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caffeine

File:Caffeine_structure.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ60235· pop 97· linked from 3,330 articles

Also known as methyltheobromine, 1,3,7-trimethyl-2,6-dioxopurine, 1,3,7-trimethylxanthine, theine, 7-methyltheophylline, 1-methyltheobromine, guaranine, 1,3,7-trimethylpurine-2,6-dione

Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class and is the most commonly consumed psychoactive substance globally. It is mainly used for its eugeroic (wakefulness promoting), ergogenic (physical performance-enhancing), or nootropic (cognitive-enhancing) properties; it is also used recreationally or in social settings. Caffeine acts by blocking the binding of adenosine at a number of adenosine receptor types, inhibiting the centrally depressant effects of adenosine and enhancing the release of acetylcholine. Caffeine has a three-dimensional structure similar to

OverviewAI-generated

Caffeine is a chemical compound with the formula C₈H₁₀N₄O₂. Its IUPAC name is 1,3,7-trimethylpurine-2,6-dione. The substance has a mass of 194.08037556 and a density of 1.23. It melts at 235 and sublimes at 180. The pKa is 14, and the electric dipole moment is 3.64.

Chemical properties include an xlogp of -0.1 and a topological polar surface area of 58.4. The molecule has zero hydrogen bond donors and three hydrogen bond acceptors, with a charge of 0. The canonical SMILES representation is CN1C=NC2=C1C(=O)N(C(=O)N2C)C.

Caffeine is referenced by 3,330 other encyclopedia articles. A PubMed query for caffeine yields 42,555 results. The MCN code for the compound is 2939.30.10.

Synthesized by Vinony from 25 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.image
Caffeine structure.svg
Drug.image_class
skin-invert-image
Drug.width
187
Drug.alt
2D structure of caffeine
Drug.image_class2
bg-transparent
Drug.alt2
3D structure of caffeine
Drug.imageL
Caffeine molecule ball from xtal (1).png
Drug.image_classL
bg-transparent
Drug.imageR
Caffeine molecule spacefill from xtal (1).png
Drug.image_classR
bg-transparent
Drug.DailyMedID
Caffeine
Drug.pregnancy_AU
A
Drug.dependency_liability
Physical: Low–moderate (9–30%) Psychological: Low–moderate
Drug.addiction_liability
Low (9%)
Drug.routes_of_administration
Common: By mouth Medical: Intravenous Uncommon: Insufflation, rectal, transdermal, topical, buccal, sublingual
Drug.class
Stimulant;Adenosinergic; Eugeroic;Nootropic;Anxiogenic; Analeptic; PDE inhibitor;Diuretic
Drug.ATC_prefix
N06B
Drug.ATC_suffix
C01

via Wikipedia infobox

Chemical data

Formula
C8H10N4O2
Molecular weight
194.19 g/mol
IUPAC name
1,3,7-trimethylpurine-2,6-dione
SMILES
CN1C=NC2=C1C(=O)N(C(=O)N2C)C
InChIKey
RYYVLZVUVIJVGH-UHFFFAOYSA-N
XLogP
-0.1
Polar surface area
58.4 Ų
H-bond donors
0
H-bond acceptors
3
Formal charge
0

via PubChem

Research

42,555 papers

via PubMed

~62 min read

Encyclopedic overview

69 sections
Contents
  • Uses
  • Medical
  • Enhancing performance
  • Cognitive performance
  • Physical performance
  • Specific populations
  • Adults
  • Children
  • Adolescents
  • Pregnancy and breastfeeding
  • Adverse effects{{anchor|Side_effects}}
  • Physiological
  • Psychological
  • Reinforcement disorders
  • Addiction
  • Dependence and withdrawal
  • Risk of other diseases
  • Energy crash
  • Overdose
  • Energy drinks
  • Severe intoxication
  • Lethal dose
  • Interactions
  • Alcohol
  • Smoking
  • Birth control
  • Medications
  • Pharmacology
  • Pharmacodynamics
  • Receptor and ion channel targets
  • Effects on striatal dopamine
  • Enzyme targets
  • Pharmacokinetics
  • Chemistry
  • See also
  • Synthesis
  • Decaffeination
  • Detection in body fluids
  • Analogs
  • Precipitation of tannins
  • Commercial sources
  • Natural occurrence
  • Products
  • Beverages
  • Coffee
  • Tea
  • Soft drinks and energy drinks
  • Other beverages
  • Cacao solids
  • Chocolate
  • Tablets
  • Other oral products
  • Inhalants
  • Combinations with other drugs
  • History
  • Discovery and spread of use
  • Chemical identification, isolation, and synthesis
  • Historic regulations
  • Society and culture
  • Regulations
  • United States
  • Consumption
  • Religions
  • Other organisms
  • Research
  • See also
  • References
  • Bibliography
  • External links

Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class and is the most commonly consumed psychoactive substance globally. It is mainly used for its eugeroic (wakefulness promoting), ergogenic (physical performance-enhancing), or nootropic (cognitive-enhancing) properties; it is also used recreationally or in social settings. Caffeine acts by blocking the binding of adenosine at a number of adenosine receptor types, inhibiting the centrally depressant effects of adenosine and enhancing the release of acetylcholine. Caffeine has a three-dimensional structure similar to that of adenosine, which allows it to bind and block its receptors. Caffeine also increases cyclic AMP levels through nonselective inhibition of phosphodiesterase, increases calcium release from intracellular stores, and antagonizes GABA receptors, although these mechanisms typically occur at concentrations beyond usual human consumption.

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 and helps to protect them against herbivores and from competition by preventing the germination of nearby seeds, as well as encouraging consumption by select animals such as honey bees. The most common sources of caffeine for human consumption are the tea leaves of the Camellia sinensis plant and the coffee bean, the seed of the Coffea plant. Some people 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 tea, coffee, and cola, are consumed globally in high volumes. In 2020, almost 10 million tonnes of coffee beans were consumed globally. Caffeine is the world's most widely consumed psychoactive drug. Unlike most other psychoactive substances, caffeine remains largely unregulated and legal in nearly all parts of the world. Caffeine is seen as socially acceptable in most cultures and is encouraged in some.

Excerpted from Wikipedia’s “caffeine” article, available under the CC BY-SA 4.0 licence.

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