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Caffeine

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Caffeine
2D structure of caffeine
3D structure of caffeine
Clinical data
Pronunciation/kæˈfiːn, ˈkæfiːn/
SynonymsGuaranine
Methyltheobromine
1,3,7-Trimethylxanthine
7-methyltheophylline[6] Theine
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: A
Dependence
liability		Physical: low–moderate[1][2][3][4]
Psychological: low[5]
Addiction
liability		Low[4] / none[1][2][3]
Routes of
administration		By mouth, insufflation, enema, rectal, intravenous
Drug classStimulant
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability99%[8]
Protein binding25–36%[7]
MetabolismPrimary: CYP1A2[7]
Minor: CYP2E1,[7] CYP3A4,[7]
CYP2C8,[7] CYP2C9[7]
MetabolitesParaxanthine (84%)
Theobromine (12%)
Theophylline (4%)
Onset of action~1 hour[8]
Elimination half-lifeAdults: 3–7 hours[7]
Infants (full term): 8 hours[7]
Infants (premature): 100 hours[7]
Duration of action3–4 hours[8]
ExcretionUrine (100%)
Identifiers
IUPAC name
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
E number
ECHA InfoCard
Chemical and physical data
FormulaC8H10N4O2
Molar mass194.19 g·mol−1
3D model (JSmol)
Density1.23 g/cm3
Melting point235 to 238 °C (455 to 460 °F) (anhydrous)[9][10]
SMILES
InChI
Coffee plant (Coffea arabica), with fruits. The fruits, which are used to make coffee, contain caffeine.

Caffeine is a central nervous system (CNS) stimulant. It is found in parts of plants, for example tea leaves and coffee beans. Its artificial form is also used in some soft drinks and energy drinks. It is the world's most popular psychoactive drug, and is legal in all of the world.[11]

Caffeine Media

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org.apache.batik.transcoder.SVGAbstractTranscoder.transcode(SVGAbstractTranscoder.java:228) at org.apache.batik.transcoder.image.ImageTranscoder.transcode(ImageTranscoder.java:92) at org.apache.batik.transcoder.XMLAbstractTranscoder.transcode(XMLAbstractTranscoder.java:142) at org.apache.batik.transcoder.SVGAbstractTranscoder.transcode(SVGAbstractTranscoder.java:158) at org.apache.batik.apps.rasterizer.SVGConverter.transcode(SVGConverter.java:1008) at org.apache.batik.apps.rasterizer.SVGConverter.execute(SVGConverter.java:719) at org.apache.batik.apps.rasterizer.Main.execute(Main.java:956) at org.apache.batik.apps.rasterizer.Main.main(Main.java:1009) Caused by: org.apache.batik.bridge.BridgeException: file:/var/www/html/w/images/temp/svg_c6f48435420371565442714a/Main_symptoms_of_Caffeine_overdose.svg:0 The URI "data:image/gif;base64,R0lGODlhIwHhAPcAAAAAACsVFDQdGjUfIDgiHTwqJz4sMD0xLEItKkMuMUkyLUUzMkY5NkY7Okw1 Mko3OEw5NEs7OVIzLVI1MVM6NVQ9O1g3NFk6Nlw9OmA+NmE+O1U+QFw+QExAPVdANlRAPF1ANlxB 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    Primary symptoms of caffeine intoxication

  • Caffeine's primary mechanism of action is as an adenosine receptor antagonist in the brain.

  • Caffeine is metabolized in the liver via a single demethylation, resulting in three primary metabolites, paraxanthine (84%), theobromine (12%), and theophylline (4%), depending on which methyl group is removed.

  • Urinary metabolites of caffeine in humans at 48 hours post-dose

  • One biosynthetic route of caffeine, as performed by Camellia and Coffea species

  • One laboratory synthesis of caffeine

  • Fibrous crystals of purified caffeine. Dark-field microscopy image, about 7 mm × 11 mm.

  • Torrefied coffee beans

  • No-Doz 100 mg caffeine tablets

  • Coffeehouse in Palestine, c. 1900

Sources

Caffeine is naturally found in the fruits, leaves and beans of coffee, cacao, guarana and tea plants.

The plants use caffeine as a pesticide. This is a chemical that kills insects if they eat the plant. It is the way the plant protects itself.

