3,4-Dichloroamphetamine
3,4-Dichloroamphetamine (3,4-DCA), is an amphetamine derived drug invented by Eli Lilly in the 1960s, which has a number of pharmacological actions.It acts as a highly potent and selective serotonin releasing agent (SSRA) and binds to the serotonin transporter with high affinity,[1][2][3][4] but also acts as a selective serotonergic neurotoxin in a similar manner to the related para-chloroamphetamine (PCA), though with slightly lower potency.[5] It is also a monoamine oxidase inhibitor (MAOI),[6] as well as a very potent inhibitor of the enzyme phenylethanolamine N-methyl transferase which normally functions to transform noradrenaline into adrenaline in the body.Reaction with sodium methoxide and ethyl acetate gives α-acetoxy-3,4-dichlorophenylacetonitrile, (3).Removal of the nitrile group in the presence of sulfuric acid gives 3,4-dichlorophenylacetone (4).
ATC codeIUPAC nameCAS NumberChemSpiderChEMBLCompTox DashboardECHA InfoCardFormulaMolar massSMILESamphetamineEli Lillypotentselectiveserotonin releasing agentserotonin transporteraffinityserotonergic neurotoxinpara-chloroamphetaminemonoamine oxidase inhibitorinhibitorphenylethanolamine N-methyl transferasenoradrenalineadrenalineethyl acetate2,4-Dichloroamphetamine3-Chloroamphetamine3-Methoxy-4-methylamphetamineCericlamineChlorphentermineClortermineEtolorex3,4-Methylenedioxyamphetaminepara-MethoxyamphetamineMonoaminergic neurotoxinsDopaminergic2′-CH3-MPTP (2′-methyl-MPTP)2,4,5-THA2,4,5-THMA5,6-DHT6-HydroxydopaALDH inhibitorsdisulfirammethylmercuryBenomylDaidzinDieldrinDopamineFenpropathrinHaloperidolMancozebMephedroneMethamphetamineMethcathinoneMethyloneMPP+ (cyperquat)NorsalsolinolOxidopamine (6-OHDA)ParaquatRotenoneSalsolinolNoradrenergic2′-NH2-MPTP (2′-amino-MPTP)5,7-DHTDOPEGALMDA (tenamfetamine)XylamineSerotonergic2,4-DCA4-CAB (α-ethyl-PCA)5-MAPBFenfluramineHHA (α-methyldopamine)HHMA (α-methylepinine, α,N-dimethyldopamine)MDMA (midomafetamine)Norfenfluramine5-HIALMonoamine releasing agentsFenbutrazateFenmetramideMorazoneMorforexPhendimetrazinePhenmetrazinePseudophenmetrazineAminorexClominorexCyclazodoneFenozoloneFluminorexPemolineThozalinone2-OH-PEAAlfetamineAmfecloralAmfepentorexAmfepramoneDextroamphetamineLevoamphetamineAmphetaminilβ-Me-PEABenzphetamineBuphedroneButyloneCathineCathinoneClobenzorexD-DeprenylDimethylamphetamineEphedrineEthcathinoneEthyloneEtilamfetamineFamprofazoneFenethyllineFenproporexFlephedroneFludorexFurfenorexHordenine4-HydroxyamphetamineIofetamine (123I)LisdexamfetamineLophophineMefenorexMetamfepramone