CAS No.: 58-08-2 Formula: C8H10N4O2 Molecular Weight: 194.19100
Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class. It is the world's most widely consumed psychoactive drug. Unlike many other psychoactive substances, it is legal and unregulated in nearly all parts of the world. There are several known mechanisms of action to explain the effects of caffeine. The most prominent is that it reversibly blocks the action of adenosine on its receptor and consequently prevents the onset of drowsiness induced by adenosine. Caffeine also stimulates certain portions of the autonomic nervous system.
Caffeine is a bitter, white crystalline purine, a methylxanthine alkaloid, and is chemically related to the adenine and guanine bases of 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 and confers on them several survival and reproductive benefits. The most well known source of caffeine is the coffee bean, a misnomer for the seed of Coffea plants. Beverages containing caffeine are ingested to relieve or prevent drowsiness and to improve performance. To make these drinks, caffeine is extracted by steeping the plant product in water, a process called infusion. Caffeine-containing drinks, such as coffee, tea, and cola, are very popular; in 2005, 90% of North American adults consumed caffeine daily.
Caffeine can have both positive and negative health effects. It can treat and prevent the premature infant breathing disorders bronchopulmonary dysplasia of prematurity and apnea of prematurity. Caffeine citrate is on the WHO Model List of Essential Medicines. It may confer a modest protective effect against some diseases, including Parkinson's disease and certain types of cancer. One meta-analysis concluded that cardiovascular disease such as coronary artery disease and stroke is less likely with 3–5 cups of non-decaffeinated coffee per day but more likely with over 5 cups per day. 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. Caffeine 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. 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).
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 doses of under 500 milligrams per day. A cup of coffee contains 80–175 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 50–100 ordinary cups of coffee to reach a lethal dose. However pure powdered caffeine, which is available as a dietary supplement, can be lethal in tablespoon-sized amounts.
Chemical Name | Caffeine |
Synonyms | 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl-; CAFFEIN; Miudol; trimethylxanthine; Kofein; Theine; tirend; THEIN; Stim; COFFEIN; No-Doz; Nodaca; 1,3,7-trimethylxanthine; 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; |
CAS No. | 58-08-2 |
Molecular Formula | C8H10N4O2 |
Molecular Weight | 194.19100 |
PSA | 61.82000 |
LogP | -1.02930 |
Appearance & Physical State | white to light yellow crystal powder |
Density | 1.23 |
Boiling Point | 178°C |
Melting Point | 234-236.5 °C(lit.) |
Flash Point | 178°C |
Water Solubility | 20 g/L (20 ºC) |
Stability | Stable. Incompatible with strong acids, strong bases, strong oxidizing agents, iodine, silver salts, tannins. Weakly light sensitive in solution. |
Storage Condition | 2-8°C |
RTECS | EV6475000 |
Hazard Class | 6.1 |
Safety Statements | S16; S36/37; S45 |
HS Code | 2939300010 |
WGK Germany | 1 |
Packing Group | III |
RIDADR | UN 1544 6.1/PG 3 |
Risk Statements | R22; R25 |
Hazard Codes | Xn; T |
3,4,5,7-Tetrahydro-1,3,7-trimethyl-10-syn-phenyl-11-anti-(trans-2-phenylethenyl)-4,5-ethano-1H-purin-2,6-dion→Caffeine+1,4-diphenylbutadiene
3,4,5,7-Tetrahydro-1,3,7-trimethyl-11-syn-phenyl-10-anti-(trans-2-phenylethenyl)-4,5-ethano-1H-purin-2,6-dion→Caffeine+1,4-diphenylbutadiene
[5aR-(5aα,6β,9β,10α)]-5,5a,6,9-Tetrahydro-1,3,5-trimethyl-6,9-diphenylpyrido[1,2-e]purin-2,4(1H,3H)-dion→Caffeine+1,4-diphenylbutadiene
[5aR-(5aα,6β,9β,10α)]-5,5a,6,9-Tetrahydro-1,3,5-trimethyl-6,9-diphenylpyrido[1,2-e]purin-2,4(1H,3H)-dion
3,4,5,7-Tetrahydro-1,3,7-trimethyl-10-syn-phenyl-11-anti-(trans-2-phenylethenyl)-4,5-ethano-1H-purin-2,6-dion
8-benzyl-1,3,7-trimethylpurine-2,6-dione
3,4,5,7-Tetrahydro-1,3,7-trimethyl-11-syn-phenyl-10-anti-(trans-2-phenylethenyl)-4,5-ethano-1H-purin-2,6-dion