Caffeine

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Caffeine molecular structure

Caffeine is an alkaloid found naturally in such foods as coffee beans, tea, kola nuts, Yerba maté, guarana, and (in small amounts) cacao beans. It is added to some soft drinks such as colas, Irn-Bru and Mountain Dew.

Caffeine has a characteristic intensely bitter taste. Its main pharmacological properties are: a stimulant action on the central nervous system with psychotropic effects and stimulation of respiration, a stimulation of the heart rate, and a diuretic effect. Caffeine consumption leads to pharmacologic tolerance with defined withdrawal symptoms.

Chemical properties

Caffeine is an alkaloid of the methylxanthine family, which also includes the similar compounds theophylline and theobromine. In its pure state it is an intensely bitter white powder. Its chemical formula is C₈H₁₀N₄O₂, its systematic name is 1,3,7-trimethylxanthine or 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione, and its structure is shown above.

Physical properties

Pure caffeine occurs as odorless, white, fleecy masses, glistening needles or powder.

Boiling point: 178 °C (sublimes)
Melting point: 238 °C
Specific gravity: 1.2    
Volatility: 0.5%
Vapor pressure: 760 mm Hg @ 178 °C
pH: 6.9 (1% solution)
Solubility in water: 2.17%    
Vapor density: 6.7
Molecular weight: 194.19

Sources

The main source of caffeine in food industry is the coffee bean. The caffeine content can vary significantly. In 2004 some trees were found in Ethiopia that contain one-fifteenth the caffeine of average plants. Beans from such trees may be used in the future to produce better quality decaffeinated coffee.

One dose of caffeine is generally considered to be 100 mg, delivered by one 5 fl oz / 150 ml cup of drip coffee or one (or one-half) caffeine tablet. Real-world coffee varies considerably in caffeine content per cup, from about 75 to 250 mg. Black tea contains somewhat less caffeine per serving than coffee, depending on the strength of the brew, and green tea contains significantly less. Colas also typically contain less than coffee, but some "energy" colas and similar drinks can have considerably more (the caffeine strength of soft drinks being controlled entirely by the manufacturer, with high caffeine content a popular marketing feature).

The amount of caffeine in some common consumables is approximately as follows:

Chocolate

• Chocolate, bittersweet - 25 mg/oz (875 mg/kg)
• Chocolate, milk - 3 to 6 mg/oz (100 to 210 mg/kg)
• Cocoa - 0.5 mg/floz (17 mg/litre)

Coffee

• Coffee, brewed (drip) - 4 to 20 mg/floz (130 to 680 mg/litre) (40 to 170 mg per 5 fl oz cup)
• Coffee, decaffeinated - 0.4 to 0.6 mg/floz (13 to 20 mg/litre)
• Coffee, instant - 4 to 12 mg/floz (130 to 400 mg/litre)
• Espresso - 100 mg/floz (3400 mg/litre)

Teas and other infusions

• Black tea, brewed (USA) - 2.5 to 11 mg/floz (85 to 370 mg per litre)
• Black tea, brewed (other) - 3 to 14 mg/floz (100 to 470 mg/litre)
• Black tea, canned iced - 2 to 3 mg/floz (70 to 100 mg/litre)
• Black tea, instant - 3.5 mg/floz (120 mg/litre)
• Oolong, 3.75 mg/floz (120 mg per litre) (12 to 55 mg per tea bag, i.e. one serving)
• Green tea, 2.5 mg/floz (85 mg/litre) (8 to 30 mg per tea bag, i.e. one serving)
• White tea, 2.0 mg/floz (68 mg/litre) (6 to 25 mg per tea bag, i.e. one serving)
• Decaf, 0.5 mg/oz (17 mg/litre) (1 to 4 mg per tea bag, i.e. one serving)

Caffeine is sometimes called theine when it is found in tea, as the caffeine in tea was once thought to be a separate compound to the caffeine found in coffee. The mateine described in some literature as the primary psychoactive constituent of yerba mate is also generally considered to be identical to caffeine.

• Tisanes (i.e. Herbal teas) - caffeine content depends on the herb, e.g. Chamomile and Rooibos "teas" have no caffeine while Yerba maté and Guarana do contain varying quantities. Many tea drinkers characterise herbal tea simply as that which, unlike black or green tea, contains no caffeine.

Other sources

• Energy drink - 10 mg/floz (340 mg/litre). Some countries limit the caffeine content at 135 mg/litre.
• Soft drink (caffeinated) - 3 to 8 mg/floz (100 to 270 mg/litre)
• Pill (caffeine) - 200 mg (100 mg in many countries within EU)

Equivalents 200 mg of Caffeine

• One caffeine pill (Two in some countries where these are 100 mg)
• One shot of espresso (2 oz)
• ~2 cups (5 floz) of regular coffee
• ~1.3 L soft drink (these can vary widely in content)
• ~1 kg (~2 lb) of milk chocolate or ~0.25 kg of bittersweet chocolate (~0.5 lb)
• ~5 cups (8 floz) of black tea or ~10 cups (8 oz) of green tea

In the European Union, a warning must be placed on packaging if the caffeine content of any beverage exceeds 150 mg per litre. This includes caffeine from any source (including guarana, which is often found in energy drinks). In many countries, caffeine is classified as a flavouring.

