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Caffeinated

Central nervous system stimulantPharmaceutical compoundClinical dataPronunciation Other namesGuaranineMethyltheobromine1,3,7-Trimethylxanthine7-methyltheophylline TheineAHFS/Drugs.comMonographLicense dataUS DailyMed: CaffeinePregnancycategoryAU: ADependenceliabilityPhysical: Low–moderate (9–30%) Psychological: Low–moderateAddictionliabilityNoneRoutes ofadministrationCommon: By mouth Medical: IntravenousUncommon: Insufflation, rectal, transdermal, topical, buccal, sublingual, inhalationDrug classStimulant;Adenosinergic;Eugeroic;Nootropic;Anxiogenic; Analeptic; PDE inhibitor;DiureticATC codeN06BC01 (WHO) D11AX26 (WHO), V04CG30 (WHO)Legal statusLegal statusAU: UnscheduledBR: UnscheduledCA: UnscheduledDE: UnscheduledNZ: UnscheduledUK: General sales list (GSL, OTC)US: UnscheduledUN: UnscheduledCN: OTCSE: Unscheduled In general legal for all usesPharmacokinetic dataBioavailability99%Protein binding10–36%MetabolismPrimary: CYP1A2Minor: CYP2E1, CYP3A4,CYP2C8, CYP2C9MetabolitesParaxanthine 84%Theobromine 12%Theophylline 4%Onset of action45 minutes–1 hourElimination half-lifeAdults: 3–7 hoursInfants (full term): 8 hoursInfants (premature): 100 hoursDuration of action3–4 hoursExcretionUrine (100%)IdentifiersIUPAC name1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dioneCAS Number58-08-2PubChemCID2519IUPHAR/BPS407DrugBankDB00201ChemSpider2424UNII3G6A5W338EKEGGD00528ChEBICHEBI:27732ChEMBLChEMBL113NIAID ChemDBnonePDB ligandCFF (PDBe, RCSB PDB)CompTox Dashboard(EPA)DTXSID0020232ECHA InfoCard100.000.329Chemical and physical dataFormulaC8H10N4O2Molar mass194.194 g·mol3D model (JSmol)Interactive imageDensity1.23 g/cmMelting point235 to 238 °C (455 to 460 °F) (anhydrous)SMILESCN1C=NC2=C1C(=O)N(C(=O)N2C)CInChIInChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3Key:RYYVLZVUVIJVGH-UHFFFAOYSA-NData pageCaffeine (data page)Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class and is the most commonly consumed psychoactive drug globally.

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