Caffeine (/kfin, kfin, kfin/) is a central nervous system (CNS) stimulant of

the methylxanthine class of psychoactive drugs.[9] It is the world's most widely

consumed psychoactive drug, but unlike many other psychoactive substances, it is legal and
unregulated in nearly all parts of the world. It is a bitter, white crystalline purine,
a methylxanthine alkaloid, and thus closely related chemically to the adenine and guanine contained
in deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, nuts, or leaves
of a number of plants native to South America and East Asia. The most well known source of
caffeine is the seed (commonly incorrectly referred to as the "bean") of Coffea plants. Beverages
containing caffeine are ingested to relieve or prevent drowsiness and to increase one's energy level.
Caffeine is extracted from the plant part containing it for making beverages bysteeping it in water, a
process called infusion. These beverages are very popular; in North America, 90% of adults
consume caffeine daily.[10]
Caffeine is classified by the Food and Drug Administration as "generally recognized as safe"
(GRAS). Toxic doses, over 10 grams per day for an adult, are much higher than typical dose of
under 500 milligrams per day. A cup of coffee contains 80175 mg of caffeine, depending on what
"bean" (seed) is used and how it is prepared (e.g. drip, percolation, or espresso). Thus it requires
roughly 50100 ordinary cups of coffee to reach a lethal dose. However pure powdered caffeine,
which is widely available as a dietary supplement, can be lethal in tablespoon-sized amounts. There
are several known mechanisms of action to explain the effects of caffeine. The most prominent is to
reversibly block the action of adenosine on its receptor, which blocks the onset of drowsiness
induced by adenosine. Caffeine also stimulates selected portions of the autonomic nervous system.
Caffeine can have both positive and negative health effects. It can be used to
treat bronchopulmonary dysplasia of prematurity, and to prevent apnea of prematurity: caffeine
citrate was placed on the WHO Model List of Essential Medicines in 2007.[11] It may confer a modest
protective effect against some diseases,[12] including Parkinson's disease[13] and certain types of
cancer. One meta-analysis concluded that cardiovascular disease such as coronary artery disease
and stroke is less likely with 35 cups of non-decaffeinated coffee per day but more likely with over 5
cups per day.[14] Some people experience insomnia or sleep disruption if they consume caffeine,
especially during the evening hours, but others show little disturbance. Evidence of a risk during
pregnancy is equivocal; some authorities recommend that pregnant women limit consumption to the
equivalent of two cups of coffee per day or less.[15][16] Whether or not caffeine is an addictive
drug depends on how an addiction is defined. It can produce a mild form of drug dependence
associated with withdrawal symptoms such as sleepiness, headache, and irritability when an
individual stops using caffeine after repeated daily intake. [2][4][17] Tolerance to the autonomic effects of
increased blood pressure and heart rate, and increased urine output, develops with chronic use (i.e.,
these symptoms become less pronounced or do not occur following consistent use). [citation needed]

Caffeine confers a survival advantage on the plant containing it in three ways. First, if it is ingested
by an insect feeding on and potentially damaging or killing the plant, caffeine functions as a natural
pesticide which can paralyze and kill the insect. Second, droppings from the plant infuse the
surrounding soil with caffeine, which can inhibit the growth of and kill competing seedlings (and
potentially its own progeny and itself). Third, caffeine can enhance the reward memory of pollinators
such as honey bees, thus increasing the numbers of its progeny.
Contents
[hide]

1 Uses
o

1.1 Medical

1.2 Enhancing performance

2 Side effects
o

2.1 Pregnancy risk

2.2 Reinforcement disorders

2.3 Risk of other diseases

3 Overdose

4 Pharmacology
o

4.1 Pharmacodynamics

4.2 Pharmacokinetics

5 Physical and chemical properties

o

5.1 Biosynthesis

5.2 Detection in body fluids

5.3 Analogs
6 Natural occurrence

7 Products
o

7.1 Beverages

7.2 Chocolate

7.3 Tablets

7.4 Other oral products

7.5 Inhalants

7.6 Combinations with other drugs

8 Decaffeination

9 History
o

9.1 Discovery and spread of use

9.2 Chemical identification, isolation, and synthesis

10 Society and culture

o

10.1 Consumption

10.2 Governments

10.3 Religions

11 Other organisms

12 References

13 Bibliography

14 External links

Uses
Main article: Health effects of caffeine

Medical

Caffeine is used in

bronchopulmonary dysplasia in premature infants for both prevention[18] and treatment.[19] It

may improve weight gain during therapy[20] and reduce the incidence of cerebral palsy as well as
reduce language and cognitive delay.[21][22] On the other hand, subtle long-term side effects are
possible.[23]

apnea of prematurity as a primary treatment,[24] but not prevention.[25][26]

orthostatic hypotension treatment.[26][27]

Enhancing performance

Health effects of caffeine

Caffeine is a central nervous system and metabolic stimulant,[9] and is used to reduce
physical fatigue and to prevent or treatdrowsiness. It produces increased wakefulness, faster and
clearer flow of thought, increased focus, and better general body coordination. [28] The amount of
caffeine needed to produce these effects varies from person to person, depending on body size and
degree of tolerance. Desired effects begin less than an hour after consumption, and a moderate
dose usually subsides in about five hours.[28]
Caffeine has the desired effect of delaying/preventing sleep, but does not affect all people in the
same way. It also improves performance during sleep deprivation. [29] In shift workers it leads to fewer
mistakes caused by drowsiness.[30]
In athletes, moderate doses of caffeine can improve sprint,[31] endurance,[32] and team sports
performance,[33] but the improvements are usually not substantial. Some evidence suggests that
coffee does not produce the performance enhancing effects observed in other caffeine sources. [34]

