Record Information |
---|
Version | 1.0 |
---|
Created at | 2006-02-16 08:53:46 UTC |
---|
Updated at | 2020-11-24 22:12:05 UTC |
---|
NP-MRD ID | NP0000009 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Caffeine |
---|
Description | Caffeine, 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 | |
---|
Synonyms | Value | Source |
---|
1,3,7-Trimethyl-2,6-dioxopurine | ChEBI | 1,3,7-Trimethylpurine-2,6-dione | ChEBI | 1,3,7-Trimethylxanthine | ChEBI | 1-Methyltheobromine | ChEBI | 3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion | ChEBI | 7-Methyltheophylline | ChEBI | Anhydrous caffeine | ChEBI | Cafeina | ChEBI | Cafeine | ChEBI | Coffein | ChEBI | Guaranine | ChEBI | Koffein | ChEBI | Mateina | ChEBI | Methyltheobromine | ChEBI | Teina | ChEBI | Thein | ChEBI | Theine | ChEBI | Respia | Kegg | 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione | HMDB | 1-Methyl-theobromine | HMDB | 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione | HMDB | 7-Methyl theophylline | HMDB | Anhydrous caffeine (JP15) | HMDB | Hycomine | HMDB | Lanorinal | HMDB | Methyltheobromide | HMDB | Methylxanthine theophylline | HMDB | Monohydrate caffeine | HMDB | Propoxyphene | HMDB | Merck dura brand OF caffeine | HMDB | Thompson brand 1 OF caffeine | HMDB | Bristol-myers squibb brand OF caffeine | HMDB | Caffedrine | HMDB | Dexitac | HMDB | Percoffedrinol N | HMDB | Pierre fabre brand OF caffeine | HMDB | Republic drug brand OF caffeine | HMDB | Thompson brand 2 OF caffeine | HMDB | Vivarin | HMDB | Coffeinum N | HMDB | Coffeinum purrum | HMDB | Durvitan | HMDB | GlaxoSmithKline brand OF caffeine | HMDB | No doz | HMDB | Percutaféine | HMDB | Quick-pep | HMDB | Seid brand OF caffeine | HMDB | Berlin-chemie brand OF caffeine | HMDB | Passauer brand OF caffeine | HMDB | Quick pep | HMDB | QuickPep | HMDB |
|
---|
Chemical Formula | C8H10N4O2 |
---|
Average Molecular Weight | 194.1906 |
---|
Monoisotopic Molecular Weight | 194.080375584 |
---|
IUPAC Name | 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione |
---|
Traditional Name | caffeine |
---|
CAS Registry Number | 58-08-2 |
---|
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 Key | RYYVLZVUVIJVGH-UHFFFAOYSA-N |
---|
Spectra |
---|
|
| | Species of Origin |
---|
Species | Animalia |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Imidazopyrimidines |
---|
Sub Class | Purines and purine derivatives |
---|
Direct Parent | Xanthines |
---|
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 Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | 238 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 21.6 mg/mL at 25 °C | Not Available | LogP | -0.07 | HANSCH,C ET AL. (1995) |
|
---|
Predicted Properties | |
---|
General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Septer S, Thompson ES, Willemsen-Dunlap A: Anesthesia concerns for children with tuberous sclerosis. AANA J. 2006 Jun;74(3):219-25. [PubMed:16786916 ]
- 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 ]
- 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 ]
- Lamarine RJ: Selected health and behavioral effects related to the use of caffeine. J Community Health. 1994 Dec;19(6):449-66. [PubMed:7844249 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. [PubMed:6207592 ]
- 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 ]
- 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 ]
|
---|