Caffeine

Clinical data
Pronunciation	/kæˈfiːn, ˈkæfiːn/
Synonyms	Guaranine Methyltheobromine 1,3,7-Trimethylxanthine 7-methyltheophylline Theine
AHFS/Drugs.com	Monograph
Pregnancy category	AU: A
Dependence liability	Physical: low–moderate Psychological: low
Addiction liability	Low / none
Routes of administration	By mouth, insufflation, enema, rectal, intravenous
Drug class	Stimulant
ATC code	N06BC01 (WHO) D11AX26, V04CG30
Legal status
Legal status	CA: Unscheduled UK: General sales list (GSL, OTC) US: Unscheduled
Pharmacokinetic data
Bioavailability	99%
Protein binding	25–36%
Metabolism	Primary: CYP1A2 Minor: CYP2E1,CYP3A4, CYP2C8,CYP2C9
Metabolites	Paraxanthine (84%) Theobromine (12%) Theophylline (4%)
Onset of action	~1 hour
Elimination half-life	Adults: 3–7 hours Infants (full term): 8 hours Infants (premature): 100 hours
Duration of action	3–4 hours
Excretion	Urine (100%)
Identifiers
IUPAC name 1,3,7-Trimethylpurine-2,6-dione
CAS Number	58-08-2 Y
PubChem CID	2519
IUPHAR/BPS	407
DrugBank	DB00201 Y
ChemSpider	2424 Y
UNII	3G6A5W338E
KEGG	D00528 Y
ChEBI	CHEBI:27732 Y
ChEMBL	ChEMBL113 Y
PDB ligand	CFF (PDBe, RCSB PDB)
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C8H10N4O2
Molar mass	194.19 g·mol−1
3D model (JSmol)	Interactive image
Density	1.23 g/cm3
Melting point	235 to 238 °C (455 to 460 °F) (anhydrous)
SMILES CN1C=NC2=C1C(=O)N(C(=O)N2C)C
InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 Key:RYYVLZVUVIJVGH-UHFFFAOYSA-N Y

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Coffee plant (Coffea arabica), with fruits. The fruits, which are used to make coffee, contain caffeine.

Caffeine is a central nervous system (CNS) stimulant. It is in the methylxanthine class. It is found in many plants, and is used in drinks like coffee, some teas, some soft drinks, and energy drinks. It can be harmful for both humans and animals if a large amount is consumed. If a person ate 10-13 grams of caffeine quickly, between 80 and 100 cups of coffee, they would overdose and may die. It is the world's most popular psychoactive drug, and is legal in nearly all of the world.