Side effects

Minor undesired symptoms from caffeine ingestion not sufficiently severe to warrant a psychiatric
diagnosis are common, and include mild anxiety, jitteriness, insomnia, and interference with coordination in athletes.[35] The caffeine-induced disorders recognized in the The Diagnostic and
Statistical Manual of Mental Disorders, Fifth Edition (DSM-5) are: caffeine-induced anxiety
disorder, caffeine-induced sleep disorder, caffeine intoxication, caffeine withdrawal and caffeinerelated disorder not otherwise specified.[36] Caffeine in low doses may cause weak bronchodilation for
up to four hours in asthmatics: it should therefore be avoided prior to having any lung function test
performed.[37]
Caffeine can have negative effects on anxiety disorders.[38] A number of clinical studies have shown a
positive association between caffeine and anxiogenic effects and/or panic disorder.[39][40] At high
doses, typically greater than 300 mg, caffeine can both cause and worsen anxiety[41] or, rarely,
trigger mania or psychosis. In moderate doses, caffeine may reduce symptoms of depression and
lower suicide risk.[42] For some people, discontinuing caffeine use can significantly reduce anxiety.[43]
Caffeine has mild cognition enhancing properties which are related to its effect on wakefulness,
concentration, and mood.[44] At normal doses, caffeine improves memory in sleep deprived subjects
and facilitates passive learning, but has both beneficial and harmful effects on working
memory depending on the nature of the task.[44] Concurrent caffeine andL-theanine use has
synergistic psychoactive effects that promote alertness, attention, and task switching;[45] these effects
are most pronounced during the first hour post-dose. [45]
Caffeine increases urine output acutely, but not chronically. When doses of caffeine equivalent to 2
3 cups of coffee are administered to people who have not consumed caffeine during prior days, it
results in a mild increase in urinary output.[46] This increase is due to both a diuresis (increase in
water excretion) and a natriuresis (increase in saline excretion); and is mediated via proximal tubular
adenosine receptor blockade.[47] Because of this effect, some authorities have recommended that
athletes and airline passengers avoid caffeine to reduce the risk of dehydration, i.e. hypernatremia,
and the risk of extracellular fluid volume depletion. However, chronic users of caffeine develop
a tolerance to these effects, and have no chronic increase in urinary output.[48][49]

Pregnancy risk
Caffeine consumption during pregnancy does not appear to increase the risk of congenital
malformations, miscarriage or growth retardation even when consumed in moderate to high
amounts.[50] However, as the data supporting this conclusion is of poor quality, some suggest limiting
caffeine consumption during pregnancy.[51][52] The UK Food Standards Agency has recommended that
pregnant women should limit their caffeine intake, out of prudence, to less than 200 mg of caffeine a
day the equivalent of two cups of instant coffee, or one and a half to two cups of fresh coffee.
[53]

The American Congress of Obstetricians and Gynecologists (ACOG) concluded in 2010 that

caffeine consumption is safe up to 200 mg per day in pregnant women.[16] Although the evidence that

caffeine may be harmful during pregnancy is equivocal, there is some evidence that the hormonal
changes during pregnancy slow the metabolic clearance of caffeine from the system, causing a
given dose to have longer-lasting effects (as long as 15 hours in the third trimester).[54]

Reinforcement disorders
Addiction
Whether or not caffeine can result in an addictive disorder depends on how addiction is defined.
Some diagnostic models, such as the ICDM-9 and ICD-10, include a classification of caffeine
addiction under a broader diagnostic model.[55] Some state that certain users can become addicted
and therefore unable to decrease use even though they know there are negative health effects. [56][57]
Some state that research does not provide support for an underlying biochemical mechanism for
caffeine addiction.[2][58][59][60] Other research states it can affect the reward system.[61]
"Caffeine addiction" was added to the ICDM-9 and ICD-10; however, its addition was contested with
claims that this diagnostic model of caffeine addiction is not supported by evidence. [2][3]
[62]

The American Psychiatric Association's DSM-5 does not include the diagnosis of a caffeine

addiction but propose criteria for the disorder for more study.[63][64]
Dependence and withdrawal
Mild physical dependence or psychological dependence may occur with repeated daily intake;[2] the
associated physical or psychological withdrawal state may involve symptoms such as fatigue,
headache, irritability, inability to concentrate, sleepiness or drowsiness, stomach pain, and joint pain.
[2][17]

Withdrawal headaches are experienced by roughly half of those who stop consuming caffeine for

two days following an average daily intake of 235 mg.[65]

The ICD-10 includes a diagnostic model for caffeine dependence, but the DSM-5 does not.[4]
[62]

The APA, which published the DSM-5, acknowledged that there was sufficient evidence in order to

create a diagnostic model of caffeine dependence for the DSM-5, but they noted that the clinical
significance of this disorder is unclear.[4] The DSM-5 instead lists "caffeine use disorder" in
the emerging models section of the manual.[4]
Tolerance
Tolerance to the desired effect of alertness does not occur following repeated use. Tolerance to
some undesired effects, particularly to caffeine's autonomic effects, develops quickly, especially
among heavy coffee and energy drink consumers.[66] Some coffee drinkers develop tolerance to its
undesired sleep-disrupting effects, but others apparently do not.[54]

Risk of other diseases

Coffee consumption is associated with a lower overall risk of cancer.[67] This is primarily due to a
decrease in the risks of hepatocellular and endometrial cancer, but it may also have a modest effect

on colorectal cancer.[68] There does not appear to be a significant protective effect against other types
of cancers, and heavy coffee consumption may increase the risk of bladder cancer.[68] A protective
effect of caffeine against Alzheimer's disease is possible, but the evidence is inconclusive.[69][70]
[71]