Metabolism and toxicology

Caffeine is thought to act on the brain by blocking adenosine receptors. Adenosine, when bound to receptors of nerve cells, slows down nerve cell activity; this happens, among other times, during sleep. The caffeine molecule, being similar to adenosine, binds to the same receptors but doesn't cause the cells to slow down; instead, the caffeine blocks the receptors and thereby the adenosine action. The resulting increased nerve activity causes the release of the hormone epinephrine, which in turn leads to several effects such as higher heart rate, increased blood pressure, increased blood flow to muscles, decreased blood flow to the skin and inner organs, and release of glucose by the liver. In addition, caffeine, similar to amphetamines, increases the levels of the neurotransmitter dopamine in the brain.

Caffeine is quickly and completely removed from the brain and, unlike other CNS stimulants or alcohol, its effects are short lived. In many people, caffeine does not negatively affect concentration or higher mental functions, and hence caffeinated drinks are often consumed in the course of work.

Continued consumption of caffeine can lead to tolerance. Upon withdrawal, the body becomes oversensitive to adenosine, causing the blood pressure to drop dramatically, leading to headache and other symptoms. Recent studies suggest that caffeine intake (in coffee) may decrease the risk of developing Parkinson's disease, but additional study is needed.

Too much caffeine can lead to caffeine intoxication. The symptoms of this disorder are restlessness, nervousness, excitement, insomnia, flushed face, diuresis, and gastrointestinal complaints. They can occur in some people after as little as 250 mg per day. More than 1 g per day may result in muscle twitching, rambling flow of thought and speech, cardiac arrhythmia or tachycardia, and psychomotor agitation. Caffeine intoxication can lead to symptoms similar to panic disorder and generalized anxiety disorder. The LD₅₀ is estimated to be about 192 mg/kg of body mass, or about 72 cups of coffee for an average adult, while the half life ranges from 3.5 to 100 hours. In adults the half life is generally around 5 hours. However contraceptive pills increase this to around 12 hours and for women over 3 months pregnant it varies from 10 to 18 hours.

While safe for humans, caffeine and its related compounds theobromine and theophylline are considerably more toxic to some other animals such as dogs and horses, due to differences in liver metabolism.

A fascinating recent finding is that intake of caffeine can up to halve a patient's risk of diabetes mellitus type 2. While this was originally noticed in patients who consumed high amounts (7 cups a day), the relationship has now been shown to be linear (Salazar-Martinez 2004).

Abuse and addiction

Caffeine, in its many forms, has been used for its stimulating effects. In modern times, though, the substance can be produced in much higher quantities, and has found its way into many products. Purer forms, such as those in caffeine pills, are available easily. These pills are often used by college students and graveyard shift workers to last an entire night with no sleep.

Caffeine pills have been under media fire for recent and past deaths of students, usually take on the form of a caffeine overdose. One such example of this was the death of North Carolina student, Jason Allen. He swallowed most of a bottle of 90 such pills, which is the equivalent of 250 cups of coffee (or, alternatively, a gallon and a half (5L) of espresso, or 22 gallons (~150 L) of Mountain Dew, which is not caffeinated in Canada for legal reasons). This was probably 18 grams (not milligrams) of caffeine, since caffeine pills are restricted to 200 milligrams or less in the U.S., and most pep pill manufacturers make them in that size. A few other deaths by caffeine overdose have been known, almost always in the case of massive pill consumption on dares.

One dangerous form of caffeine use is to stay alert when one is under the influence of alcohol or in severe sleep debt. This tricks users into thinking they are more alert than they really are. Taking part in certain activities, such as driving may be dangerous in such cases.

History

Caffeine was isolated by the German chemist Friedrich Ferdinand Runge in 1819. According to the legend, he did this at the instigation of Johann Wolfgang von Goethe (Weinberg & Bealer 2001).

References

• Salazar-Martinez E, Willet WC, Ascherio A, Manson JE, Leitzmann MF, Stampfer MJ, Hu FB. Coffee consumption and risk for type 2 diabetes mellitus. Ann Intern Med 2004;140:1-8.
• Weinberg BA, Bealer BK. The world of caffeine. New York & London: Routledge, 2001. ISBN 0-415-92722-6.
• Kruszelnicki. Munching Maggots, Noah's Ark and TV Heart Attacks. HarperCollinsPublishers, 1998. ISBN 0-7322-5858-8.

External links

• Caffeine Content in Beverages
• Caffeine Content of Foods
• Caffeine Intoxication
• Caffeine Intoxication
• Caffeine Health
• Description of the Yerba Mate
• Is Caffeine a Health Hazard?
• Why do plants make caffeine ?
• The Caffeine Faq

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