Phenylisobutylamine

Phenylisobutylamine, also known as α-ethylphenethylamine (AEPEA) or as butanphenamine (B), is a stimulant drug of the phenethylamine and amphetamine families.Phenylisobutylamine acts as a norepinephrine–dopamine releasing agent (NDRA) and has been found to produce stimulant-like and reinforcing effects in animals.[1][2][3] It shows much lower potency and a greater preference for induction of norepinephrine release compared to dextroamphetamine.[4][5][6][7] The phenylisobutylamine counterparts of psychedelic phenethylamines and amphetamines, for instance MBDB (the α-ethyl homologue of MDMA) and Ariadne (the α-ethyl homologue of DOM), show greatly reduced or abolished psychedelic effects in comparison.[10][4] In the case of Ariadne specifically, it may be due to reduced efficacy in activating the serotonin 5-HT2A receptor.
Routes ofadministrationDrug classNorepinephrine–dopamine releasing agentStimulantATC codeLegal statusSchedule II (isomer of Methamphetamine)IUPAC nameCAS NumberChemSpiderCompTox DashboardFormulaMolar massSMILESphenethylamineamphetaminehomologuemethylalpha positionside chainreinforcingpotencyinduction of norepinephrine releasedextroamphetamineisobutylaminederivativesN,α-Diethylphenethylamine5-MBPB6-MBPBBuphedroneN-Ethylbuphedrone3F-NEB4-MethylbuphedroneButyloneEutyloneDibutyloneAriadne4C-T-2α-Pyrrolidinobutiophenonechainspentedronepentylonehexedronemexedroneserotonin–norepinephrine–dopamine releasing agentselectiveserotonin–norepinephrine releasing agentnorepinephrineα-ethyltryptamineα-methyltryptamineefficacyserotonin5-HT2A receptorα-PropylphenethylamineStimulantsAdamantanesAdapromineAmantadineBromantaneMemantineRimantadineAdenosine antagonists8-Chlorotheophylline8-Cyclopentyltheophylline8-PhenyltheophyllineAminophyllineCaffeineCGS-15943DimethazanIstradefyllineParaxanthineSCH-58261TheobromineTheophyllineAlkylaminesCyclopentamineCypenamineCyprodenateHeptaminolIsomethepteneMethylhexaneamineOctodrinePropylhexedrineTuaminoheptaneAmpakinesCX-516CX-546CX-614CX-691CX-717IDRA-21LY-404,187LY-503,430NooglutylOrg 26576S-18986SunifiramUnifiramArylcyclohexylaminesBenocyclidineDieticyclidineEsketamineEticyclidineGacyclidineKetaminePhencyclaminePhencyclidineRolicyclidineTenocyclidineTiletamineBenzazepines6-Br-APBSKF-77434SKF-81297SKF-82958Cathinones3,4-DMMC4-Methylcathinone4-MEAP4-MethylpentedroneAmfepramoneBenzedroneBupropionCathinoneDimethylcathinoneEthcathinoneEthyloneFlephedroneIsoethcathinoneMephedroneMethcathinoneMethedroneMethylenedioxycathinoneMethyloneN-EthylhexedronePhthalimidopropiophenoneCholinergicsA-84,543A-366,833ABT-202ABT-418AR-R17779AltiniclineAnabasineArecolineBradaniclineCotinineCytisineDianiclineEpibatidineEpiboxidineGTS-21IsproniclineNicotinePHA-543,613PNU-120,596PNU-282,987PozaniclineRivaniclineSazetidine