Moderate coffee consumption may decrease the risk of cardiovascular disease,[14] and it may

somewhat reduce the risk of type 2 diabetes.[72] Drinking four or more cups of coffee per day does not
affect the risk of hypertension compared to drinking little or no coffee. However those who drink 13
cups per day may be at a slightly increased risk.[73] Caffeine increasesintraocular pressure in those
with glaucoma but does not appear to affect normal individuals.[74] It may protect people from liver
cirrhosis.[75] There is no evidence that coffee stunts a child's growth. [76] Caffeine may increase the
effectiveness of some medications including ones used to treat headaches.[77] Caffeine may lessen
the severity of acute mountain sickness if taken a few hours prior to attaining a high altitude. [78]

Overdose

Primary symptoms of caffeine intoxication[79]

Consumption of 10001500 mg per day is associated with a condition known as caffeinism.

[80]

Caffeinism usually combines caffeinedependency with a wide range of unpleasant symptoms

including nervousness, irritability, restlessness, insomnia, headaches, and palpitations after caffeine
use.[81]
Caffeine overdose can result in a state of central nervous system over-stimulation called caffeine
intoxication (DSM-IV 305.90).[82] This syndrome typically occurs only after ingestion of large amounts
of caffeine, well over the amounts found in typical caffeinated beverages and caffeine tablets (e.g.,
more than 400500 mg at a time). The symptoms of caffeine intoxication are comparable to the
symptoms of overdoses of other stimulants: they may include restlessness, fidgeting, anxiety,
excitement, insomnia, flushing of the face, increased urination, gastrointestinal disturbance, muscle
twitching, a rambling flow of thought and speech, irritability, irregular or rapid heart beat,
and psychomotor agitation.[79] In cases of much larger overdoses, mania, depression, lapses in

judgment, disorientation, disinhibition, delusions, hallucinations, or psychosis may occur,

and rhabdomyolysis (breakdown of skeletal muscle tissue) can be provoked.[83][84]
Massive overdose can result in death.[85][86] The LD50 of caffeine in humans is dependent on individual
sensitivity, but is estimated to be 150 to 200 milligrams per kilogram of body mass (75100 cups of
coffee for a 70 kilogram adult).[87] A number of fatalities have been caused by overdoses of readily
available powdered caffeine supplements, for which the estimated lethal amount is less than a
tablespoon.[88] The lethal dose is lower in individuals whose ability to metabolize caffeine is impaired
due to genetics or chronic liver disease[89] A death was reported in a man with liver cirrhosis who
overdosed on caffeinated mints.[90][91][92]
Treatment of mild caffeine intoxication is directed toward symptom relief; severe intoxication may
require peritoneal dialysis, hemodialysis, or hemofiltration.[79]

Pharmacology
Pharmacodynamics
Structure of a typical chemical synapse

Postsynaptic
density
Voltagegated Ca++
channel
Synaptic
vesicle
Neurotransmitter

transporter
Receptor
Neurotransmitter
Axon terminal
Synaptic cleft
Dendrite

Caffeine's primary mechanism of action is as an antagonist of adenosine receptors in the brain

In the absence of caffeine and when a person is awake and alert, little adenosine is present in (CNS)
neurons. With a continued wakeful state, over time it accumulates in the neuronal synapse, in turn
binding to and activating adenosine receptors found on certain CNS neurons; when activated, these
receptors produce a cellular response that ultimately increases drowsiness. When caffeine is
consumed, it antagonizes adenosine receptors; in other words, caffeine prevents adenosine from
activating the receptor by blocking the location on the receptor where adenosine binds to it. As a
result, caffeine temporarily prevents or relieves drowsiness, and thus maintains or restores
alertness.[5]
Receptor and ion channel targets
Caffeine is a receptor antagonist at all adenosine receptor subtypes (A1, A2A, A2B,
and A3 receptors).[5]Antagonism at these receptors stimulates the medullary vagal, vasomotor,
and respiratory centers, which increases respiratory rate, reduces heartrate, and constricts blood
vessels.[5] Adenosine receptor antagonism also promotes neurotransmitter release
(e.g., monoamines and acetylcholine), which endows caffeine with its stimulant effects;[5]
[93]

adenosine acts as an inhibitory neurotransmitter that suppresses activity in the central nervous

system. Increased heart rate is caused by blockade of the adenosine A1 receptor.[5]

Because caffeine is both water- and lipid-soluble, it readily crosses the bloodbrain barrier that
separates the bloodstream from the interior of the brain. Once in the brain, the principal mode of
action is as a nonselective antagonist of adenosine receptors (in other words, an agent that reduces
the effects of adenosine). The caffeine molecule is structurally similar to adenosine, and is capable

of binding to adenosine receptors on the surface of cells without activating them, thereby acting as
a competitive inhibitor.[94]
In addition to its activity at adenosine receptors, caffeine is an inositol triphosphate receptor
1 antagonist and a voltage-independent activator of the ryanodine receptors (RYR1, RYR2,
and RYR3).[95] It is also a competitive antagonist of the ionotropic glycine receptor.[96]
Enzyme targets
Caffeine, like other xanthines, also acts as a phosphodiesterase inhibitor.[97] As a competitive
nonselective phosphodiesterase inhibitor,[98] caffeine raises intracellular cAMP, activates protein
kinase A, inhibits TNF-alpha[99][100] and leukotriene[101] synthesis, and reduces inflammation and innate
immunity.[101] Caffeine is also significantly implicated incholinergic system where it e.g. inhibits
enzyme acetylcholinesterase.[102]
Off-target effects
Caffeine antagonizes adenosine A2A receptors in the ventrolateral preoptic area (VLPO), thereby
inducing inhibitory GABA neurotransmission to the tuberomammillary nucleus,
ahistaminergic projection nucleus that activation-dependently promotes sleep. [103] Inhibition of the
tuberomammillary nucleus is the chief mechanism by which caffeine produces wakefulnesspromoting effects.[103]

