A | B | C | D | E | F | G | H | CH | I | J | K | L | M | N | O | P | Q | R | S | T | U | V | W | X | Y | Z | 0 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9
| Substituted amphetamine | |
|---|---|
| Drug class | |
 Racemic amphetamine skeleton | |
| Class identifiers | |
| Chemical class | Substituted derivatives of amphetamine |
| Legal status | |
| In Wikidata | |
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|
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| L-amphetamine | D-amphetamine |
Substituted amphetamines are a class of compounds based upon the amphetamine structure;[1] it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents.[1][2][3][4] The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others.[2] Examples of substituted amphetamines are amphetamine (itself),[1][2] methamphetamine,[1] ephedrine,[1] cathinone,[1] phentermine,[1] mephentermine,[1] tranylcypromine,[5] bupropion,[1] methoxyphenamine,[1] selegiline,[1] amfepramone (diethylpropion),[1] pyrovalerone,[1] MDMA (ecstasy), and DOM (STP).
Some of amphetamine's substituted derivatives occur in nature, for example in the leaves of Ephedra and khat plants.[1] Amphetamine was first produced at the end of the 19th century. By the 1930s, amphetamine and some of its derivative compounds found use as decongestants in the symptomatic treatment of colds and also occasionally as psychoactive agents. Their effects on the central nervous system are diverse, but can be summarized by three overlapping types of activity: psychoanaleptic, hallucinogenic and empathogenic. Various substituted amphetamines may cause these actions either separately or in combination.
Partial list of substituted amphetamines
| Generic or Trivial Name | Chemical Name | # of Subs |
|---|---|---|
| Amphetamine | α-Methyl-phenethylamine | 0 |
| Methamphetamine | N-Methylamphetamine | 1 |
| Ethylamphetamine | N-Ethylamphetamine | 1 |
| Propylamphetamine | N-Propylamphetamine | 1 |
| Isopropylamphetamine | N-iso-Propylamphetamine | 1 |
| Phentermine | α-Methylamphetamine | 1 |
| Phenylpropanolamine (PPA) | β-Hydroxyamphetamine, (1R,2S)- | 1 |
| Cathine | β-Hydroxyamphetamine, (1S,2S)- | 1 |
| Cathinone | β-Ketoamphetamine | 1 |
| Ortetamine | 2-Methylamphetamine | 1 |
| 2-Fluoroamphetamine (2-FA) | 2-Fluoroamphetamine | 1 |
| 3-Methylamphetamine (3-MA) | 3-Methylamphetamine | 1 |
| 2-Phenyl-3-aminobutane | 2-Phenyl-3-aminobutane | 1 |
| Tranylcypromine | Trans-2-phenylcyclopropylamine | |
| 3-Fluoroamphetamine (3-FA) | 3-Fluoroamphetamine | 1 |
| Norfenfluramine | 3-Trifluoromethylamphetamine | 1 |
| 4-Methylamphetamine (4-MA) | 4-Methylamphetamine | 1 |
| para-Methoxyamphetamine (PMA) | 4-Methoxyamphetamine | 1 |
| para-Ethoxyamphetamine | 4-Ethoxyamphetamine | 1 |
| 4-Methylthioamphetamine (4-MTA) | 4-Methylthioamphetamine | 1 |
| Norpholedrine (α-Me-TRA) | 4-Hydroxyamphetamine | 1 |
| para-Bromoamphetamine (PBA, 4-BA) | 4-Bromoamphetamine | 1 |
| para-Chloroamphetamine (PCA, 4-CA) | 4-Chloroamphetamine | 1 |
| para-Fluoroamphetamine (PFA, 4-FA, 4-FMP) | 4-Fluoroamphetamine | 1 |
| para-Iodoamphetamine (PIA, 4-IA) | 4-Iodoamphetamine | 1 |
