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Record Information
Version1.0
Created at2006-02-16 08:53:46 UTC
Updated at2020-09-11 01:14:39 UTC
NP-MRD IDNP0000009
Secondary Accession NumbersNone
Natural Product Identification
Common NameCaffeine
DescriptionCaffeine, also known as coffein or mateina, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. When considered comprehensively, findings from experimental and epidemiologic studies converge to show that BP remains reactive to the pressor effects of caffeine in the diet. Caffeine is a drug which is used for management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants. Caffeine is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, caffeine participates in a number of enzymatic reactions. In particular, caffeine can be converted into paraxanthine and formaldehyde through its interaction with the enzyme cytochrome P450 1A2. In addition, caffeine can be converted into theobromine and formaldehyde; which is catalyzed by the enzymes cytochrome P450 1A2 and cytochrome P450 2E1. In humans, caffeine is involved in caffeine metabolism. Caffeine is a bitter and odorless tasting compound. Outside of the human body, Caffeine is found, on average, in the highest concentration within a few different foods, such as arabica coffee, coffee, and tea and in a lower concentration in frozen yogurts, coffee mocha, and other beverages. Caffeine has also been detected, but not quantified in, several different foods, such as common chokecherries, garden onions, hushpuppies, cherry tomato, and florida pompano. This could make caffeine a potential biomarker for the consumption of these foods. Caffeine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1,3,7-Trimethyl-2,6-dioxopurineChEBI
1,3,7-Trimethylpurine-2,6-dioneChEBI
1,3,7-TrimethylxanthineChEBI
1-MethyltheobromineChEBI
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dionChEBI
7-MethyltheophyllineChEBI
Anhydrous caffeineChEBI
CafeinaChEBI
CafeineChEBI
CoffeinChEBI
GuaranineChEBI
KoffeinChEBI
MateinaChEBI
MethyltheobromineChEBI
TeinaChEBI
TheinChEBI
TheineChEBI
RespiaKegg
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dioneHMDB
1-Methyl-theobromineHMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dioneHMDB
7-Methyl theophyllineHMDB
Anhydrous caffeine (JP15)HMDB
HycomineHMDB
LanorinalHMDB
MethyltheobromideHMDB
Methylxanthine theophyllineHMDB
Monohydrate caffeineHMDB
PropoxypheneHMDB
Merck dura brand OF caffeineHMDB
Thompson brand 1 OF caffeineHMDB
Bristol-myers squibb brand OF caffeineHMDB
CaffedrineHMDB
DexitacHMDB
Percoffedrinol NHMDB
Pierre fabre brand OF caffeineHMDB
Republic drug brand OF caffeineHMDB
Thompson brand 2 OF caffeineHMDB
VivarinHMDB
Coffeinum NHMDB
Coffeinum purrumHMDB
DurvitanHMDB
GlaxoSmithKline brand OF caffeineHMDB
No dozHMDB
PercutaféineHMDB
Quick-pepHMDB
Seid brand OF caffeineHMDB
Berlin-chemie brand OF caffeineHMDB
Passauer brand OF caffeineHMDB
Quick pepHMDB
QuickPepHMDB
Chemical FormulaC8H10N4O2
Average Molecular Weight194.1906
Monoisotopic Molecular Weight194.080375584
IUPAC Name1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Namecaffeine
CAS Registry Number58-08-2
SMILES
CN1C=NC2=C1C(=O)N(C)C(=O)N2C
InChI Identifier
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChI KeyRYYVLZVUVIJVGH-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesAnimalia
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • Purinone
  • 6-oxopurine
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Urea
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point238 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility21.6 mg/mL at 25 °CNot Available
LogP-0.07HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP-0.24ALOGPS
logP-0.55ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.44 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity49.83 m³·mol⁻¹ChemAxon
