CHEBI:27732 - caffeine

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ChEBI Name caffeine
ChEBI ID CHEBI:27732
Definition A trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3295, CHEBI:41472, CHEBI:22982
Supplier Information eMolecules:712466
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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. Caffeine acts by blocking 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 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. 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 also an outlier as its use is seen as socially acceptable in most cultures with it even being encouraged. 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. It may confer a modest protective effect against some diseases, including Parkinson's disease. Some people experience sleep disruption or anxiety if they consume caffeine, 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. 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. 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). Caffeine is classified by the U.S. Food and Drug Administration (FDA) 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. 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. A cup of coffee contains 80–175 mg of caffeine, depending on what "bean" (seed) is used, how it is roasted, and how it is prepared (e.g., drip, percolation, or espresso). 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.
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Formula C8H10N4O2
Net Charge 0
Average Mass 194.19076
Monoisotopic Mass 194.08038
InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChIKey RYYVLZVUVIJVGH-UHFFFAOYSA-N
SMILES Cn1cnc2n(C)c(=O)n(C)c(=O)c12
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Theobroma cacao (NCBI:txid3641) See: DOI
Camellia sinensis (NCBI:txid4442) See: PubMed
Claviceps sorghicola (NCBI:txid83213) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
An EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a phosphoric diester hydrolase (EC 3.1.4.*).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine.
ryanodine receptor agonist
A ryanodine receptor modulator which activates the receptor. Ryanodine receptors (RyRs) act as selective ion channels, modulating the release of calcium. Activating the receptors causes the release of calcium, so depleting internal calcium and ultimately preventing further muscle contraction.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
adenosine A2A receptor antagonist
An antagonist at the A2A receptor.
food additive
Any substance which is added to food to preserve or enhance its flavour and/or appearance.
adenosine receptor antagonist
An antagonist at any adenosine receptor.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
mutagen
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
diuretic
An agent that promotes the excretion of urine through its effects on kidney function.
food additive
Any substance which is added to food to preserve or enhance its flavour and/or appearance.
adjuvant
Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself.
central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing caffeine (CHEBI:27732) has role adenosine A2A receptor antagonist (CHEBI:53121)
caffeine (CHEBI:27732) has role adenosine receptor antagonist (CHEBI:71232)
caffeine (CHEBI:27732) has role adjuvant (CHEBI:60809)
caffeine (CHEBI:27732) has role central nervous system stimulant (CHEBI:35337)
caffeine (CHEBI:27732) has role diuretic (CHEBI:35498)
caffeine (CHEBI:27732) has role EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor (CHEBI:50925)
caffeine (CHEBI:27732) has role EC 3.1.4.* (phosphoric diester hydrolase) inhibitor (CHEBI:50218)
caffeine (CHEBI:27732) has role environmental contaminant (CHEBI:78298)
caffeine (CHEBI:27732) has role food additive (CHEBI:64047)
caffeine (CHEBI:27732) has role fungal metabolite (CHEBI:76946)
caffeine (CHEBI:27732) has role geroprotector (CHEBI:176497)
caffeine (CHEBI:27732) has role human blood serum metabolite (CHEBI:85234)
caffeine (CHEBI:27732) has role mouse metabolite (CHEBI:75771)
caffeine (CHEBI:27732) has role mutagen (CHEBI:25435)
caffeine (CHEBI:27732) has role plant metabolite (CHEBI:76924)
caffeine (CHEBI:27732) has role psychotropic drug (CHEBI:35471)
caffeine (CHEBI:27732) has role ryanodine receptor agonist (CHEBI:67114)
caffeine (CHEBI:27732) has role xenobiotic (CHEBI:35703)
caffeine (CHEBI:27732) is a purine alkaloid (CHEBI:26385)
caffeine (CHEBI:27732) is a trimethylxanthine (CHEBI:27134)
Incoming 8-(3-chlorostyryl)caffeine (CHEBI:53115) has functional parent caffeine (CHEBI:27732)
caffeine monohydrate (CHEBI:31332) has part caffeine (CHEBI:27732)
sodium caffeine benzoate (CHEBI:32140) has part caffeine (CHEBI:27732)
IUPAC Name
1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
Synonyms Sources
1,3,7-trimethyl-2,6-dioxopurine ChemIDplus
1,3,7-trimethylpurine-2,6-dione IUPHAR
1,3,7-Trimethylxanthine KEGG COMPOUND
1,3,7-trimethylxanthine NIST Chemistry WebBook
1-methyltheobromine ChemIDplus
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion NIST Chemistry WebBook
7-methyltheophylline NIST Chemistry WebBook
anhydrous caffeine KEGG DRUG
cafeína ChemIDplus
caféine ChEBI
CAFFEINE PDBeChem
Caffeine KEGG COMPOUND
caffeine UniProt
Coffein ChemIDplus
guaranine IUPHAR
Koffein ChemIDplus
mateína ChemIDplus
methyltheobromine IUPHAR
teína ChEBI
Thein ChemIDplus
theine NIST Chemistry WebBook
Manual Xrefs Databases
1-3-7-TRIMETHYLXANTHINE MetaCyc
463 DrugCentral
C00001492 KNApSAcK
C07481 KEGG COMPOUND
Caffeine Wikipedia
CFF PDBeChem
D00528 KEGG DRUG
DB00201 DrugBank
HMDB0001847 HMDB
LSM-2026 LINCS
View more database links
Registry Numbers Types Sources
103040 Gmelin Registry Number Gmelin
17705 Reaxys Registry Number Reaxys
58-08-2 CAS Registry Number KEGG COMPOUND
58-08-2 CAS Registry Number NIST Chemistry WebBook
58-08-2 CAS Registry Number ChemIDplus
Citations
Last Modified
20 September 2021
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag