Substituted phenethylamines

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Phenethylamine (R2=R3=R4=R5=RN=Rα=Rβ = H), the basis of all substituted phenethylamines.

The substituted phenethylamines are a family of chemical compounds that contain the 2-phenylethylamine chemical structure and also have additional modifications at the phenyl ring, sidechain, and/or amino group. Many of them are psychoactive drugs, including stimulants, psychedelics, and entactogens, which exert their effects primarily through modulation of the monoamine neurotransmitter systems. The substituted phenethylamines encompass the substituted amphetamines.

[edit] List of Substituted Phenethylamines

Selected Phenethylamines
Short Name RN Rα Rβ R2 R3 R4 R5 Full Name
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
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 N-ethylcathinone
Bupropion C(CH3)3 CH3 =O Cl 3-chloro-N-tert-butyl-β-ketoamphetamine
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
MDMA CH3 CH3 -O-CH2-O- 3,4-methylenedioxy-N-methylamphetamine
MDMC CH3 CH3 =O -O-CH2-O- 3,4-methylenedioxy-N-methyl-β-ketoamphetamine
DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methylamphetamine
DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromoamphetamine
DON CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitroamphetamine
2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromophenethylamine
2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chlorophenethylamine
DOI CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodoamphetamine
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

[edit] See also


v • d • e
Phenethylamines
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • DMPEA • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • α-Et-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Amphetamines
Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • Psi-DOM • TMA • TeMA
Stimulants: 4-MA • 4-MMA • 4-MTA • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • MMA • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Selegiline (Deprenyl) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: MDA • MDEA ("Eve") • MDHMA (FLEA) • MDMA ("Ecstasy", "Adam") • MDOH • MMDA • MMDMA
Phentermines
Stimulants: Chlorphentermine • Clortermine • Mephentermine • Phenpentermine • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Diethylcathinone (Diethylpropion, Amfepramone) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Butanamines
Entactogens: BDB (J) • BOH (Hydroxy-J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • MBDB (Methyl-J; "Eden")
Catecholamines
(and relatives..)
3-Iodotyrosine • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • Octopamine • Tyramine
Miscellaneous
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