Substituted amphetamine
Substituted amphetamines, or simply amphetamines, are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine, methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone, pyrovalerone, MDMA, and DOM.
Some of amphetamine's substituted derivatives occur in nature, for example in the leaves of Ephedra and khat plants. 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: stimulant, psychedelic, and entactogenic. 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 |
| Tranylcypromine | trans-2-Phenylcyclopropylamine | 0 |
| Methamphetamine | N-Methylamphetamine | 1 |
| Ethylamphetamine | N-Ethylamphetamine | 1 |
| Propylamphetamine | N-Propylamphetamine | 1 |
| Isopropylamphetamine | N-''iso-Propylamphetamine | 1 |
| Butylamphetamine | N''-n-Butylamphetamine | 1 |
| Pheniprazine | N-Aminoamphetamine | 1 |
| Phenatine | N-Nicotinoylamphetamine | 1 |
| Lisdexamfetamine | L-Lysine–amphetamine conjugate, - | 1 |
| Phentermine | α-Methylamphetamine | 1 |
| Phenylpropanolamine | β-Hydroxyamphetamine, - | 1 |
| Cathine | β-Hydroxyamphetamine, - | 1 |
| Cathinone | β-Ketoamphetamine | 1 |
| Ortetamine | 2-Methylamphetamine | 1 |
| 2-Fluoroamphetamine | 2-Fluoroamphetamine | 1 |
| 3-Methylamphetamine | 3-Methylamphetamine | 1 |
| 2-Phenyl-3-aminobutane | 2-Phenyl-3-aminobutane | 1 |
| 3-Fluoroamphetamine | 3-Fluoroamphetamine | 1 |
| Gepefrine | 3-Hydroxyamphetamine | 1 |
| Norfenfluramine | 3-Trifluoromethylamphetamine | 1 |
| 4-Methylamphetamine | 4-Methylamphetamine | 1 |
| para-Methoxyamphetamine | 4-Methoxyamphetamine | 1 |
| para-Ethoxyamphetamine | 4-Ethoxyamphetamine | 1 |
| 4-Methylthioamphetamine | 4-Methylthioamphetamine | 1 |
| Norpholedrine | 4-Hydroxyamphetamine | 1 |
| para-Bromoamphetamine | 4-Bromoamphetamine | 1 |
| para-Chloroamphetamine | 4-Chloroamphetamine | 1 |
| para-Fluoroamphetamine | 4-Fluoroamphetamine | 1 |
| para-Iodoamphetamine | 4-Iodoamphetamine | 1 |
| Mefenorex | N-amphetamine | 1 |
| Clobenzorex | N-amphetamine | 1 |
| Amfetaminil | N-Cyanobenzylamphetamine | 1 |
| Amfecloral | N-amphetamine | 1 |
| Racefemine | N-amphetamine | 1 |
| Dextrofemine | N-amphetamine, - | 1 |
| Fenproporex | N-2-Cyanoethylamphetamine | 1 |
| Prenylamine | N-amphetamine | 1 |
| Fenethylline | Theophylline–amphetamine conjugate | 1 |
| Dimethylamphetamine | N,''N-Dimethylamphetamine | 2 |
| Benzphetamine | N''-Benzyl-N-methylamphetamine | 2 |
| Deprenyl | N-Methyl-N-propargylamphetamine | 2 |
| D-Deprenyl | N-Methyl-N-propargylamphetamine, - | 2 |
| Selegiline | N-Methyl-N-propargylamphetamine, - | 2 |
| Metfendrazine | N-Amino-N-methylamphetamine | 2 |
| Mephentermine | N-Methyl-α-methylamphetamine | 2 |
| Phenpentermine | α,β-Dimethylamphetamine | 2 |
| Ephedrine | β-Hydroxy-N-methylamphetamine, - | 2 |
| Pseudoephedrine | β-Hydroxy-N-methylamphetamine, - | 2 |
| Metaraminol | 3,β-Dihydroxyamphetamine, - | 2 |
| Methcathinone | β-Keto-N-methylamphetamine | 2 |
| Ethcathinone | β-Keto-N-ethylamphetamine | 2 |
| Clortermine | 2-Chloro-α-methylamphetamine | 2 |