Polarizability18.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0001847
DrugBank IDDB00201
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002100
KNApSAcK IDC00001492
Chemspider ID2424
KEGG Compound IDC07481
BioCyc ID1-3-7-TRIMETHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkCaffeine
METLIN ID1455
PubChem Compound2519
PDB IDNot Available
ChEBI ID27732
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Miyake Y, Sakaguchi K, Iwasaki Y, Ikeda H, Makino Y, Kobashi H, Araki Y, Ando M, Kita K, Shiratori Y: New prognostic scoring model for liver transplantation in patients with non-acetaminophen-related fulminant hepatic failure. Transplantation. 2005 Oct 15;80(7):930-6. [PubMed:16249741 ]
  3. Wilkinson SC, Maas WJ, Nielsen JB, Greaves LC, van de Sandt JJ, Williams FM: Interactions of skin thickness and physicochemical properties of test compounds in percutaneous penetration studies. Int Arch Occup Environ Health. 2006 May;79(5):405-13. Epub 2006 Jan 25. [PubMed:16435152 ]
  4. Spiller HA, Winter ML, Klein-Schwartz W, Bangh SA: Efficacy of activated charcoal administered more than four hours after acetaminophen overdose. J Emerg Med. 2006 Jan;30(1):1-5. [PubMed:16434328 ]
  5. Ayotte P, Dewailly E, Lambert GH, Perkins SL, Poon R, Feeley M, Larochelle C, Pereg D: Biomarker measurements in a coastal fish-eating population environmentally exposed to organochlorines. Environ Health Perspect. 2005 Oct;113(10):1318-24. [PubMed:16203240 ]
  6. Shah S, Budev M, Blazey H, Fairbanks K, Mehta A: Hepatic veno-occlusive disease due to tacrolimus in a single-lung transplant patient. Eur Respir J. 2006 May;27(5):1066-8. [PubMed:16707401 ]
  7. Larson AM, Polson J, Fontana RJ, Davern TJ, Lalani E, Hynan LS, Reisch JS, Schiodt FV, Ostapowicz G, Shakil AO, Lee WM: Acetaminophen-induced acute liver failure: results of a United States multicenter, prospective study. Hepatology. 2005 Dec;42(6):1364-72. [PubMed:16317692 ]
  8. Septer S, Thompson ES, Willemsen-Dunlap A: Anesthesia concerns for children with tuberous sclerosis. AANA J. 2006 Jun;74(3):219-25. [PubMed:16786916 ]
  9. Horrigan LA, Kelly JP, Connor TJ: Immunomodulatory effects of caffeine: friend or foe? Pharmacol Ther. 2006 Sep;111(3):877-92. Epub 2006 Mar 15. [PubMed:16540173 ]
  10. Rodrigues IM, Klein LC: Boiled or filtered coffee? Effects of coffee and caffeine on cholesterol, fibrinogen and C-reactive protein. Toxicol Rev. 2006;25(1):55-69. [PubMed:16856769 ]
  11. Lamarine RJ: Selected health and behavioral effects related to the use of caffeine. J Community Health. 1994 Dec;19(6):449-66. [PubMed:7844249 ]
  12. James JE: Critical review of dietary caffeine and blood pressure: a relationship that should be taken more seriously. Psychosom Med. 2004 Jan-Feb;66(1):63-71. [PubMed:14747639 ]
  13. Higdon JV, Frei B: Coffee and health: a review of recent human research. Crit Rev Food Sci Nutr. 2006;46(2):101-23. [PubMed:16507475 ]
  14. Nehlig A, Daval JL, Debry G: Caffeine and the central nervous system: mechanisms of action, biochemical, metabolic and psychostimulant effects. Brain Res Brain Res Rev. 1992 May-Aug;17(2):139-70. [PubMed:1356551 ]
  15. Benjamin LT Jr, Rogers AM, Rosenbaum A: Coca-Cola, caffeine, and mental deficiency: Harry Hollingworth and the Chattanooga trial of 1911. J Hist Behav Sci. 1991 Jan;27(1):42-55. [PubMed:2010614 ]
  16. Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. [PubMed:6207592 ]
  17. Smit HJ, Gaffan EA, Rogers PJ: Methylxanthines are the psycho-pharmacologically active constituents of chocolate. Psychopharmacology (Berl). 2004 Nov;176(3-4):412-9. Epub 2004 May 5. [PubMed:15549276 ]
  18. Haskell CF, Kennedy DO, Wesnes KA, Milne AL, Scholey AB: A double-blind, placebo-controlled, multi-dose evaluation of the acute behavioural effects of guarana in humans. J Psychopharmacol. 2007 Jan;21(1):65-70. Epub 2006 Mar 13. [PubMed:16533867 ]