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Central nervous system stimulant / From Wikipedia, the free encyclopedia

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Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class.[12] It is mainly used recreationally as a cognitive enhancer, increasing alertness and attentional performance.[13][14] Caffeine acts by blocking binding of adenosine to the adenosine A1 receptor, which enhances release of the neurotransmitter acetylcholine.[15] Caffeine has a three-dimensional structure similar to that of adenosine, which allows it to bind and block its receptors.[16] Caffeine also increases cyclic AMP levels through nonselective inhibition of phosphodiesterase.[17]

Quick facts: Clinical data, Pronunciation, Other names, AH...
2D structure of caffeine
3D structure of caffeine
Clinical data
Pronunciation/kæˈfn, ˈkæfn/
Other namesGuaranine
7-methyltheophylline[1] Theine
  • AU: A
Physical: low–moderate[2][3][4][5]
Psychological: low[6]
Routes of
By mouth, insufflation, enema, rectal, intravenous
Drug classStimulant
ATC code
Legal status
Legal status
  • AU: Unscheduled
  • CA: Unscheduled
  • DE: Unscheduled
  • NZ: Unscheduled
  • UK: General sales list (GSL, OTC)
  • US: Unscheduled
  • In general: Legal for recreational use in most countries
Pharmacokinetic data
Protein binding25–36%[8]
MetabolismPrimary: CYP1A2[8]
Minor: CYP2E1,[8] CYP3A4,[8]
CYP2C8,[8] CYP2C9[8]
MetabolitesParaxanthine (84%)
Theobromine (12%)
Theophylline (4%)
Onset of action45 minutes–1 hour[7][9]
Elimination half-lifeAdults: 3–7 hours[8]
Infants (full term): 8 hours[8]
Infants (premature): 100 hours[8]
Duration of action3–4 hours[7]
ExcretionUrine (100%)
  • 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione
CAS Number
PubChem CID
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.329 Edit this at Wikidata
Chemical and physical data
Molar mass194.194 g·mol−1
3D model (JSmol)
Density1.23 g/cm3
Melting point235 to 238 °C (455 to 460 °F) (anhydrous)[10][11]
  • CN1C=NC2=C1C(=O)N(C(=O)N2C)C
  • InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
Data page
Caffeine (data page)

Caffeine is a bitter, white crystalline purine, a methylxanthine alkaloid, and is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, fruits, nuts, or leaves of a number of plants native to Africa, East Asia and South America,[18] and helps to protect them against herbivores and from competition by preventing the germination of nearby seeds,[19] as well as encouraging consumption by select animals such as honey bees.[20] The best-known source of caffeine is the coffee bean, the seed of the Coffea plant. People may drink beverages containing caffeine to relieve or prevent drowsiness and to improve cognitive performance. To make these drinks, caffeine is extracted by steeping the plant product in water, a process called infusion. Caffeine-containing drinks, such as coffee, tea, and cola, are consumed globally in high volumes. In 2020, almost 10 million tonnes of coffee beans were consumed globally.[21] Caffeine is the world's most widely consumed psychoactive drug.[22][23] Unlike most other psychoactive substances, caffeine remains largely unregulated and legal in nearly all parts of the world. Caffeine is also an outlier as its use is seen as socially acceptable in most cultures and even encouraged in others.

Caffeine has both positive and negative health effects. It can treat and prevent the premature infant breathing disorders bronchopulmonary dysplasia of prematurity and apnea of prematurity. Caffeine citrate is on the WHO Model List of Essential Medicines.[24] It may confer a modest protective effect against some diseases,[25] including Parkinson's disease.[26] Some people experience sleep disruption or anxiety if they consume caffeine,[27] but others show little disturbance. Evidence of a risk during pregnancy is equivocal; some authorities recommend that pregnant women limit caffeine to the equivalent of two cups of coffee per day or less.[28][29] Caffeine can produce a mild form of drug dependence – associated with withdrawal symptoms such as sleepiness, headache, and irritability – when an individual stops using caffeine after repeated daily intake.[2][4][6] Tolerance to the autonomic effects of increased blood pressure and heart rate, and increased urine output, develops with chronic use (i.e., these symptoms become less pronounced or do not occur following consistent use).[30]

Caffeine is classified by the US Food and Drug Administration as generally recognized as safe. Toxic doses, over 10 grams per day for an adult, are much higher than the typical dose of under 500 milligrams per day.[31] The European Food Safety Authority reported that up to 400 mg of caffeine per day (around 5.7 mg/kg of body mass per day) does not raise safety concerns for non-pregnant adults, while intakes up to 200 mg per day for pregnant and lactating women do not raise safety concerns for the fetus or the breast-fed infants.[32] A cup of coffee contains 80–175 mg of caffeine, depending on what "bean" (seed) is used, how it is roasted (darker roasts have less caffeine), and how it is prepared (e.g., drip, percolation, or espresso).[33] Thus it requires roughly 50–100 ordinary cups of coffee to reach the toxic dose. However, pure powdered caffeine, which is available as a dietary supplement, can be lethal in tablespoon-sized amounts.