| Methoxymethylamphetamine | 3-Methoxy-4-methylamphetamine | 2 |
| Fenfluramine | 3-Trifluoromethyl-N-ethylamphetamine | 2 |
| Dexfenfluramine | 3-Trifluoromethyl-N-ethylamphetamine, - | 2 |
| 4-Methylmethamphetamine | 4-Methyl-N-methylamphetamine | 2 |
| para-Methoxymethamphetamine | 4-Methoxy-N-methylamphetamine | 2 |
| para-Methoxyethylamphetamine | 4-Methoxy-N-ethylamphetamine | 2 |
| Pholedrine | 4-Hydroxy-N-methylamphetamine | 2 |
| Chlorphentermine | 4-Chloro-α-methylamphetamine | 2 |
| para-Fluoromethamphetamine | 4-Fluoro-N-methylamphetamine | 2 |
| Xylopropamine | 3,4-Dimethylamphetamine | 2 |
| α-Methyldopamine | 3,4-Dihydroxyamphetamine | 2 |
| 3,4-Methylenedioxyamphetamine | 3,4-Methylenedioxyamphetamine | 2 |
| Dimethoxyamphetamine | X,X-Dimethoxyamphetamine | 2 |
| 6-APB | 6-benzofuran | 2 |
| Phenylpropylaminopentane | α-Desmethyl-α,N-dipropylamphetamine | 2 |
| Furfenorex | N--N-methylamphetamine | 2 |
| Fencamine | 8-Aminocaffeine–methamphetamine conjugate | 2 |
| Nordefrin | β,3,4-Trihydroxyamphetamine, - | 3 |
| Methylephedrine | β-Hydroxy-N-methylamphetamine, - | 3 |
| Etafedrine | β-Hydroxy-N-ethylamphetamine, - | 3 |
| Oxilofrine | β,4-Dihydroxy-N-methylamphetamine | 3 |
| Cinnamedrine | β-Hydroxy-N-methyl-N-cinnamylamphetamine | 3 |
| Methoxamine | 2,6-Dimethoxy-β-hydroxyamphetamine | 3 |
| Aleph | 2,5-Dimethoxy-4-methylthioamphetamine | 3 |
| Dimethoxybromoamphetamine | 2,5-Dimethoxy-4-bromoamphetamine | 3 |
| Dimethoxychloroamphetamine | 2,5-Dimethoxy-4-chloroamphetamine | 3 |
| Dimethoxyfluoroethylamphetamine | 2,5-Dimethoxy-4-fluoroethylamphetamine | 3 |
| Dimethoxyethylamphetamine | 2,5-Dimethoxy-4-ethylamphetamine | 3 |
| Dimethoxyfluoroamphetamine | 2,5-Dimethoxy-4-fluoroamphetamine | 3 |
| Dimethoxyiodoamphetamine | 2,5-Dimethoxy-4-iodoamphetamine | 3 |
| Dimethoxymethylamphetamine | 2,5-Dimethoxy-4-methylamphetamine | 3 |
| Dimethoxynitroamphetamine | 2,5-Dimethoxy-4-nitroamphetamine | 3 |
| Dimethoxypropylamphetamine | 2,5-Dimethoxy-4-propylamphetamine | 3 |
| Dimethoxytrifluoromethylamphetamine | 2,5-Dimethoxy-4-trifluoromethylamphetamine | 3 |
| Methylenedioxymethamphetamine | 3,4-Methylenedioxy-N-methylamphetamine | 3 |
| Methylenedioxyethylamphetamine | 3,4-Methylenedioxy-N-ethylamphetamine | 3 |
| Methylenedioxyhydroxyamphetamine | 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 | 3-Methoxy-4,5-methylenedioxyamphetamine | 3 |
| Trimethoxyamphetamine | 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 | β-Keto-4-methyl-N''-methylamphetamine | 3 |
| Methedrone | β-Keto-4-methoxy-N-methylamphetamine | 3 |
| Brephedrone | β-Keto-4-bromo-N-methylamphetamine | 3 |
| Flephedrone | β-Keto-4-fluoro-N-methylamphetamine | 3 |
| Ritodrine | 4,β-Dihydroxy-N-amphetamine | 3 |
| Buphenine | 4,β-Dihydroxy-N-'-amphetamine | 3 |
| Trecadrine | β-Hydroxy-N-methyl-N-'-amphetamine | 3 |
| Isoxsuprine | 4,β-Dihydroxy-N--amphetamine | 3 |
| Dioxifedrine | 3,4,β-Trihydroxy-N-methylamphetamine | 4 |
| Dioxethedrin | 3,4,β-Trihydroxy-N-ethylamphetamine | 4 |