Theobromine
From Wikipedia, the free encyclopedia
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| Theobromine
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| Systematic (IUPAC) name | |
| 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione | |
| Identifiers | |
| CAS number | 83-67-0 |
| ATC code | C03BD01 R03DA07 |
| PubChem | 5429 |
| Chemical data | |
| Formula | C7H8N4O2 |
| Mol. weight | 180.166 |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status |
Uncontrolled substance |
| Routes | ? |
Theobromine is a bitter alkaloid of the methylxanthine family, which also includes the similar compounds theophylline and caffeine. Despite its name, the compound contains no bromine — theobromine is derived from Theobroma, the genus of the cacao tree, which is composed of the Greek roots theo ("God") and broma ("food"), meaning "food of the gods", with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds.
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[edit] Natural sources and effects in other animals
It is the primary alkaloid found in cocoa and chocolate, and is one of the causes for chocolate's mood-elevating effects. Theobromine is found in much larger quantities in dark chocolate (10 g/kg) as opposed to milk chocolate (1-5 g/kg). The amount found in chocolate is small enough that chocolate can be safely consumed by humans in large quantities, but animals that metabolize theobromine more slowly, such as cats and dogs, can easily consume enough chocolate to cause theobromine poisoning.
[edit] Effects on humans
Theobromine is a stimulant frequently confused with caffeine. Theobromine has very different effects on the human body from caffeine; it is a mild, lasting stimulant with a mood improving effect, whereas caffeine has a strong, immediate effect and increases awareness.
In medicine, it is used as a diuretic, vasodilator, and myocardial stimulant. There is a possible association between theobromine and an increased risk of suffering from prostate cancer.<ref>Slattery M, West D (1993). "Smoking, alcohol, coffee, tea, caffeine, and theobromine: risk of prostate cancer in Utah (United States).". Cancer Causes Control 4 (6): 559-63. PMID 8280834.</ref>
[edit] Additional uses
Scientists have recently discovered that theobromine has an antitussive effect superior to codeine by suppressing vagus nerve activity.<ref>Usmani O, Belvisi M, Patel H, Crispino N, Birrell M, Korbonits M, Korbonits D, Barnes P (2005). "Theobromine inhibits sensory nerve activation and cough.". FASEB J 19 (2): 231-3. PMID 15548587.</ref>
Theobromine is known to induce gene mutations in lower eukaryotes and bacteria. At the time of a 1997 report by the IARC, mutations had not been found in higher eukaryotes, such as humans.<ref>International Agency for Research on Cancer (November 17, 1991). Volume 51: Coffee, Tea, Mate, Methylxanthines and Methylglyoxal - Theobromine (PDF). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. WHO. Retrieved on 2006-09-19.</ref> Theobromine is used as an experimental teratogen in mice and rabbits.<ref>Rambali B, Andel I van, Schenk E, Wolterink G, Werken G van de, Stevenson H, Vleeming W (2002). "[The contribution of cocoa additive to cigarette smoking addiction]" (PDF). RIVM (report 650270002/2002).- The National Institute for Public Health and the Environment (Netherlands)</ref>
Theobromine is a contributing factor in acid reflux because it relaxes the esophageal sphincter muscle, allowing stomach acid access to the esophagus.
[edit] Other names
Other names include Riddospas, Riddovydrin, Santheose, Seominal, Theobrominum, Theoguardenal, Theominal and Théoxalvose.
[edit] Footnotes
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[edit] External links
| Antihypertensives (C02) and diuretics (C03) edit | ||
|---|---|---|
| Antiadrenergic agents (including alpha): |
Clonidine, Doxazosin, Guanethidine, Guanfacine, Lofexidine, Mecamylamine, Methyldopa, Moxonidine, Prazosin, Rescinnamine, Reserpine | |
| Vasodilators: |
Diazoxide, Hydralazine, Minoxidil, Nitroprusside, Phentolamine | |
| Other antihypertensives: | ||
| Low ceiling diuretics: |
Bendroflumethiazide, Chlorothiazide, Chlortalidone, Hydrochlorothiazide, Indapamide, Quinethazone, Mersalyl, Metolazone, Theobromine | |
| High ceiling diuretics: | ||
| Potassium-sparing diuretics: | ||
| Medications commonly used in asthma and COPD (primarily R03) edit | ||
|---|---|---|
| Anticholinergics: | ||
| Short acting β2-agonists: | ||
| Long acting β2-agonists (LABA): | Clenbuterol, Formoterol, Salmeterol | |
| Corticosteroids: | ||
| Leukotriene antagonists: | ||
| Xanthines: |
Aminophylline, Theobromine, Theophylline | |
| Mast cell stabilizers: | ||
| Combination products: |
Budesonide/formoterol, Fluticasone/salmeterol, Ipratropium/salbutamol | |
da:Theobromin de:Theobromin es:Teobromina fr:Théobromine it:Teobromina nl:Theobromine no:Teobromin nn:Teobromin pl:Teobromina pt:Teobromina ru:Теобромин sk:Teobromín sv:Teobromin uk:Теобромін