Pharmacokinetics

Caffeine is metabolized in the liver into three primary metabolites: paraxanthine(84%), theobromine (12%),
and theophylline(4%)

Caffeine from coffee or other beverages is absorbed by the small intestine within 45 minutes of
ingestion and distributed throughout all bodily tissues.[6] Peak blood concentration is reached within
12 hours.[citation needed] It is eliminated by first-order kinetics.[104]Caffeine can also be absorbed rectally,
evidenced by suppositories of ergotamine tartrate and caffeine (for the relief of migraine)
[105]

and chlorobutanol and caffeine (for the treatment of hyperemesis).[106]

Caffeine's biological half-life the time required for the body to eliminate one-half of a dose varies
widely among individuals according to factors such as pregnancy, other drugs, liver enzyme function
level (needed for caffeine metabolism) and age. In healthy adults, caffeine's half-life is between 3
7 hours.[5] Nicotine decreases the half-life by 3050%,[54] while oral contraceptivescan double it[54] and
pregnancy can raise it to as much as 15 hours during the last trimester.[54] In newborns the half-life
can be 80 hours or more, dropping very rapidly with age, possibly to less than the adult value by age
6 months.[54] The antidepressantfluvoxamine (Luvox) reduces the clearance of caffeine by more than
90%, and increases its elimination half-life more than tenfold; from 4.9 hours to 56 hours.[107]
Caffeine is metabolized in the liver by the cytochrome P450 oxidase enzyme system, in particular, by
the CYP1A2 isozyme, into three dimethylxanthines,[108] each of which has its own effects on the body:

Paraxanthine (84%): Increases lipolysis, leading to elevated glycerol and free fatty
acid levels in blood plasma.

Theobromine (12%): Dilates blood vessels and increases urine volume. Theobromine is also
the principal alkaloid in the cocoa bean (chocolate).

Theophylline (4%): Relaxes smooth muscles of the bronchi, and is used to treat asthma.
The therapeutic dose of theophylline, however, is many times greater than the levels attained
from caffeine metabolism.[citation needed]

1,3,7-Trimethyluric acid is a minor caffeine metabolite.[5] Each of these metabolites is further

metabolized and then excreted in the urine. Caffeine can accumulate in individuals with severe liver
disease, increasing its half-life.[109]
A 2011 review found that increased caffeine intake was associated with a variation in two genes that
increase the rate of caffeine catabolism. Subjects who had this mutation on
both chromosomes consumed 40 mg more caffeine per day than others.[110] This is presumably due
to the need for a higher intake to achieve a comparable desired effect, not that the gene "forces"
people to drink coffee.

Physical and chemical properties

Pure anhydrous caffeine is a white odorless powder with a melting point of 235238 C.[7][8] Caffeine
is moderately soluble in water at room temperature (2 g/100 mL), but very soluble in boiling water
(66 g/100 mL).[111] It is also moderately soluble in ethanol (1.5 g/100 mL).[111] It is weakly basic (pKa =
~0.6) requiring strong acid to protonate it.[112]Caffeine does not contain any stereogenic centers[113] and
hence is classified as an achiral molecule.[114]
The xanthine core of caffeine contains two fused rings, a pyrimidinedione and imidazole. The
pyrimidinedione in turn contains two amide functional groups that exist predominately in

a zwitterionic resonance the location from which the nitrogen atoms are double bonded to their
adjacent amide carbons atoms. Hence all six of the atoms within the pyrimidinedione ring system are
sp2 hybridized and planar. Therefore, the fused 5,6 ring core of caffeine contains a total of ten pi
electrons and hence according to Hckel's rule is aromatic.[115]

Biosynthesis
Caffeine may be synthesized from dimethylurea and malonic acid,[116][117][118] but is rarely obtained from
synthesis since it is readily available as a byproduct of decaffeination. [119]

Caffeine biosynthesis[120]

Caffeine laboratory synthesis[116][117]

Detection in body fluids

Caffeine can be quantified in blood, plasma, or serum to monitor therapy in neonates, confirm a
diagnosis of poisoning, or facilitate a medicolegal death investigation. Plasma caffeine levels are
usually in the range of 210 mg/L in coffee drinkers, 1236 mg/L in neonates receiving treatment for
apnea, and 40400 mg/L in victims of acute overdosage. Urinary caffeine concentration is frequently
measured in competitive sports programs, for which a level in excess of 15 mg/L is usually
considered to represent abuse.[121]

Analogs
Some analog substances have been created which mimic caffeine's properties with either function or
structure or both, one of the latter is the drug DMPX.[122]

Natural occurrence

Around sixty plant species are known to contain caffeine. [123] Common sources are the "bean" (seed)
of the coffee plant (the quantity varies, but 1.3% is a typical value[124]); in the leaves of the tea bush;
and in kola nuts. Other sources include yaupon holly leaves, South American holly yerba
mate leaves, seeds from Amazonian maple guarana berries, and Amazonian holly guayusa leaves.
Temperate climates around the world have produced unrelated caffeine containing plants.
Caffeine in plants acts as a natural pesticide: it can paralyze and kill predator insects feeding on the
plant:[125] high caffeine levels are found in coffee seedlings when they are developing foliage and lack
mechanical protection.[126] In addition, high caffeine levels are found in the surrounding soil of coffee
seedlings, which inhibits seed germination of nearby coffee seedlings, thus giving seedlings with the
highest caffeine levels fewer competitors for existing resources for survival. [127]
The differing perceptions in the effects of ingesting beverages made from various plants containing
caffeine could be explained by the fact that these beverages also contain varying mixtures of
other methylxanthine alkaloids, including the cardiac stimulants theophylline and theobromine,
and polyphenols that can form insoluble complexes with caffeine.[128][clarification needed]