| Clobenzorex | N-(2-chlorobenzyl)-1-phenylpropan-2-amine | 1 |
| Dimethylamphetamine | N,N-Dimethylamphetamine | 2 |
| Benzphetamine | N-Benzyl-N-methylamphetamine | 2 |
| D-Deprenyl | N-Methyl-N-propargylamphetamine, (S)- | 2 |
| Selegiline | N-Methyl-N-propargylamphetamine, (R)- | 2 |
| Mephentermine | N-Methyl-α-methylamphetamine | 2 |
| Phenpentermine | α,β-Dimethylamphetamine | 2 |
| Ephedrine | β-Hydroxy-N-methylamphetamine, (1R,2S)- | 2 |
| Pseudoephedrine (PSE) | β-Hydroxy-N-methylamphetamine, (1S,2S)- | 2 |
| Methcathinone | β-Keto-N-methylamphetamine | 2 |
| Ethcathinone | β-Keto-N-ethylamphetamine | 2 |
| Clortermine | 2-Chloro-α-methylamphetamine | 2 |
| Methoxymethylamphetamine (MMA) | 3-Methoxy-4-methylamphetamine | 2 |
| Fenfluramine | 3-Trifluoromethyl-N-ethylamphetamine | 2 |
| Dexfenfluramine | 3-Trifluoromethyl-N-ethylamphetamine, (S)- | 2 |
| 4-Methylmethamphetamine (4-MMA) | 4-Methyl-N-methylamphetamine | 2 |
| para-Methoxymethamphetamine (PMMA) | 4-Methoxy-N-methylamphetamine | 2 |
| para-Methoxyethylamphetamine (PMEA) | 4-Methoxy-N-ethylamphetamine | 2 |
| Pholedrine | 4-Hydroxy-N-methylamphetamine | 2 |
| Chlorphentermine | 4-Chloro-α-methylamphetamine | 2 |
| para-Fluoromethamphetamine (PFMA, 4-FMA) | 4-Fluoro-N-methylamphetamine | 2 |
| Xylopropamine | 3,4-Dimethylamphetamine | 2 |
| α-Methyldopamine (α-Me-DA) | 3,4-Dihydroxyamphetamine | 2 |
| 3,4-Methylenedioxyamphetamine (MDA) | 3,4-Methylenedioxyamphetamine | 2 |
| Dimethoxyamphetamine (DMA) | X,X-Dimethoxyamphetamine | 2 |
| 6-APB | 6-(2-aminopropyl)benzofuran | 2 |
| Nordefrin (α-Me-NE) | β,3,4-Trihydroxyamphetamine, (R)- | 3 |
| Oxilofrine | β,4-Dihydroxy-N-methylamphetamine | 3 |
| Aleph | 2,5-dimethoxy-4-methylthioamphetamine | 3 |
| Dimethoxybromoamphetamine (DOB) | 2,5-Dimethoxy-4-bromoamphetamine | 3 |
| Dimethoxychloroamphetamine (DOC) | 2,5-Dimethoxy-4-chloroamphetamine | 3 |
| Dimethoxyfluoroethylamphetamine (DOEF) | 2,5-Dimethoxy-4-fluoroethylamphetamine | 3 |
| Dimethoxyethylamphetamine (DOET) | 2,5-Dimethoxy-4-ethylamphetamine | 3 |
| Dimethoxyfluoroamphetamine (DOF) | 2,5-Dimethoxy-4-fluoroamphetamine | 3 |
| Dimethoxyiodoamphetamine (DOI) | 2,5-Dimethoxy-4-iodoamphetamine | 3 |
| Dimethoxymethylamphetamine (DOM) | 2,5-Dimethoxy-4-methylamphetamine | 3 |
| Dimethoxynitroamphetamine (DON) | 2,5-Dimethoxy-4-nitroamphetamine | 3 |
| Dimethoxypropylamphetamine (DOPR) | 2,5-Dimethoxy-4-propylamphetamine | 3 |
| Dimethoxytrifluoromethylamphetamine (DOTFM) | 2,5-Dimethoxy-4-trifluoromethylamphetamine | 3 |
| Methylenedioxymethamphetamine (MDMA) | 3,4-Methylenedioxy-N-methylamphetamine | 3 |
| Methylenedioxyethylamphetamine (MDEA) | 3,4-Methylenedioxy-N-ethylamphetamine | 3 |
| Methylenedioxyhydroxyamphetamine (MDOH) | 3,4-Methylenedioxy-N-hydroxyamphetamine | 3 |
| 2-Methyl-MDA | 3,4-Methylenedioxy-2-methylamphetamine | 3 |
| 5-Methyl-MDA | 4,5-Methylenedioxy-3-methylamphetamine | 3 |
| Methoxymethylenedioxyamphetamine (MMDA) | 3-Methoxy-4,5-methylenedioxyamphetamine | 3 |
| Trimethoxyamphetamine (TMA) | X,X,X-Trimethoxyamphetamine | 3 |
| Dimethylcathinone | β-Keto-N,N-dimethylamphetamine | 3 |
