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Racemic amphetamine

Central nervous system stimulantPharmaceutical compoundBall-and-stick models of amphetamine enantiomersClinical dataPronunciation Trade namesEvekeo, Adderall, othersOther namesα-methylphenethylamine, β-phenylisopropylamine, thyramineAHFS/Drugs.comMonographMedlinePlusa616004License dataUS DailyMed: AmphetamineDependenceliabilityPhysical: NonePsychological: ModerateAddictionliabilityModerateRoutes ofadministrationMedical: OralRecreational: Oral, insufflation, rectal, intramuscular, intravenousDrug classStimulant; anorectic; norepinephrine-dopamine releasing agentATC codeN06BA01 (WHO) N06BA02 (WHO) N06BA12 (WHO)Physiological dataReceptorsTAAR1, VMAT2, 5HT1AMetabolismCYP2D6, DBH, FMO3Legal statusLegal statusAU: S8 (Controlled drug)BR: Class A3 (Psychoactive drugs)CA: Schedule IDE: Anlage III (Special prescription form required)NZ: Class BUK: Class BUS: Schedule IIUN: Psychotropic Schedule IISE: Förteckning II (in some forms, like Dextroamphetamine and Lisdexamfetamine)Pharmacokinetic dataBioavailabilityOral: ~90%Protein binding16-20%MetabolismCYP2D6, DBH, FMO3Metabolites4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, N-hydroxyamphetamine, benzoic acid, hippuric acid, norephedrine, phenylacetoneOnset of actionIR dosing: 30-45 minutesXR dosing: 1.5–2 hoursElimination half-lifeD-amph: 9–11 hoursL-amph: 11–14 hourspH-dependent: 7–34 hoursDuration of actionIR dosing: 3–6 hoursXR dosing: 8–12 hoursExcretionPrimarily renal;pH-dependent range: 1–75%IdentifiersIUPAC name(RS)-1-phenylpropan-2-amineCAS Number300-62-9PubChemCID3007IUPHAR/BPS4804DrugBankDB00182ChemSpider13852819UNIICK833KGX7EKEGGD07445ChEBICHEBI:2679ChEMBLChEMBL405NIAID ChemDB018564CompTox Dashboard(EPA)DTXSID4022600ECHA InfoCard100.005.543Chemical and physical dataFormulaC9H13NMolar mass135.210 g·mol3D model (JSmol)Interactive imageChiralityRacemic mixtureDensity.936 g/cm at 25 °CMelting point11.3 °C (52.3 °F) Boiling point203 °C (397 °F) at 760 mmHgSMILESNC(C)Cc1ccccc1InChIInChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3Key:KWTSXDURSIMDCE-UHFFFAOYSA-N (verify)Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy; it is also used to treat binge eating disorder in the form of lisdexamfetamine.

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