Products
See also: Caffeinated drink
Caffeine Content in Select Food and Drugs [129][130][131][132][133]

Product

Serving size

Caffein
e per
serving
(mg)

Caffeine
(mg/L)

Caffeine tablet
(regular-strength)

1 tablet

100

Caffeine tablet
(extra-strength)

1 tablet

200

Excedrin tablet

1 tablet

65

Hershey's Special
Dark (45% cacao
content)

1 bar (43 g or 1.5 oz)

31

Hershey's Milk
Chocolate (11%
cacao content)

1 bar (43 g or 1.5 oz)

10

Percolated coffee

207 mL (7.0 US fl oz)

80135

386652

Drip coffee

207 mL (7.0 US fl oz)

115175

555845

Coffee, decaffeinated

207 mL (7.0 US fl oz)

515

2472

Coffee, espresso

4460 mL (1.5

100

1,691

Caffeine Content in Select Food and Drugs [129][130][131][132][133]

Product

Serving size

Caffein
e per
serving
(mg)

2.0 US fl oz)

Caffeine
(mg/L)
2,254

Tea black, green,

and other types,
steeped for 3 min.

177 millilitres (6.0 US fl oz)

2274[132][133]

124418

Guayak yerba
mate(loose leaf)

6 g (0.21 oz)

85[134]

approx. 358

Coca-Cola Classic

355 mL (12.0 US fl oz)

34

96

Mountain Dew

355 mL (12.0 US fl oz)

54

154

Pepsi Max

355 mL (12.0 US fl oz)

69

194

Guaran Antarctica

350 mL (12 US fl oz)

30

100

Jolt Cola

695 mL (23.5 US fl oz)

280

403

Red Bull

250 mL (8.5 US fl oz)

80

320

Products containing caffeine are coffee, tea, soft drinks ("colas"), energy drinks, other
beverages,chocolate,[135] caffeine tablets, other oral products, and inhalation.

Beverages
Coffee
The world's primary source of caffeine is the coffee "bean" (which is the seed of the coffee plant),
from which coffee is brewed. Caffeine content in coffee varies widely depending on the type of coffee
bean and the method of preparation used;[136] even beans within a given bush can show variations in
concentration. In general, one serving of coffee ranges from 80 to 100 milligrams, for a single shot
(30 milliliters) of arabica-variety espresso, to approximately 100125 milligrams for a cup (120
milliliters) of drip coffee.[137][138] Arabica coffee typically contains half the caffeine of the robusta variety.
[136]

In general, dark-roast coffee has very slightly less caffeine than lighter roasts because the

roasting process reduces caffeine content of the bean by a small amount. [137][138]
Tea
Tea contains more caffeine than coffee by dry weight. A typical serving, however, contains much
less, since tea is normally brewed more weakly than coffee. Also contributing to caffeine content are
growing conditions, processing techniques, and other variables. Thus, certain types of tea may
contain somewhat more caffeine than other teas.[139]

Tea contains small amounts of theobromine and slightly higher levels of theophylline than coffee.
Preparation and many other factors have a significant impact on tea, and color is a very poor
indicator of caffeine content. Teas like the pale Japanese green tea, gyokuro, for example, contain
far more caffeine than much darker teas like lapsang souchong, which has very little.[139]
Soft drinks and energy drinks
Caffeine is also a common ingredient of soft drinks, such as cola, originally prepared from kola nuts.
Soft drinks typically contain 10 to 69 milligrams of caffeine per 12 ounce serving. [citation needed] By
contrast,energy drinks, such as Red Bull, can start at 80 milligrams of caffeine per serving. The
caffeine in these drinks either originates from the ingredients used or is an additive derived from the
product ofdecaffeination or from chemical synthesis. Guarana, a prime ingredient of energy drinks,
contains large amounts of caffeine with small amounts of theobromine and theophylline in a naturally
occurring slow-release excipient.[140]
Other beverages

Mate is a drink popular in many parts of South America. Its preparation consists of filling a
gourd with the leaves of the South American holly yerba mate, pouring hot but not boiling water
over the leaves, and drinking with a straw, the bombilla, which acts as a filter so as to draw only
the liquid and not the yerba leaves.[citation needed]

Guaran seeds ("beans") are used in making the commercially sold beverage Guaran
Antarctica, which originated in Brazil and is currently the fifteenth most popular soft drink in the
world.[citation needed]

The leaves of Ilex guayusa, the Equadorian holly tree, are placed in boiling water to make a
guayusa tea, which is both brewed locally and sold commercially throughout the world. [citation needed]

Chocolate
Chocolate derived from cocoa beans contains a small amount of caffeine. The weak stimulant effect
of chocolate may be due to a combination of theobromine and theophylline, as well as caffeine. [141] A
typical 28-gram serving of a milk chocolate bar has about as much caffeine as a cup of decaffeinated
coffee. By weight, dark chocolate has one to two times the amount caffeine as coffee: 80160 mg
per 100 g.[130]

Tablets

No-Doz 100 mg caffeine tablets

Tablets offer the advantages over coffee and tea of convenience, known dosage, and avoiding
concomitant fluid intake. Manufacturers of caffeine tablets claim that using caffeine of
pharmaceutical quality improves mental alertness.[citation needed] These tablets are commonly used by
students studying for their exams and by people who work or drive for long hours. [142]

