caffeine
Chemical compound used as a stimulant
Also known as guaranine · methyltheobromine · 7-methyltheophylline · theine · 1,3,7-trimethyl-2,6-dioxopurine · 1,3,7-trimethylxanthine
- Formula
- C₈H₁₀N₄O₂
1
- C₈H₁₀N₄O₂
- Mass
- 194.08 Da
1
- , 194.0804 Da
- 194.08 Da
- Melting point
- 234°C
- , 235°C
1
- Density
- 1.23 g/cm³
Overview
Chemistry
All data
258 statements · 62% with external sources · numbers in brackets are citations
- Canonical SMILES
- CN1C=NC2=C1C(=O)N(C(=O)N2C)C
1
- CN1C=NC2=C1C(=O)N(C(=O)N2C)C
- PKa
- 14
- 10.4 temperature: 40°C
1
- Electric dipole moment
- 3.64 debye
- MCN code
- 2939.30.10
- Physically interacts with
- Adenosine A1 receptor subject has role: antagonist
1
- Adenosine A2a receptor subject has role: antagonist
1
- Adenosine A2b receptor subject has role: antagonist
1
- Adenosine A3 receptor subject has role: antagonist
1
- Inositol 1,4,5-trisphosphate receptor type 1 subject has role: antagonist
1
- Ryanodine receptor 1 subject has role: antagonist
1
- Ryanodine receptor 2 subject has role: antagonist
1
- Ryanodine receptor 3 subject has role: antagonist
1
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- taste receptor type 2 subject has role: agonist
- Adenosine A1 receptor subject has role: antagonist
- Found in taxon
- Senegalia catechu
- guarana plant
9
Sources- 1.Stated in A quantitative method for the analysis of xanthine alkaloids inPaullinia cupana (guarana) by capillary column gas chromatography
- 2.Stated in Herbal Products as Mouthwash
- 3.Stated in HPLC determination of caffeine and theophylline in Paullinia cupana Kunth (guarana) and Cola spp. samples
- 4.Stated in Theobromine, theophylline, and caffeine in 42 samples and products of Guaraná (Paullinia cupana, Sapindaceae)
- 5.Stated in Guaraná (Paullinia cupana) rewards seed dispersers without intoxicating them by caffeine
- 6.Stated in Liquid Chromatographic Determination of Methylxanthines and Catechins in Herbal Preparations Containing Guaraná
- yerba mate
14
Sources- 1.Stated in Mate substitutes or adulterants: study of xanthine content
- 2.Stated in High-performance capillary electrophoresis analysis of mate infusions prepared from stems and leaves of Ilex paraguariensis using automated micellar electrokinetic capillary chromatography
- 3.Stated in Trigonelline in coffee
- 4.Stated in Purine metabolism and the biosynthesis of caffeine in maté leaves
- 5.Stated in Chlorogenic acids and purine alkaloids contents of Maté (Ilex paraguariensis) leaf and beverage
- 6.Stated in Studies on mate drinking
- Ilex argentina
- Ilex brevicuspis
- Ilex theezans
- Ilex dumosa
- Ilex microdonta
Show 52 moreShow less
- Ilex pseudobuxus
- Aspalathus linearis
- Coffea arabica
33
Sources- 1.Stated in Coffee, Tea, Cocoa
- 2.Stated in Chlorogensäure in Semen Coffeae und ihre Veränderung beim Röstprozeß. 3. Mitteilung
- 3.Stated in Reproducibility of the determination of caffeine in coffee by micellar electrokinetic capillary chromatography
- 4.Stated in Biotransformation of theobromine to caffeine in suspension and polyurethane foam immobilized coffee (Coffea arabica L.) cells
- 5.Stated in Genetically decaffeinated coffee
- 6.Stated in Purine alkaloid formation in buds and developing leaflets of Coffea arabica: Expression of an optimal defence strategy?
- Camellia irrawadiensis
- Scurrula atropurpurea
- Bidens pilosa
- Camellia multisepala
- Camellia japonica
1
- Camellia ptilophylla
- Camellia oleifera
1
- Camellia sasanqua
1
- Camellia vernalis
1
- Citrus grandis
2
Sources- 1.Stated in Identification of caffeine in citrus flowers and leaves
- 2.Stated in Caffeine in Citrus flowers
- pomelo
2
Sources- 1.Stated in Identification of caffeine in citrus flowers and leaves
- 2.Stated in Caffeine in Citrus flowers
- Citrus reticulata
- Claviceps sorghicola
1
- Coffea bengalensis
- Coffea canephora
2
Sources- 1.Stated in Caffeine, trigonelline, chlorogenic acids and sucrose diversity in wild Coffea arabica L. and C. canephora P. accessions
- 2.Stated in Development of an HPLC/Diode-Array Detector Method for Simultaneous Determination of Trigonelline, Nicotinic Acid, and Caffeine in Coffee
- Coffea eugenioides
- Coffea homollei
- Coffea kianjavatensis
2
- Coffea lancifolia
- Coffea salvatrix
- Cola nitida
3
Sources- 1.Stated in Behavioral effects resulting from sub-chronic treatment of rats with extract of fresh stabilized cola seeds
- 2.Stated in Study of Caffein - Catechin Association in Lyophilized Fresh Seeds and in Stabilized Extract of Cola nitida
- 3.Stated in Content of polyphenolic compounds in the Nigerian stimulants Cola nitida ssp. alba, Cola nitida ssp. rubra A. Chev, and Cola acuminata Schott & Endl and their antioxidant capacity
- Festuca pratensis
1
- Herrania albiflora
- Herrania balaensis
- Herrania cuatrecasana
- Herrania nitida
- Herrania purpurea
- Ilex guayusa
- Murraya paniculata
1
- Paramuricea clavata
- Pausinystalia
- Sinomenium acutum
- Theobroma angustifolium
- Theobroma cacao
11
Sources- 1.Stated in Extraction of purine alkaloids from cocoa tissues and determination by high-performance liquid chromatography
- 2.Stated in Purine alkaloids in seeds ofTheobroma species from the Amazon
- 3.Stated in Simple method for the determination of alkaloids in cocoa using paper chromatography and UV spectrometry
- 4.Stated in Purine alkaloid distribution with Herrania and Theorbroma
- 5.Stated in Identification of procyanidins in cocoa (Theobroma cacao) and chocolate using high-performance liquid chromatography/mass spectrometry
- 6.Stated in Purine Alkaloid Production and Accumulation in Cocoa Callus and Suspension Cultures
- Theobroma mammosum
- Theobroma simiarum
- Theobroma grandiflorum
- Cola acuminata
- Vincetoxicum hirsutum (Michx.) Britton (1894) non (Wall.) Kuntze (1891)
1
- Trewia nudiflora
- Homo sapiens
- house mouse
3
Sources- 1.Stated in Depressing effects of caffeine at crayfish neuromuscular synapses I. Dosage response and Ca++ gradient effects
- 2.Stated in Does caffeine alter muscle carbohydrate and fat metabolism during exercise?