Caffeine was first extracted from cocoa beans into its purest form which is a white powder and the word originated from the German word “Kaffee” and the French word “café” which both mean caffeine.[12]

When it comes from the guarana plant it is called guaranine, when it comes from a tea plant, it is called theine, and in the mate drink it is called mateine (this drink is an infusion made with Yerba mate).

What caffeine is

Caffeine molecule

Caffeine is a stimulant drug. A stimulant is a drug that increases body actions like heart rate, blood pressure, and metabolism. It makes a person more awake and alert.

Caffeine also is a diuretic. This means it makes a person make more urine (the waste liquid a person makes).

The caffeine chemical is called a xanthine alkaloid. This is a group of chemicals that are stimulants. Some xanthine alkaloids (like theophylline) are used to help asthma.

What caffeine is used for

The biggest use of caffeine is as a stimulant. People drink coffee and other drinks with caffeine to stay awake.

In the beginning caffeine was found to relieve hunger, so it was used for weight loss. That did not last because people were using too much. Caffeine can be dangerous when not used in the right way.

Doctors sometimes use caffeine as a medicine.[13] It is added to analgesics (drugs used for pain).[13] This can improve their effect on headaches and other pain.[13] It is sometimes used to help premature babies (babies born very early) to breathe.[14] The short-term risk of this treatment seems to be that the babies treated gain less weight than usual.[15] Caffeine is sometimes given to people after a lumbar puncture.[16] This is when a needle is pushed between the bones of the lower back, normally to check for illnesses[16] like meningitis.[17]

Problems with caffeine

Caffeine is a problem for spiders. The image above shows a spiderweb which was woven by a normal spider. The image below shows a web of a spider that had received Caffeine in an experiment

The largest problem with caffeine is addiction. This is when people get bad symptoms when they do not have the drug. When people have withdrawal (feel bad because they do not have the drug) they drink more. This makes them feel better. But if they cannot get more, they are likely to feel some of the symptoms listed below:

  • Headaches
  • Being tired or need to sleep
  • Caffeine can prevent sleep and in the long-term alters brain functions
    • Sleep deprivation leads to a weakened connectivity between the amygdala and medial prefrontal cortex which regulate mood and emotion.
      • This causes the consumer to feel irritable, tired, restlessness, and anxious.
  • Nausea (feeling like vomiting)

Caffeine can also hurt people if they drink a lot at once. If a person consumed 10-13 grams of caffeine quickly, between 80 and 100 cups of coffee, they would overdose and may even die.[18] Caffeine overdose is a medical diagnosis. It is called: Caffeine-Induced Organic Mental Disorder or Caffeine Intoxication. People with this can have these symptoms:

  • Very bad feelings like:
    • Paranoia (feeling as if people are about to hurt the person)
    • Restlessness or nervousness (with the person feeling like he cannot sit down or rest)
    • Anxiety (very bad worry)
  • Muscle movements that cannot be stopped
  • Very fast heart rate
  • Abnormal heart rhythms (even heart stopping)
  • Very high blood pressure
  • Vomiting
  • Confusion (not knowing who the person is or where he/she is)

Caffeine helps for

Caffeine also has some strong advantages:[19]

How much caffeine is safe

250–300 mg of caffeine a day is a moderate amount. That is as much caffeine that is in three cups of coffee (8oz each cup). More than 750–1000 mg a day is a significant amount, but is very unlikely to kill someone. The Lethal Dose 50 of caffeine is 192 mg per kilogram, in rats. In humans, it is between 150 and 200 mg per kilogram (70-90 per pound.)

Caffeine is in many drinks and foods. This is approximate amounts of caffeine in some food and drink:

  • Brewed coffee – 40 to 220 mg in a cup
  • Instant coffee – 30 to 120 mg in a cup
  • Decaffeinated coffee (with most caffeine taken out) – 3 to 5 mg in a cup
  • Tea – 20 to 110 mg in a cup
  • Soda drinks with caffeine – 36 to 90 mg in 12 ounces. Some people think that soft drinks which are light in color do not contain caffeine. This is not always true.
  • Milk chocolate – 3 to 6 mg in an ounce
  • Bittersweet chocolate – 25 mg in an ounce

One ounce – abbreviated oz – is 30 ml.