| Diethylcathinone | β-Keto-N,N-diethylamphetamine | 3 |
| Bupropion | β-Keto-3-chloro-N-tert-butylamphetamine | 3 |
| Mephedrone (4-MMC) | β-Keto-4-methyl-N-methylamphetamine | 3 |
| Methedrone (PMMC) | β-Keto-4-methoxy-N-methylamphetamine | 3 |
| Brephedrone (4-BMC) | β-Keto-4-bromo-N-methylamphetamine | 3 |
| Flephedrone (4-FMC) | β-Keto-4-fluoro-N-methylamphetamine | 3 |
Prodrugs of amphetamine/methamphetamine
A variety of prodrugs of amphetamine and/or methamphetamine exist, and include amfecloral, amphetaminil, benzphetamine, clobenzorex, D-deprenyl, dimethylamphetamine, ethylamphetamine, fencamine, fenethylline, fenproporex, furfenorex, lisdexamfetamine, mefenorex, prenylamine, and selegiline.[6]
Structure
 | This section needs expansion with: substituents and structures for phenelzine, phenylephrine, phenylpropanolamine, selegiline, fenfluramine, mescaline, diethylpropion, desmethylselegiline, and benzphetamine from this table.[7]. You can help by adding to it. (February 2019) |
Amphetamines are a subgroup of the substituted phenethylamine class of compounds. Substitution of hydrogen atoms results in a large class of compounds. Typical reaction is substitution by methyl and sometimes ethyl groups at the amine and phenyl sites:[8][9][10]
| Substance | Substituents | Structure | Sources | ||||||
|---|---|---|---|---|---|---|---|---|---|
| N | α | β | phenyl group | ||||||
| 2 | 3 | 4 | 5 | ||||||
| Phenethylamine |  |
||||||||
| Amphetamine (α-methylphenylethylamine) | -CH3 | 
|
[7] | ||||||
| Methamphetamine (N-methylamphetamine) | -CH3 | -CH3 | 
|
[7] | |||||
| Phentermine (α-methylamphetamine) | -(CH3)2 | 
|
[7] | ||||||
| Ephedrine | -CH3 | -CH3 | -OH | -Ephedrin.svg){kind=small}
|
[7] | ||||
| Pseudoephedrine | -CH3 | -CH3 | -OH | -Pseudoephedrin.svg){kind=small}
|
[7] | ||||
| Cathinone | -CH3 | =O | 
|
[7] | |||||
| Methcathinone (ephedrone) | -CH3 | -CH3 | =O | 
|
[7] | ||||
| MDA (3,4-methylenedioxyamphetamine) | -CH3 | -O-CH2-O- | 
|
[7] | |||||
| MDMA (3,4-methylenedioxymethamphetamine) | -CH3 | -CH3 | -O-CH2-O- | .svg){kind=small}
|
[7] | ||||
| MDEA (3,4-methylenedioxy-N-ethylamphetamine) | -CH2-CH3 | -CH3 | -O-CH2-O- | 
|
[7] | ||||
| EDMA (3,4-ethylenedioxy-N-methylamphetamine) | -CH3 | -CH3 | -O-CH2-CH2-O- | 
|
|||||
| MBDB (N-methyl-1,3-benzodioxolylbutanamine) | -CH3 | -CH2-CH3 | -O-CH2-O- | 
|
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| PMA (para-methoxyamphetamine) | -CH3 | -O-CH3 | 
|
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| PMMA (para-methoxymethamphetamine) | -CH3 | -CH3 | -O-CH3 | 
|
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| 4-MTA (4-methylthioamphetamine) | -CH3 | -S-CH3 | 
|
||||||
| 3,4-DMA (3,4-dimethoxyamphetamine) | -CH3 | -O-CH3 | -O-CH3 | 
|
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| 3,4,5-Trimethoxyamphetamine (α-methylmescaline) |
Zdroj:https://en.wikipedia.org?pojem=Amphetamines Text je dostupný za podmienok Creative Commons Attribution/Share-Alike License 3.0 Unported; prípadne za ďalších podmienok. Podrobnejšie informácie nájdete na stránke Podmienky použitia.
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