Other oral products

One U.S. company is marketing oral dissolvable caffeine strips.[143] Another unusual intake route
is SpazzStick, a caffeinated lip balm.[144]Alert Energy Caffeine Gum was introduced in the United
States in 2013, but was voluntarily withdrawn after an announcement of an investigation by the FDA
of the health effects of added caffeine in foods.[145]

Inhalants
Taking caffeine by inhalation was under scrutiny by some U.S. lawmakers in 2011. [146]

Combinations with other drugs

Some beverages combine alcohol with caffeine to create a caffeinated alcoholic drink. The
stimulant effects of caffeine may mask thedepressant effects of alcohol, potentially reducing the
user's awareness of their level of intoxication. Such beverages have been the subject
of bans due to safety concerns. In particular, United States Food and Drug Administration has
classified caffeine added to malt liquor beverages as an "unsafe food additive". [147]

Ya ba contains a combination of methamphetamine and caffeine.

Decaffeination

Main article: Decaffeination

Fibrous crystals of purified caffeine. Dark field light microscope image, the image covers an area of approx. 7 x
11mm.

Extraction of caffeine from coffee, to produce caffeine and decaffeinated coffee, can be performed
using a number of solvents.Benzene, chloroform, trichloroethylene, and dichloromethane have all
been used over the years but for reasons of safety, environmental impact, cost, and flavor, they have
been superseded by the following main methods:

Water extraction: Coffee beans are soaked in water. The water, which contains many other
compounds in addition to caffeine and contributes to the flavor of coffee, is then passed
through activated charcoal, which removes the caffeine. The water can then be put back with the
beans and evaporated dry, leaving decaffeinated coffee with its original flavor. Coffee
manufacturers recover the caffeine and resell it for use in soft drinks and over-the-counter
caffeine tablets.[148]

Supercritical carbon dioxide extraction: Supercritical carbon dioxide is an excellent

nonpolar solvent for caffeine, and is safer than the organic solvents that are otherwise used. The
extraction process is simple: CO2 is forced through the green coffee beans at temperatures
above 31.1 C and pressures above 73 atm. Under these conditions, CO2 is in a
"supercritical" state: It has gaslike properties that allow it to penetrate deep into the beans but
also liquid-like properties that dissolve 9799% of the caffeine. The caffeine-laden CO 2 is then
sprayed with high pressure water to remove the caffeine. The caffeine can then be isolated
by charcoal adsorption (as above) or by distillation,recrystallization, or reverse osmosis.[148]

Extraction by organic solvents: Certain organic solvents such as ethyl acetate present
much less health and environmental hazard than chlorinated and aromatic organic solvents
used formerly. Another method is to use triglyceride oils obtained from spent coffee grounds. [148]

"Decaffeinated" coffees do in fact contain caffeine in many cases some commercially available
decaffeinated coffee products contain considerable levels. One study found that decaffeinated coffee

contained 10 mg of caffeine per cup, compared to approximately 85 mg of caffeine per cup for
regular coffee.[149]

History
Discovery and spread of use

Coffeehouse in Palestine, circa 1900

Main articles: History of chocolate, History of coffee, History of tea and History of yerba mate
According to Chinese legend, the Chinese emperor Shennong, reputed to have reigned in about
3000 BCE, accidentally discovered tea when he noted that when certain leaves fell into boiling
water, a fragrant and restorative drink resulted.[150] Shennong is also mentioned in Lu Yu's Cha Jing, a
famous early work on the subject of tea.[151]
The earliest credible evidence of either coffee drinking or knowledge of the coffee tree appears in the
middle of the fifteenth century, in theSufi monasteries of the Yemenin southern Arabia.
[152]

From Mocha, coffee spread to Egypt and North Africa, and by the 16th century, it had reached the

rest of the Middle East, Persia and Turkey. From the Middle East, coffee drinking spread to Italy,
then to the rest of Europe, and coffee plants were transported by the Dutch to the East Indies and to
the Americas.[153]
Kola nut use appears to have ancient origins. It is chewed in many West African cultures, individually
or in a social setting, to restore vitality and ease hunger pangs.
The earliest evidence of cocoa bean use comes from residue found in an ancient Mayan pot dated
to 600 BCE. Also, chocolate was consumed in a bitter and spicy drink called xocolatl, often
seasoned with vanilla, chile pepper, and achiote. Xocolatl was believed to fight fatigue, a belief
probably attributable to the theobromine and caffeine content. Chocolate was an important luxury
good throughout pre-Columbian Mesoamerica, and cocoa beans were often used as currency.[citation
needed]

Xocolatl was introduced to Europe by the Spaniards, and became a popular beverage by 1700. The
Spaniards also introduced the cacao tree into the West Indies and thePhilippines. It was used
in alchemical processes, where it was known as "black bean".[citation needed]
The leaves and stems of the yaupon holly (Ilex vomitoria) were used by Native Americans to brew
a tea called asi or the "black drink".[154] Archaeologists have found evidence of this use far into
antiquity,[155] possibly dating to Late Archaic times.[154]