A 'cup' is 8 oz (240 ml.)

Different ways to get 200mg of caffeine

Caffeine equivalents[20][21]
In general, each of the following contains approximately 200 milligrams[broken anchor] of caffeine:

Notes:

A fluid ounce is between 28 and 30 millilitres.

a. There may also be large amounts of other chemicals, similar to caffeine in chocolate and other products of cacao. There is theobromine in cacao, for example. These substances can have effects similar to those of caffeine.

b. Most tea drunk in North America is not very strong. The figures are for this kind of tea. The tea drunk in most other places of the world is stronger; for these kinds of tea, the figures are probably too small.

References

  1. ↑ 1.0 1.1 Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2009). New York: McGraw-Hill Medical. p. 375. ISBN 978-0-07-148127-4.
  2. ↑ 2.0 2.1 [Caffeine at Google Books Karch's pathology of drug abuse] (2009). Boca Raton: CRC Press. p. 229–230. ISBN 978-0-8493-7881-2.
  3. ↑ 3.0 3.1 American Psychiatric Association. Substance-Related and Addictive Disorders (2013)American Psychiatric Publishing. p. 1–2. Retrieved 10 July 2015.
  4. ↑ 4.0 4.1 Introduction to Pharmacology (2007). Abingdon: CRC Press. p. 222–223. ISBN 978-1-4200-4742-4.
  5. ↑ A critical review of caffeine withdrawal: empirical validation of symptoms and signs, incidence, severity, and associated features. Psychopharmacology 176 (1) (October 2004). p. 1–29. doi:10.1007/s00213-004-2000-x.
  6. ↑ Caffeine. ChemSpider. Retrieved 16 November 2021.
  7. ↑ 7.0 7.1 7.2 7.3 7.4 7.5 7.6 7.7 7.8 Caffeine. DrugBank (16 September 2013)University of Alberta. Retrieved 8 August 2014.
  8. ↑ 8.0 8.1 8.2 Caffeine augments the antidepressant-like activity of mianserin and agomelatine in forced swim and tail suspension tests in mice. Pharmacological Reports 68 (1) (February 2016). p. 56–61. doi:10.1016/j.pharep.2015.06.138.
  9. ↑ Caffeine. Pubchem CompoundNCBI. Retrieved 16 October 2014.
  10. ↑ Caffeine. ChemSpiderRoyal Society of Chemistry. Retrieved 16 October 2014.
  11. ↑ What's your poison: caffeine. Australian Broadcasting Corporation. 1997. http://www.abc.net.au/quantum/poison/caffeine/caffeine.htm. Retrieved 15 January 2014. 
  12. ↑ "History and Background" (in en-US). Caffeine. 2012-09-12. https://caffeineandyou.wordpress.com/historyandbackground/. Retrieved 2018-11-18. 
  13. ↑ 13.0 13.1 13.2 Caffeine (in en-us). The Nutrition Source (2020-07-30). Retrieved 2024-12-27.
  14. ↑ Moschino, Laura. Caffeine in preterm infants: where are we in 2020?. National Library of Medicine (2020-03-01). Retrieved 2024-12-27.
  15. ↑ Schmidt, B. Caffeine therapy for apnea of prematurity. New England Journal of Medicine 354 (20) (May 18, 2006). p. 2112–21. doi:10.1056/NEJMoa054065.
  16. ↑ 16.0 16.1 Lumbar Puncture - What You Need to Know (in en). Drugs.com. Retrieved 2024-12-27.
  17. ↑ What is a lumbar puncture? (in en). www.meningitis.org. Retrieved 2024-12-27.
  18. ↑ Can caffeine kill you?. Livescience.com (25 September 2012). Retrieved 19 February 2016.
  19. ↑ (in en-US) The Advantages and Disadvantages Of Drinking Coffee | Coffee Corner. 2017-10-26. https://coffeecorner.com/general/advantages-disadvantages-drinking-coffee/. Retrieved 2017-12-03. 
  20. ↑ Caffeine Content of Food and Drugs. Nutrition Action Health Newsletter (December 1996)Center for Science in the Public Interest. Retrieved 2006-08-22.
  21. ↑ Caffeine Content of Beverages, Foods, & Medications (July 7, 2006)The Vaults of Erowid. Retrieved 2006-08-22.

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