Compound Summary

General Compound Information

caffeine

Description
Caffeine is a trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee. It has a role as a central nervous system stimulant, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an adenosine receptor antagonist, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, a ryanodine receptor agonist, a fungal metabolite, an adenosine A2A receptor antagonist, a psychotropic drug, a diuretic, a food additive, an adjuvant, a plant metabolite, an environmental contaminant, a xenobiotic, a human blood serum metabolite, a mouse metabolite and a mutagen. It is a purine alkaloid and a trimethylxanthine.
Synonyms
caffeine;  58-08-2;  Guaranine;  1,3,7-Trimethylxanthine;  Methyltheobromine;
FlavorDB ID
592
PUBCHEM ID
2519
Molecular Weight
194.19
Molecular Formula
C8H10N4O2
Openeye Can Smiles
CN1C=NC2=C1C(=O)N(C(=O)N2C)C
IUPAC Inchikey
RYYVLZVUVIJVGH-UHFFFAOYSA-N
Similarity
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Compound Classification
  • ClassyFire Ontology
Compound Quality
CATEGORY QUALITY THRESHOLD OCCURENCE REFERENCE
taste bitter 6.800e+2 µmol/L coffee details
taste bitter 5.000e+2 µmol/L cocoa details
taste bitter 7.500e+2 µmol/L cocoa nibs details
Compound Toxicity and Food Additive Safety (OFAS)
Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
The oral LD50 of caffeine in rats is 192 mg/kg.[MSDS] An acute fatal overdose of caffeine in humans is about 10-14 grams (equivalent to 150-200 mg/kg of body weight).[T722] **Caffeine overdose** In the case of caffeine overdose, seizures may occur, as caffeine is a central nervous system stimulant. It should be used with extreme caution in those with epilepsy or other seizure disorders.[L9851] Symptoms of overdose may include nausea, vomiting, diarrhea, and gastrointestinal upset. Intoxication with caffeine is included in the World Health Organization's International Classification of Diseases (ICD-10). Agitation, anxiety, restlessness, insomnia, tachycardia, tremors, tachycardia, psychomotor agitation, and, in some cases, death can occur, depending on the amount of caffeine consumed. Overdose is more likely to occur in individuals who do not consume caffeine regularly but consume energy drinks.[A187721] **Overdose management** For a mild caffeine overdose, offer symptomatic treatment. In the case of a severe overdose, intubation for airway protection from changes in mental status or vomiting may be needed. Activated charcoal and hemodialysis can prevent further complications of an overdose and prevent absorption and metabolism. Benzodiazepine drugs can be administered to prevent or treat seizures. IV fluids and vasopressors may be necessary to combat hypotension associated with caffeine overdose. In addition, magnesium and beta blocking drugs can be used to treat arrhythmias that may occur, with defibrillation and resuscitation if the arrhythmias are lethal. Follow local ACLS protocols.[T716]
Source: DrugBank or Hazardous Substances Data Bank (HSDB)
Food Additive Safety (OFAS)
CAFFEINE is used for FLAVORING AGENT OR ADJUVANT. More food additive safty information please view GRAS report.
EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Caffeine
Receptors
Receptor REFERENCE EC50 [µM] Effective Concentration [µM]
TAS2R7 details Activated 300.00
TAS2R10 details Activated 300.00
TAS2R14 details Activated 300.00
TAS2R43 details Activated 300.00
TAS2R46 details Activated 300.00
Consensus Spectra
Spectrum Type Spectrum View Description Polarity
Experimental GCMS view GCMS positive
Experimental LCMS view LCMS_Positive positive
Experimental LCMS view LCMS_Negative negative