- 3.Stated in Caffeine inhibits InsP3 responses and capacitative calcium entry in canine pulmonary arterial smooth muscle cells
- Citrus glauca
1
- Camellia kissi
1
- Coffea benghalensis
- Theobroma speciosum
- Strobilanthes crispa
- Camellia
- Camellia sinensis var. sinensis
1
- Isomeric SMILES
- Cn1c(=O)c2c(ncn2C)n(C)c1=O
On other databases
104 identifiers linking caffeine across the web's reference databases
- ABC News topic IDcaffeine
- AGROVOC IDc_1183
- Article ID in the Lithuanian Universal Encyclopedia Onlinekofeinas
- ATC codeN06BC01
- AUSNUT food ID14B10182
- BBC Things ID85a85f6f-421d-4ed3-87e4-4b93ca135e36
- Bibliothèque nationale de France ID12080052b
- BNCF Thesaurus ID12569
- CA PROP 65 IDcaffeine
- CAMEO Chemicals ID19945
- CAS Registry Number58-08-2
- ChEBI ID27732
- ChEMBL IDCHEMBL113
- ChemSpider ID2424
- CosIng number32304
- DeCS ID2143
- Dewey Decimal Classification641.26
- DrugBank IDDB00201
- DrugCentral ID463
- DSSTOX compound identifierDTXCID40232
- DSSTox substance IDDTXSID0020232
- EC number200-362-1
- ECHA Substance Infocard ID100.000.329
- Encyclopædia Britannica Online IDscience/caffeine
- Encyclopedia of China (Third Edition) ID (2026)4OqNPZ
- Encyclopedia of China (Third Edition) old ID (2021)494150
- Fandom article IDde.drogen:Coffein
- FL number16.016
- Freebase ID/m/01_7l
- Gmelin number103040
- GND ID4010359-6
- Great Norwegian Encyclopedia IDkoffein
- Great Russian Encyclopedia Online ID (2017)2104242
- Guide to Pharmacology Ligand ID407
- HCIS ID795
- Hrvatska enciklopedija ID32232
- HSDB ID36
- Human Metabolome Database IDHMDB0001847
- ICSC ID0405
- InChIInChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
- InChIKeyRYYVLZVUVIJVGH-UHFFFAOYSA-N
- J9U entity ID987007293675905171
- KBpedia IDCaffeine
- KEGG IDD00528
- KNApSAcK IDC00001492
- Krugosvet article (archived)biologiya/kofein
- LEM IDLEM201009766
- Lex IDkoffein
- Library of Congress Authorities IDsh85018686
- MassBank accession IDMSBNK-Eawag-EA030311
- MeSH descriptor IDD002110
- MeSH tree codeD03.132.960.175
- Microsoft Academic ID (discontinued)2778500429
- Museum-digital tag ID51394
- NALT ID21000
- Namuwiki ID카페인
- Natural Product Atlas IDNPA007904
- NDF-RT IDN0000145919
- NDL Authority ID00564463
- New York Times topic IDsubject/caffeine
- NicoNicoPedia word article IDカフェイン
- NL CR AUT IDph318951
- NMRShiftDB structure ID10016316
- NSC number5036
- OmegaWiki Defined Meaning508638
- Open Food Facts ingredient IDcaffeine
- Open Library subject IDcaffeine
- OpenAlex IDC2778500429
- PatientsLikeMe treatment IDcaffeine
- PDB ligand IDCFF
- PDB structure ID1L5Q
- PesticideInfo chemical IDPRI1805
- Pixiv Encyclopedia IDカフェイン
- PM20 ware ID143117
- Probes And Drugs IDPD002448
- Proleksis enciklopedija ID31690
- PubChem CID2519
- Quora topic IDCaffeine
- Reaxys registry number17705
- Römpp online IDRD-03-02269
- RTECS numberEV6475000
- RxNorm CUI1886
- ScienceDirect topic IDmedicine-and-dentistry/caffeine
- SPLASHsplash10-0002-0900000000-b112e4e059e1ecf98c5f
- Store medisinske leksikon IDkoffein
- SureChEMBL ID5671
- Treccani IDcaffeina
- Treccani Vocabulary IDcaffeina
- Treccani's Enciclopedia Italiana IDcaffeina
- UK Parliament thesaurus ID429747