카페인

카페인 속성

카페인 C화학적 특성, 용도, 생산

물성

카페인은 쓴맛이 있고 백색 결정성의 퓨린으로 메틸잔틴 알칼로이드이며 화학적으로 DNA와 RNA의 아데닌, 구아닌 염기와 관련이있다. 남미 및 동아시아 고유의 여러 식물의 씨앗, 견과 또는 잎에서 발견되며 곤충으로부터 보호하고 근처의 다른 종자의 발아를 방지하는 역할을 한다.

존재

카페인의 가장 잘 알려진 원료는 커피콩이다. 보통 졸음을 완화 시키거나 예방하고 각성효과를 위해 카페인을 함유한 음료를 섭취한다. 이러한 음료를 만들기 위해 카페인은 물에 식물 제품을 담금작업을 통해 추출된다. 커피, 차, 콜라 같은 카페인 함유 음료는 매우 인기가 있다. 2014년 기준 미국 성인의 85 %는 카페인을 섭취하고 평균 164mg을 섭취한다. 커피 나무, 차, 과라나 열매 등에 존재하며, 카카오 열매와 콜라 열매에도 존재한다. 콜라, 초콜릿 등에도 포함되어 있으며 승화하는 특성이 있다. 이들 식물은 해충을 죽이기 위해 카페인을 사용한다.

개요

카페인(caffeine)은 메틸크산틴 계열의 중추신경계통(CNS) 각성제이다.알칼로이드의 일종이다. 세계에서 가장 널리 사용되는 향정신성 약물이다. 다른 많은 향정신성 물질과는 달리, 거의 모든 세계에서 합법적이며 규제가 없다.

용도

카페인은 건강에 긍정적인 영향과 부정적인 영향을 모두 줄 수 있다. 기관지 형성 장애로 인한 미숙아 호흡장애, 미숙아 무호흡 등을 치료하고 예방할 수 있다. 카페인 구연산염은 WHO의 필수 의약품 모델 목록에 있다.파킨슨 병을 포함한 일부 질병에 대해서는 약간의 보호 효과를 나타낼 수있다.

개요

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.

화학적 성질

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.*

물리적 성질

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.

출처

Reported found in coffee and guarana.

역사

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.

용도

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.

정의

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.

일반 설명

Odorless white powder or white glistening needles, usually melted together. Bitter taste. Solutions in water are neutral to litmus. Odorless.

공기와 물의 반응

Efflorescent in air. Water soluble.

반응 프로필

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.

위험도

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.

건강위험

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.

화재위험

Flash point data for Caffeine are not available; however, Caffeine is probably combustible.

생물학적 활성

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.

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

환경귀착

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.

Purification Methods

Caffeine crystallises from water or absolute EtOH. [Beilstein 26 III/IV 2338.]

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