Chemical identification, isolation, and synthesis

Pierre Joseph Pelletier

In 1819, the German chemist Friedlieb Ferdinand Runge isolated relatively pure caffeine for the first
time; he called it "Kaffebase" (i.e. a base that exists in coffee).[156] According to Runge, he did this at
the behest of Johann Wolfgang von Goethe.[157][158] In 1821, caffeine was isolated both by the French
chemist Pierre Jean Robiquet and by another pair of French chemists, Pierre-Joseph
Pelletier and Joseph Bienaim Caventou, according to Swedish chemist Jns Jacob Berzelius in his
yearly journal. Furthermore, Berzelius stated that the French chemists had made their discoveries
independently of any knowledge of Runge's or each other's work. [159] However, Berzelius later
acknowledged Runge's priority in the extraction of caffeine, stating: [160] "However, at this point, it
should not remain unmentioned that Runge (in his Phytochemical Discoveries, 1820, pages 146
147) specified the same method and described caffeine under the name Caffeebase a year earlier
than Robiquet, to whom the discovery of this substance is usually attributed, having made the first
oral announcement about it at a meeting of the Pharmacy Society in Paris."
Pelletier's article on caffeine was the first to use the term in print (in the French form Cafine from
the French word for coffee: caf).[161] It corroborates Berzelius's account:
See Tfm

Caffeine, noun (feminine). Crystallizable substance discovered in coffee in 1821 by Mr. Robiquet.
During the same period while they were searching for quinine in coffee because coffee is
considered by several doctors to be a medicine that reduces fevers and because coffee belongs to

the same family as the cinchona [quinine] tree on their part, Messrs. Pelletier and Caventou
obtained caffeine; but because their research had a different goal and because their research had
not been finished, they left priority on this subject to Mr. Robiquet. We do not know why Mr. Robiquet
has not published the analysis of coffee which he read to the Pharmacy Society. Its publication
would have allowed us to make caffeine better known and give us accurate ideas of coffee's
composition ...
Robiquet was one of the first to isolate and describe the properties of pure caffeine, [162] whereas
Pelletier was the first to perform an elemental analysis.[163]
In 1827, M. Oudry isolated "thine" from tea,[164] but it was later proved by Mulder[165] and by Carl
Jobst[166] that theine was actually caffeine.[158]
In 1895, German chemist Hermann Emil Fischer (18521919) first synthesized caffeine from its
chemical components (i.e. a "total synthesis"), and two years later, he also derived the structural
formula of the compound.[167] This was part of the work for which Fischer was awarded the Nobel
Prize in 1902.[168]

Society and culture

Consumption
Global consumption of caffeine has been estimated at 120,000 tonnes per year, making it the world's
most popular psychoactive substance. This amounts to one serving of a caffeinated beverage for
every person every day.[169]

Governments
Because it was recognized that coffee contained some compound that acted as a stimulant, first
coffee and later also caffeine has sometimes been subject to regulation. For example, in the 16th
century Islamists in Mecca and in the Ottoman Empire made coffee illegal for some classes. [170][171]
[172]

Charles II of England tried to ban it in 1676,[173][174]Frederick II of Prussia banned it in 1777,[175]

[176]

and coffee was banned in Sweden at various times between 1756 and 1823.

In 1911, caffeine became the focus of one of the earliest documented health scares, when the US
government seized 40 barrels and 20 kegs of Coca-Cola syrup in Chattanooga, Tennessee, alleging
the caffeine in its drink was "injurious to health".[177] Although the judge ruled in favor of Coca-Cola,
two bills were introduced to the U.S. House of Representatives in 1912 to amend the Pure Food and
Drug Act, adding caffeine to the list of "habit-forming" and "deleterious" substances, which must be
listed on a product's label.[178][unreliable source?] The Food and Drug Administration (FDA) in the United States
currently allows only beverages containing less than 0.02% caffeine;[161] but caffeine powder, which
is sold as a dietary supplement, is unregulated.[162]

Religions

Some Seventh-day Adventists, Church of God (Restoration) adherents, and Christian Scientists do
not consume caffeine.[citation needed] Some from these religions believe that one is not supposed to
consume a non-medical, psychoactive substance, or believe that one is not supposed to consume a
substance that is addictive. The Church of Jesus Christ of Latter-day Saints has said the following
with regard to caffeinated beverages: "With reference to cola drinks, the Church has never officially
taken a position on this matter, but the leaders of the Church have advised, and we do now
specifically advise, against the use of any drink containing harmful habit-forming drugs under
circumstances that would result in acquiring the habit. Any beverage that contains ingredients
harmful to the body should be avoided."[179]
Gaudiya Vaishnavas generally also abstain from caffeine, because they believe it clouds the mind
and over-stimulates the senses. To be initiated under a guru, one must have had no caffeine,
alcohol, nicotine or other drugs, for at least a year.[citation needed]
Caffeinated beverages are widely consumed by Muslims today. In the 16th century, some Muslim
authorities made unsuccessful attempts to ban them as forbidden "intoxicating beverages"
under Islamic dietary laws.[180][181]

Black Tea
Caffeine Levels

42mgCAFFEINE
per fl. oz cup
mlfl. oz

CAFFEINE LEVEL

MODERATE
Safe Amount ? Compare

Incorrect? Send Feedback

Caffeine in Tea varies quite a bit. The longer the tea (or tea bag) is steeped in
water, the more caffeine will be present.
Most tea manufacturers do not list caffeine amounts on labels (one exception is
Lipton regular tea at 55mg per serving).
The amount listed above is an average amount taken from various laboratory
tests. Originally we listed an amount (47mg/8 fl oz brew) taken from the USDA.
However more recent lab tests show this amount to be lower.
The following table lists recent lab test results for tea bags steeped in 6oz cups of
water.
1 Min Steep

3 Min Steep

5 Min Steep

Time

Time

Time

Lipton Decaf*

1.8mg

2.7mg

3.1mg

Lipton Regular*

17mg

38mg

47mg

Stash Darjeeling Black

14mg

22mg

27mg

Tea

Stash Earl Grey Black

24mg

41mg

47mg

Tazo Awake

59mg

59mg

61mg

Tazo Earl Grey

19mg

22mg

29mg

Twinings Earl Grey

19mg

22mg

25mg

14mg

22mg

25mg

Twinings Irish Breakfast

17mg

24mg

30mg

Twinings Lady Grey

14mg

29mg

30mg

Twinings Prince of Wales

14mg

26mg

29mg

19mg

39mg

49mg

Twinings English
Breakfast

Two Leavs and a Bud

Darjeeling

*Lipton Tea publishes slightly different amounts, which we have summarized

here.
Zest Black Tea has 150 mg of caffeine, but it is infused with extra caffeine.

