Caffeine
Synonym(s):1,3,7-Trimethylxanthine;Caffeine
- CAS NO.:58-08-2
- Empirical Formula: C8H10N4O2
- Molecular Weight: 194.19
- MDL number: MFCD00005758
- EINECS: 200-362-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-30 15:45:59
What is Caffeine?
Absorption
Caffeine is rapidly absorbed after oral or parenteral administration, reaching peak plasma concentration within 30 minutes to 2 hours after administration. After oral administration, onset of action takes place within 45 to 1 hour. Food may delay caffeine absorption. The peak plasma level for caffeine ranges from 6-10mg/L. The absolute bioavailability is unavailable in neonates, but reaches about 100% in adults.
Toxicity
The oral LD50 of caffeine in rats is 192 mg/kg. An acute fatal overdose of caffeine in humans is about 10–14 grams (equivalent to 150–200 mg/kg of body weight).
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. 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.
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.
Description
Caffeine is an alkaloid purine belonging to the group of organic compounds called methylxanthines. Pure caffeine is a white, crystalline, bitter-tasting compound. Caffeine is found in a number of plants, principally coffee and tea plants, as well as cola and cacao nuts. In plants, caffeine functions as a natural pesticide to deter insects.
Description
Ah, caffeine. For many people, productivity at school, work, and home would slip without a morning dose of this alkaloid found in tea leaves, coffee beans, cocoa beans, and kola nuts. Caffeine acts as a central nervous system and respiratory stimulant and is also a diuretic.
Description
Caffeine is a purine alkaloid commonly found in coffee and tea. Several in vivo studies have demonstrated that topical and oral administration of caffeine exerts a photoprotective effect through various mechanisms. Specifically, caffeine has been demonstrated to induce apoptosis in DNA damaged epidermal cells and tumors while sparing normal tissue. Mouse models demonstrate that this apoptotic effect is secondary to increased expression of wild-type p53, a tumor suppressor gene that is commonly mutated in UV-related skin cancers. Moreover, caffeine also has a sunscreen-like effect and inhibits formation of UVB-induced thymine dimers and sunburn skin lesions.
Chemical properties
white to light yellow crystal powder
Chemical properties
Caffeine is the alkaloid 1,3,7-trimethylxanthine. It is one of the xanthine derivatives present up to 1.5% in seeds of coffee (Coffea arabica L.) and up to 5% in the leaves of tea (Camelia sinensis). It is a component of the beverages made from these plants. Caffeine is also a component of chocolate (Theobroma cacao) and the cola nut (Cola acuminata Schott and Endel. and related species), the extract of which is used in cola drinks. It is virtually odorless. Caffeine is added to cola-type beverages for its enhancement of flavor. Subtle and subliminal flavors are widely appreciated by consumers and caffeine has a modifying effect on other components of the beverage. The threshold for detecting the presence of caffeine in liquid foods varies depending on the nature of other substances present, but lies close to the level characteristic of currently produced cola-type beverages. The threshold for detection of caffeine in water has been shown to be 0.0095%; in liquid foods, 0.0184%. In one study, panelists could distinguish a solution containing 0.0058% caffeine from the control. The threshold for detecting taste difference between an aqueous solution of caffeine and a water control was also shown to be 0.005% caffeine and to distinguish bitterness, 0.011% caffeine. In aqueous solutions containing threshold and subthreshold concentrations of caffeine, sucrose, citric acid and salt, all compounds depressed the taste intensity of each other.*
Physical properties
Appearance: odorless silky needle-like crystal or crystal powder with the color of white or a little yellowish green. Solubility: weathering, easily dissolved in water or chloroform and slightly soluble in water, ethanol, or acetone, very slightly dissolved in ether. Melting point: 235–238?°C.
Originator
Caffedrine,Thompson Med.
Occurrence
Reported found in coffee and guarana.
History
Runge isolated caff eine from coffee in 1819. Caffeine derives its name from the Kaffa region of Ethiopia. Caffeine comes from the German kaffeine, which in turn is derived from the German word for coffee, kaffee. In 1827, a compound isolated from tea was named theine, but this was eventually shown to be caffeine.
The Uses of Caffeine
Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a stimulant drug and a reversible acetylcholinesterase inhibitor. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants. In humans, caffeine acts as a central nervous system stimulant, temporarily warding off drowsiness and restoring alertness. Caffeine is a cardiac and respiratory stimulant; diuretic. Caffeine is toxic at sufficiently high doses.