ASIB-1553ASSR-180,711TC-1698TC-1827TC-2216TebaniclineUB-165VareniclineWAY-317,538ConvulsantsAnatoxin-aBicucullineFlurothylGabazinePentetrazolPicrotoxinStrychnineThujoneEugeroicsAdrafinilArmodafinilCRL-40,940CRL-40,941FluorenolModafinilOxazolines4-MethylaminorexAminorexClominorexCyclazodoneFenozoloneFluminorexPemolineThozalinonePhenethylamines1-(4-Methylphenyl)-2-aminobutane1-Methylamino-1-(3,4-methylenedioxyphenyl)propane2-Fluoroamphetamine2-Fluoromethamphetamine2-OH-PEA2-Phenyl-3-aminobutane2,3-MDA3-Fluoroamphetamine3-Fluoroethamphetamine3-Methoxyamphetamine3-Methylamphetamine4-Fluoroamphetamine4-FluoromethamphetamineAL-1095Alfetaminea-EthylphenethylamineAmfecloralAmfepentorexAmidephrine2-Amino-1,2-dihydronaphthalene2-Aminoindane5-(2-Aminopropyl)indole2-AminotetralinAcridorexLevoamphetamineAmphetaminilArbutamineβ-Methylphenethylamineβ-PhenylmethamphetamineBenfluorexBenzphetamine3-BenzhydrylmorpholineCamfetamineCathineChlorphentermineCilobamineCinnamedrineClenbuterolClobenzorexCloforexClortermineD-DeprenylDenopamineDimethoxyamphetamineDimethylamphetamineDobutamineDextrodopaLevodopaDopamineDopexamineDroxidopaEphedrineEpinephrineEpinineEtafedrineEthylnorepinephrineEtilamfetamineEtilefrineFamprofazoneFencamfaminFencamineFenethyllineFenfluramineDexfenfluramineLevofenfluramineFenproporexFeprosidnineFludorexFormetorexFurfenorexGepefrineHexapradolHordenine4-Hydroxyamphetamine5-Iodo-2-aminoindaneIbopamineIndanylamphetamineIofetamineIsoetarineIsoprenalineL-DeprenylLefetamineLisdexamfetamineLophophineMDA (tenamfetamine)MDMA (midomafetamine)MDMPEAMefenorexMephentermineMetanephrineMetaraminolMesocarbMethamphetamineDextromethamphetamineLevomethamphetamineMethoxamineMethoxyphenamineMorforexN,alpha-DiethylphenylethylamineN,N-DimethylphenethylamineNaphthylamphetamineNisoxetineNorfenefrineNorfenfluramineNormetanephrineL-NorpseudoephedrineOctopamineOrciprenalineOrtetamineOxifentorexOxilofrinePentorexPhenatinePhenpromethaminePhenterminePhenylalaninePhenylephrinePhenylpropanolaminePholedrinePrenylaminePropylamphetaminePseudoephedrineRopiniroleSalbutamolLevosalbutamolSibutramineSolriamfetolSynephrineTheodrenalineTiflorexTranylcypromineTyramineTyrosineXylopropamineZylofuraminePhenylmorpholines3-FluorophenmetrazineFenbutrazateFenmetramideManifaxineMorazoneOxaflozanePD-128,907PhendimetrazinePhenmetrazine2-Phenyl-3,6-dimethylmorpholinePseudophenmetrazineRadafaxinePiperazines2C-B-BZP3C-PEPDBL-583GBR-12783GBR-12935GBR-13069GBR-13098GBR-13119JJC8-088VanoxerinePiperidines1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine2-Benzylpiperidine2-Methyl-3-phenylpiperidine3,4-Dichloromethylphenidate4-Benzylpiperidine4-Fluoromethylphenidate4-MethylmethylphenidateDesoxypipradrolDifemetorexDiphenylpyralineEthylnaphthidateEthylphenidateMethylnaphthidateIsopropylphenidateJZ-IV-10MethylphenidateDexmethylphenidateNocainePhacetoperanePipradrolPropylphenidateSerdexmethylphenidateSCH-5472Pyrrolidines2-Diphenylmethylpyrrolidine4-Cl-PVP5-DBFPVα-PPPα-PBPα-PCYPα-PHiPα-PHPα-PHPPα-PVPα-PVTDiphenylprolinolIndapyrophenidoneNaphyronePicilorexProlintanePyrovaleroneRacetamsOxiracetamPhenylpiracetamPhenylpiracetam