Substituted amphetamine

A variety of prodrugs of amphetamine and/or methamphetamine exist, and include amfecloral, amfetaminil, benzphetamine, clobenzorex, D-deprenyl, deprenyl, dimethylamphetamine, ethylamphetamine, fencamine, fenethylline, fenproporex, furfenorex, lisdexamfetamine, mefenorex, prenylamine, and selegiline.[6] A number of synthetic Russian amphetamine derivatives have been developed, including alafen (amphetamine–β-alanine), feprosidnine, gamofen (amphetamine–GABA), mesocarb, methylphenatine, pabofen (amphetamine–PABA), phenatine (amphetamine–niacin; N-nicotinoylamphetamine), phenylphenamine (phenylamphetamine), propylphenamine (propylamphetamine), pyridoxiphen (amphetamine–pyridoxine), and thiophenatine (N-thionicotinoylamphetamine).Typical reaction is substitution by methyl and sometimes ethyl groups at the amine and phenyl sites:[8][9][10] Ephedra was used 5000 years ago in China as a medicinal plant; its active ingredients are alkaloids ephedrine, pseudoephedrine, norephedrine (phenylpropanolamine) and norpseudoephedrine (cathine).Over-the-counter use of substituted amphetamines was initiated in the early 1930s by the pharmaceutical company Smith, Kline & French (now part of GlaxoSmithKline), as a medicine (Benzedrine) for colds and nasal congestion.Subsequently, amphetamine was used in the treatment of narcolepsy, obesity, hay fever, orthostatic hypotension, epilepsy, Parkinson's disease, alcoholism and migraine.

This shows phenethylamine in blue with its substitution points marked. Amphetamine and its substituted derivatives contain a CH ₃ group at the alpha-position (R ^α ).

This shows amphetamine with its substitution points marked, excluding the N-position at the NH ₂ group which is unmarked. The wavy line between α carbon and CH ₃ group indicates isomerism; the CH ₃ group may either be towards or away from the viewer.

Amphetamine pills

AmphetamineAmphetamine (disambiguation)Drug classRacemic amphetamineSynonymsChemical classOptical isomersL-amphetamineD-amphetamineclass of compoundsderivativesubstitutinghydrogen atomssubstituentsstimulantsempathogenshallucinogensmethamphetamineephedrinecathinonephenterminemephenterminetranylcyprominebupropionmethoxyphenamineselegilineamfepramone (diethylpropion)pyrovaleronederivativesEphedracentral nervous systempsychoanaleptichallucinogenicempathogenicEthylamphetaminePropylamphetamineIsopropylamphetamineButylamphetaminePheniprazinePhenatineLisdexamfetaminePhenylpropanolamineCathineOrtetamine2-Fluoroamphetamine3-Methylamphetamine2-Phenyl-3-aminobutane3-FluoroamphetamineGepefrineNorfenfluramine4-Methylamphetaminepara-Methoxyamphetaminepara-Ethoxyamphetamine4-MethylthioamphetamineNorpholedrinepara-Bromoamphetaminepara-Chloroamphetaminepara-Fluoroamphetaminepara-IodoamphetamineMefenorexClobenzorexAmfetaminilAmfecloralRacefemineDextrofemineFenproporexPrenylamineFenethyllineDimethylamphetamineBenzphetamineDeprenylD-DeprenylMetfendrazinePhenpenterminePseudoephedrineMetaraminolMethcathinoneEthcathinoneClortermineMethoxymethylamphetamineFenfluramineDexfenfluramine4-Methylmethamphetaminepara-Methoxymethamphetaminepara-MethoxyethylamphetaminePholedrineChlorphenterminepara-FluoromethamphetamineXylopropamineα-Methyldopamine3,4-MethylenedioxyamphetamineDimethoxyamphetaminePhenylpropylaminopentaneFurfenorexFencamineNordefrinMethylephedrineEtafedrineOxilofrineCinnamedrineMethoxamineDimethoxybromoamphetamineDimethoxychloroamphetamineDimethoxyfluoroethylamphetamineDimethoxyethylamphetamineDimethoxyfluoroamphetamineDimethoxyiodoamphetamineDimethoxymethylamphetamineDimethoxynitroamphetamineDimethoxypropylamphetamineDimethoxytrifluoromethylamphetamineMethylenedioxyethylamphetamineMethylenedioxyhydroxyamphetamine2-Methyl-MDA5-Methyl-MDAMethoxymethylenedioxyamphetamineTrimethoxyamphetamineDimethylcathinoneDiethylcathinoneMephedroneMethedroneBrephedroneFlephedroneRitodrineBuphenineTrecadrineIsoxsuprineDioxifedrineDioxethedrinprodrugsList of Russian drugssyntheticRussianfeprosidninemesocarbpyridoxiphenphenelzinephenylephrinemescalinediethylpropiondesmethylselegilinephenethylamineCH3 groupNH2 groupsubstituted phenethylaminemethylethyl groupsphenylphenyl group3,4-DMA3,4,5-TrimethoxyamphetamineHistory and culture of substituted amphetaminesmedicinal plantalkaloidsnorephedrinenorpseudoephedrineEthiopiaRomanianLazăr EdeleanudextroamphetamineasthmaGlaxoSmithKlineBenzedrinenasal congestionnarcolepsyobesityhay feverorthostatic hypotensionepilepsyParkinson's diseasealcoholismmigraineWorld War IIdepressionUnited StatesAlexander ShulginDrug Enforcement AdministrationentactogenicAustraliaracemicLevoamphetamine3,4,5-TMASubstituted phenethylaminesSubstituted β-hydroxyamphetaminesSubstituted methylenedioxyphenethylaminesSubstituted cathinonesSubstituted phenylmorpholinesSubstituted tryptaminesSubstituted α-alkyltryptaminesPiHKALThe Shulgin IndexWayback Machineisopropylamineside chaincyclizedcyclopropylAdderallBiomolecular targets5-HT1A receptor