The Uses of Caffeine
CNS stimulant respiratory stimulant;adenosine receptors antagonist
The Uses of Caffeine
caffeine has a lipolytic effect on fatty cells, able to break down lipids and release fatty acids. given this ability and its draining properties, caffeine is used for skin firming and tightening. It is often incorporated into body product formulations targeting cellulite and slimming, as well as in eye creams that claim to reduce puffiness. Among its constituents are tannin and the alkaloid methylxanthine. Caffeine is a bitter-tasting, odorless white powder that occurs naturally in coffee, cola, guana paste, kola nuts, and tea. It is obtained as a by-product of decaffeinated coffee.
The Uses of Caffeine
Caffeine is a white powder or needles that are odorless and have a bitter taste. it occurs naturally in tea leaves, coffee, cocoa, and cola nuts. it is a food additive used in soft drinks for its mildly stimulat- ing effect and distinctive taste note. it is used in cola-type beverages and is optional in other soft drinks up to 0.02%.
The Uses of Caffeine
Caffeine is consumed in coffee, tea, cocoa,chocolate, and soft drinks. It occurs naturallyin the leaves of coffee, tea, and mate and in ′cola nuts. It is used in medicine and found inmany drugs. It is used as a cardiac stimulant.
The Uses of Caffeine
Caffeine has widespread therapeutic use. It is widely used in headache (migraine) remedies such as aspirin and other analgesics. Caffeine is a mild vasoconstrictor and its ability to constrict blood vessels serving the brain explains its use to relieve headache. Caffeine is a common substance in medications to treat apnea in premature infants. Apparently, the area of the brain controlling respiration in premature infants is not fully developed and caffeine helps to stimulate this portion of the brain. The combination of caffeine and ephedrine is used in dietary and athletic supplements, and their role as appetite suppressant and energy boosters has been extensively studied.
Indications
Caffeine is indicated for the short term treatment of apnea of prematurity in infants and off label for the prevention and treatment of bronchopulmonary dysplasia caused by premature birth. In addition, it is indicated in combination with sodium benzoate to treat respiratory depression resulting from an overdose with CNS depressant drugs. Caffeine has a broad range of over the counter uses, and is found in energy supplements, athletic enhancement products, pain relief products, as well as cosmetic products.
Background
Caffeine is a drug of the methylxanthine class used for a variety of purposes, including certain respiratory conditions of the premature newborn, pain relief, and to combat drowsiness. Caffeine is similar in chemical structure to Theophylline and Theobromine. It can be sourced from coffee beans, but also occurs naturally in various teas and cacao beans, which are different than coffee beans. Caffeine is also used in a variety of cosmetic products and can be administered topically, orally, by inhalation, or by injection.
The caffeine citrate injection, used for apnea of the premature newborn, was initially approved by the FDA in 1999. According to an article from 2017, more than 15 million babies are born prematurely worldwide. This correlates to about 1 in 10 births. Premature birth can lead to apnea and bronchopulmonary dysplasia, a condition that interferes with lung development and may eventually cause asthma or early onset emphysema in those born prematurely. Caffeine is beneficial in preventing and treating apnea and bronchopulmonary dysplasia in newborns, improving the quality of life of premature infants.
What are the applications of Application
Caffeine is an adenosine receptor antagonist and cAMP phosphodiesterase inhibitor
Definition
ChEBI: 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.
Indications
This product is included in the Pharmacopoeia of the People’s Republic of China (2015), the British Pharmacopoeia (2017), the United States Pharmacopeia (40), the Japanese Pharmacopoeia (17th ed.), the European Pharmacopoeia (9.0th ed.), the Indian Pharmacopoeia (2010), and the International Pharmacopoeia (5th ed.). Commonly used dosage forms of caffeine include tablet, powder, and injection. Mainly used dosage forms in the market include caffeine citrate tablets, amidopyrine caffeine tablets, amidopyrine caffeine, children acetaminophen aspirin caffeine tablets, ergotamine caffeine tablets, caffeine sodium benzoate injection, cafe bromine agent, etc.
Manufacturing Process
Caffeine was synthesized by the reaction N-chloromethylation of theophylline by action dimethylsulphate in dimethylsulfoxide.
brand name
NoDoz Caplets and Chewable Tablets (Bristol-Myers Products).
Therapeutic Function
Neurotropic, Central stimulant
Aroma threshold values
Detection at 29 to 300 ppm. Also see description.
Taste threshold values
See Description.
General Description
Odorless white powder or white glistening needles, usually melted together. Bitter taste. Solutions in water are neutral to litmus. Odorless.
Air & Water Reactions
Efflorescent in air. Water soluble.
Reactivity Profile
Caffeine may be hygroscopic. Aqueous solutions (1.12 mg/mL) are stable for three weeks at 41° F if protected from light. In normal room lighting and at room temperature, solutions are stable for 3 days. Solutions of Caffeine in water, DMSO, 95% ethanol or acetone should be stable for 24 hours under normal lab conditions. REACTIVITY: Caffeine may react with strong oxidizing agents. Caffeine is also incompatible with iodine, silver salts and tannins. Caffeine is a very weak base. Caffeine is decomposed by strong solutions of caustic alkalis.