What About Herbal Teas?

So-called herbal teas aren't actually tea at all, but a collection of other herbs and
flavors. Herbal teas do NOT contain caffeine.

What About Green Tea?

Green Tea contains less caffeine than black tea. However it also is affected by
brew time. The longer you leave your bag in the cup, the more caffeine you will
get. See more about caffeine in green tea.

Where To Buy Black Tea

Lipton Black Tea, Loose 8 oz

Price: $12.96 $4.50Available from Amazon / Lipton

Davidson's Tea Bulk, English Breakfast, 16-Ounce Bag

Price: $15.00 $15.00Available from Amazon / Davidson's Tea

Numi Organic Tea Chinese Breakfast Yunnan Black Tea, Loose Leaf, 16
Ounce Bag
Price: $21.75 $21.75Available from Amazon / Numi

Coffee Bean Direct Orange Pekoe Loose Leaf Black Tea, 2 Pound Bag
Price: $16.16 $13.70Available from Amazon / Coffee Bean Direct

Harney & Sons Paris Loose Leaf Tea, 4 Ounce Tin

Price: $7.88 $7.50Available from Amazon / Harney & Sons

What You Should Know About Black Tea

TEA ESSENTIALS

Pin it
Beyond the label of black versus green tea, each of these categories includes a rich array of
aromas and flavors. Today we're taking a closer look at black tea in its various forms, from

smoky and chocolatey to bright and citrusy. Wondering when to add milk, or which variety
is better for iced tea? Step right in...
What is black tea?

Black tea comes from a shrub called Camellia sinensis. The aroma, taste, and color of black
tea depend on factors such as the species of Camellia; the country, region, and garden or
estate where it was grown; the year and season of harvest; the manufacturing method; and
the grade. Today, black tea is primarily grown in China, India, Sri Lanka, and Kenya.
To manufacture black tea, the leaves are plucked and withered to reduce moisture. Then,
the leaves may be left whole and rolled, known as orthodox process, or they may undergo a
cut-tear-curl (CTC) process. Finally, the leaves are oxidized and dried. (The oxidation
process is sometimes referred to as fermentation but this is a misnomer.) Black tea leaves
are more oxidized than white, green, and oolong teas and generally have a stronger flavor
and aroma.
In China this tea is known as "red tea" (qi hong or hong cha), referring to the color of its
brew, whereas "black tea" refers to pu-erh tea.

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Types of black tea

Some of the major types of black tea include:

Assam: Grown in northeastern India, this tea is full-bodied, dark, and malty. It is
used in many tea blends such as masala chai, English Breakfast, and Irish Breakfast. Good
with milk and sugar.

Ceylon: Grown in the mountains of Sri Lanka, this tea is lively and bright with citrus
notes.

Darjeeling: Grown on a small number of estates in India's Himalayas, this prized

tea is delicate, floral, and fruity. It is known as the "Champagne of tea." Best served without
milk or sugar.

Keemun: Grown in the Anhui province of eastern China, this tea is full-bodied,
smooth, and fruity.

Nilgiri: Grown in southern India, this tea is fragrant with low tannins and
astringency. Makes a good iced tea.

Lapsang Souchong: Grown in the Fujian province of southeastern China, this

deep, smoky, robust tea is smoked over pine or spruce wood.

Yunnan: Grown in southwestern China, this tea is rich and sweet with chocolate
notes.
Black tea blends

Some of the major black tea blends include:

Earl Grey: Black tea flavored with bergamot oil, which gives it a citrus fragrance.
Often made with Keemun and/or Ceylon teas.

English breakfast: A strong blend that goes well with milk and sugar. Often made
with Ceylon tea.

Irish breakfast: A robust blend that goes well with milk and sugar. Often made
with Assam tea.

Masala chai: An Indian black tea brewed with spices such as black pepper,
cardamom, cinnamon, cloves, and ginger.

Russian caravan: An aromatic, smoky blend. Often made with Keemun and
Lapsang Souchong teas.
Grades of black tea

Black tea is graded according to the size of the leaf, which can affect its brewing rate and
how nuanced or pungent the flavor is. One is not necessarily better than the other; for
example, fannings from a high quality tea may taste better than broken leaves from a lower
quality tea.

Whole leaf: Whole leaf tea requires greater skill to pluck and process and accounts
for only about 5 to 10 percent of all tea produced. It is sold as looseleaf tea or sometimes in
tea bags.

Broken leaf: This is sold as looseleaf tea or used in tea bags.

Fannings: Leftover from the processing of higher grade teas, these small leaf pieces
are used in tea bags.

Dust: Like fannings, these leftover leaf particles are used in tea bags. They have the
fastest brewing time and least nuanced flavor.
What is Orange Pekoe?

Orange Pekoe is not a quality or flavor of tea but rather a leaf size, and the term is used
when discussing teas from India or Sri Lanka. Tea grades can get very specific within each of
the major categories listed above, for example: OP (Orange Pekoe; whole leaves), FOP
(Flowery Orange Pekoe; extra-large whole leaves), and BOP (Broken Orange Pekoe; broken
leaves). For a complete list of abbreviations see this Wikipedia entry on Tea leaf grading.