hydrazideTropanes4-fluorotropacocaine4'-FluorococaineAltropane (IACFT)BrasofensineCFT (WIN 35,428)β-CIT (RTI-55)CocaethyleneCocaineDichloropane (RTI-111)DifluoropineFE-β-CPPITFP-β-CPPITIoflupane (123I)NorcocaineRTI-31RTI-32RTI-51RTI-112RTI-113RTI-120RTI-121 (IPCIT)RTI-126RTI-150RTI-177RTI-229RTI-336RTI-354RTI-371RTI-386SalicylmethylecgonineTesofensineTroparil (β-CPT, WIN 35,065-2)TropoxaneTryptamines4-HO-αMT4-Methyl-αET4-Methyl-αMT5-Chloro-αMT5-Fluoro-αMT5-MeO-αET5-MeO-αMT5-MeO-DIPT6-Fluoro-αMT7-Methyl-αET3,3-DiphenylcyclobutanamineAmfonelic acidAmineptineAmiphenazoleAtipamezoleAtomoxetineBemegrideBenzydamineBTS 74,398CentanafadineCiclazindolClofenciclanCropropamideCrotetamideDesipramineDiclofensineDimethocaineEfaroxanEtamivanFenisorexFenpentadiolGamfexineGilutensinGSK1360707FGYKI-52895HexacyclonateIdazoxanIndanorexIndatralineJNJ-7925476LazabemideLeptaclineLomevactoneLR-5182MazindolMeclofenoxateMedifoxamineMefexamideMethamnetamineMethastyridoneMethiopropamineNaphthylaminopropaneNefopamNikethamideNomifensineO-2172OxaprotilinePNU-99,194PRC200-SSRasagilineRauwolscineRubidium chlorideSetazindolTametralineTandamineThiopropamineThiothinoneTraziumUH-232YohimbineMonoamine releasing agentsβ-Me-PEAIofetamine (123I)Metamfepramone5-APDIMethylhexanaminePhenylbiguanideSelegiline8-OH-DPAT2-Methyl-MDA5-APDB5-Methyl-MDA6-APDB6-Methyl-MDAAmiflamineBrephedroneEtolorexFlucetorex4-TFMAMepiprazolepTFMPPTryptamineIndeloxazineViqualineSoRI-9804SoRI-20041BethanidineBretyliumGuanadrelGuanazodineGuanethidineGuanoxan25B-NBOMe25C-NBOMe25D-NBOMe25I-NBOMe25N-NBOMe2C-G-12C-G-22C-G-32C-G-42C-G-52C-G-62C-G-N2C-O-42C-T-22C-T-32C-T-42C-T-72C-T-82C-T-92C-T-132C-T-152C-T-162C-T-172C-T-192C-T-212C-T-282C-TFE2C-TFMAllylescalineDESOXYEscalineIsoproscalineJimscalineMacromerineMescalineMetaescalineMethallylescalineProscalinePsi-2C-T-4Phenylethanolamineα-Methylphenethylaminem-MethylphenethylamineN-Methylphenethylamineo-Methylphenethylaminep-MethylphenethylamineAmphetamines3C-MALBeatriceBromo-DragonFLYGaneshaMMDA-2Psi-DOMZDCM-04Isopropylamphetamine5-EAPB5-MAPB5-MAPDB6-Chloro-MDMA6-EAPB6-MAPB6-MAPDB3,4-MDA (tenamfetamine)3,4-DCADiFMDAPhenterminesCericlamine4-MeMABPHydroxybupropionN-EthylpentedronePhenylalkylpyrrolidines4-MePBP4-MePHP4-MePPPCatecholamines6-OHDAa-Me-DAa-Me-TRAAdrenochromeCiladopaD-DOPADimetofrineFenclonineL-DOPAL-DOPSL-PhenylalanineL-Tyrosinem-TyramineMetaterolMetirosineMethyldopaN,N-DimethyldopamineNordefrinLevonordefrinp-Octopaminep-TyramineAL-LADCafedrineDesvenlafaxineDiphenidineDizocilpineEphenidineETH-LADFluorolintaneIP-LADLysergic acid amideLysergic acid 2-butyl amideLysergic acid 2,4-dimethylazetidideLysergic acid diethylamideMethoxphenidinePARGY-LADPhenibutPRO-LADPronethalolThiamphenicolUWA-101Venlafaxine