Hazard
One grain or more is toxic, 200 μg/m L has been found to inhibit activity of the enzyme DNA polymerase. Use in soft drinks not to exceed 0.02%. Questionable carcinogen.
Health Hazard
Caffeine is a stimulant of the central nervoussystem. It eliminates fatigue and drowsiness. However, high doses cause gastrointestinal motility, restlessness, sleeplessness,nervousness, and tremor. Acute poisoningeffects include nausea, vomiting, headache,excitability, tremor, and sometimes, convulsive coma. Other symptoms may be respiratory depression, muscle contraction, distortedperception, and hallucination. Ingestion of15–20 g may be fatal to humans.
LD50 value, oral (mice): 127 mg/kg
LD50 value, oral (rabbits): 224 mg/kg
Animal studies indicate that caffeine athigh doses produces adverse reproductiveeffects, causing developmental abnormalities. It tested negative in the histidine reversion–Ames and TRP reversion tests.
Fire Hazard
Flash point data for Caffeine are not available; however, Caffeine is probably combustible.
Biological Activity
Central nervous system stimulant. Antagonist at A 1 and A 2A adenosine receptors and inhibitor of cyclic nucleotide phosphodiesterases. Mobilises calcium from intracellular stores and inhibits benzodiazepine binding to GABA receptors.
Pharmacokinetics
Caffeine stimulates the central nervous system (CNS), heightening alertness, and sometimes causing restlessness and agitation. It relaxes smooth muscle, stimulates the contraction of cardiac muscle, and enhances athletic performance. Caffeine promotes gastric acid secretion and increases gastrointestinal motility. It is often combined in products with analgesics and ergot alkaloids, relieving the symptoms of migraine and other types of headaches. Finally, caffeine acts as a mild diuretic.
Clinical Use
The commonly used clinical preparations include caffeine sodium benzoate and ergotamine caffeine. The preparation of caffeine sodium benzoate (injection) is constituted of 0.12?g/ml of caffeine, 0.13?g/ml of sodium benzoate, and cafe bromine mixture (oral liquid). Clinically, it can be used for migraine headaches, cerebral artery dilated headache, or headache caused by histamine. However, it is invalid in the prevention of headaches. The adverse reactions include nausea, vomiting, abdominal pain, and fatigue. Other common symptoms include numbness and tingling of the hands, toes, and face and swelling of the foot and lower limb. Overdose causes severe poisoning, mental disorder, ataxia, convulsions, gray chills of the hand and foot, sensory disturbance, and even death due to coma and respiratory paralysis. Caffeine citrate preparation, including injection and oral solution, is the only internationally approved drug for the treatment of premature infant apnea.
Safety Profile
A human poison by ingestion. An experimental poison by ingestion, subcutaneous, intraperitoneal, intramuscular, rectal, and intravenous routes. Human systemic effects: ataxia, blood pressure elevation, change in heart rate, changes in tubules, convulsions or effect on seizure threshold, dtarrhea, distorted perceptions, hallucinations, hypermotility, muscle contraction, musculoskeletal tumors, nausea or vomiting, toxic psychosis, tremors. A human teratogen causing developmental abnormalities of the craniofacial and musculoskeletal systems, pregnancy termination (abortion), and stillbirth. Human maternal effects include an unspecified effect on labor or chddbirth. Human mutation data reported. An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental carcinogenic data. Large doses (above 1.0 g> cause palpitation, excitement, insomnia, dtzziness, headache, and vomiting. Continued excessive use of caffeine in tea or coffee may lead to digestive disturbances, constipation, palpitations, shortness of breath, and depressed mental states. It is also implicated in cardiac disorders under those condttions. When heated to decomposition it emits toxic fumes of NOx
Synthesis
Usually obtained from tea dust in which it is present up to 5% or as a by-product from the manufacture of caffeine-free coffee; synthetically prepared starting with dimethylurea and malonic acid.
Environmental Fate
Caffeine can have profound effects on the cardiovascular
system. At least four mechanisms have been proposed for the
pro-arrhythmic potential of caffeine in overdose. First,
caffeine increases circulating catecholamines. Second, caffeine
inhibits phosphodiesterase. Increased circulating catecholamines
after caffeine overdose increase b1-receptor stimulation.
