
- PIHKAL
- Tryptamin
Weblinks
- PIHKAL online – via erowid (englisch)
- Darstellungsmethoden (Dissertation, pdf) (564 kB)