Stimulation of b1-receptors increases intracellular cAMP
by G protein stimulation of adenylate cyclase. The activity of
cAMP is prolonged due to its decreased metabolism as
phosphodiesterase is inhibited by caffeine. Subsequently,
b1-receptor effects are exaggerated and tachydysrhythmias are
induced. Third, caffeine increases myocardial intracellular calcium. Caffeine both induces release of calcium from the
sarcoplasmic reticulumand blocks calcium’s reuptake into the
sarcoplasmic reticulum. This resulting increase in cytosolic
calcium may provoke dysrhythmias. Fourth, caffeine blocks
cardiac adenosine receptors, which have been shown to be
antiarrhythmic.
The hypotension that has been noted with overdoses of
caffeine is due primarily to two mechanisms. First, caffeineinduced
tachydysrhythmias lead to inadequate filling of the
heart and subsequent decrease in cardiac output. Second,
caffeine augments β2-effects and causes subsequent vasodilation
with resulting hypotension.
Metabolism
Caffeine metabolism occurs mainly in the liver via the cytochrome CYP1A2 enzyme. The products of caffeine metabolism include paraxanthine, theobromine, and theophylline. The first step of caffeine metabolism is demethylation, yielding paraxanthine (a major metabolite), followed by theobromine, and theophylline, which are both minor metabolites. They are then excreted in urine as urates after additional metabolism. The enzymes xanthine oxidase and N-acetyltransferase 2 (NAT2) also participate in the metabolism of caffeine.
storage
-20°C
Purification Methods
Caffeine crystallises from water or absolute EtOH. [Beilstein 26 III/IV 2338.]
Toxicity evaluation
Caffeine’s production and widespread use as an additive to food and as a stimulant may result in release to the environment through waste systems. It has an estimated vapor pressure of 7.3×10-9 mmHg (25°C), which indicates that it will exist as particulate in the atmosphere. Caffeine is not susceptible to photolysis and if released into soil it has a high mobility based on the Koc of 22.
Properties of Caffeine
Melting point: | 234-236.5 °C(lit.) |
Boiling point: | 178°C |
Density | 1.23 |
refractive index | 1.6590 (estimate) |
FEMA | 2224 | CAFFEINE |
Flash point: | 178°C |
storage temp. | 2-8°C |
solubility | Sparingly soluble in water, freely soluble in boiling water, slightly soluble in ethanol (96 per cent). It dissolves in concentrated solutions of alkali benzoates or salicylates. |
pka | pKa 0.6 (Uncertain) |
form | Crystals or Crystalline Powder |
color | Silky white or white |
PH | pH (10g/l, 25℃) : 5.5~6.5 |
Odor | at 100.00 %. odorless |
Water Solubility | 20 g/L (20 ºC) |
Merck | 14,1636 |
Sublimation | 178 ºC |
BRN | 17705 |
Stability: | Stable. Incompatible with strong acids, strong bases, strong oxidizing agents, iodine, silver salts, tannins. Weakly light sensitive in solution. |
CAS DataBase Reference | 58-08-2(CAS DataBase Reference) |
NIST Chemistry Reference | Caffeine(58-08-2) |
IARC | 3 (Vol. 51) 1991 |
EPA Substance Registry System | Caffeine (58-08-2) |
Safety information for Caffeine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Computed Descriptors for Caffeine
New Products
Bromine 99.5% AR (4 x 500ml) Fehling's Solution No. B Amino Acid Kit of 23 items set Ammonium Molybdate Reagent Solution Beam's Reagent Solution Ehrlich's Reagent For detection of urobillinogen Sodium Amino Salicylate Dihydrate (PAS Sodium) IP/BP/USP/EP 1,2,3,4-Tetrahydrocarbazol-4-one 4-Hydroxy Carbazole Amino Salicylic Acid. U.S.P. 2 – Methoxy – 5- Sulfamoyl Benzoic acid Acetone Isobutryl oxime ester Curcuma aromatica Oil Curry leaf Extract Terminalia bellirica Extract Aloe vera extract 200x Withania somnifera (Ashwagandha Extract) Citrus bioflavonoids Extract Ethyl 3-(Pyridin-2-Ylamino)Propanoate Bilastine -IP/BP/ Cypermethric Acid Chloride 5-Nitrosalicylaldehyde 5-(Difluoromethoxy)-2-Mercapto-1H-Benzimidazole- IP/BP/ Methyl Di Chloride (Mdc)Related products of tetrahydrofuran
You may like
-
Caffeine CAS 58-08-2View Details
58-08-2 -
Caffeine CAS 58-08-2View Details
58-08-2 -
Caffeine CAS 58-08-2View Details
58-08-2 -
Caffeine Anhydrous ExiPlus CAS 58-08-2View Details
58-08-2 -
Caffeine, GR 99%+ CAS 58-08-2View Details
58-08-2 -
Caffeine, 98% CAS 58-08-2View Details
58-08-2 -
CAFFEINE CASView Details
-
Caffeine 99.00% CAS 58-08-2View Details
58-08-2