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퀴닌

퀴닌
퀴닌 구조식 이미지
카스 번호:
130-95-0
한글명:
퀴닌
동의어(한글):
퀴닌;퀴닌및그염류
상품명:
Quinine
동의어(영문):
Kinin;Quinie;Chinin;Quinina;chinine;QUININE;NSC 192949;Kinidin-d3;Pitayin-d3;(-)-QUININE
CBNumber:
CB9720330
분자식:
C20H24N2O2
포뮬러 무게:
324.42
MOL 파일:
130-95-0.mol

퀴닌 속성

녹는점
173-175 °C(lit.)
알파
-172 º (c=1, EtOH)
끓는 점
462.75°C (rough estimate)
밀도
1.1294 (rough estimate)
굴절률
1.6250 (estimate)
저장 조건
Refrigerator
용해도
H2O: soluble
물리적 상태
Crystalline Powder
산도 계수 (pKa)
8.52(at 25℃)
색상
White
pH 범위
Blue I uorescence (3.0) to weak violet I uorescence (5.0);Weak violet I uorescence (9.5) to nonI uorescence (10.0)
수소이온지수(pH)
9.0 (0.5g/l, H2O, 20℃)
optical activity
[α]25/D 165°, c = 2 in ethanol
수용성
slightly soluble
감도
Light Sensitive
Merck
14,8061
BRN
91867
주요 응용
Bird repellents, sunscreen, antimalarial agent, antiviral agent, antitumor agent, drug-coated coronaryagent, antiparasitic agent, treatment of epilepsy, skeletal muscle spasm, drug-coated coronary stent system
CAS 데이터베이스
130-95-0(CAS DataBase Reference)
NIST
Quinine(130-95-0)
EPA
Cinchonan-9-ol, 6'-methoxy-, (8.alpha.,9R)-(130-95-0)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,Xi
위험 카페고리 넘버 36/37/38-42/43-22-20/22-20/21/22-36/38
안전지침서 22-26-36/37-45-37/39-36-7
유엔번호(UN No.) 1544
WGK 독일 3
RTECS 번호 VA6020000
F 고인화성물질 8
위험 등급 6.1(b)
포장분류 III
HS 번호 29392110
유해 물질 데이터 130-95-0(Hazardous Substances Data)
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H334 흡입 시 알레르기성 반응, 천식 또는 호흡 곤란 등을 일으킬 수 있음 호흡기 과민성 물질 구분 1 위험 P261, P285, P304+P341, P342+P311,P501
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P284 호흡 보호구를 착용하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P342+P311 호흡기 증상이 나타나면 의료기관(의사)의 진찰을 받으시오.
P405 밀봉하여 저장하시오.

퀴닌 MSDS


Quinine

퀴닌 C화학적 특성, 용도, 생산

물성

Quinine은 항 말라리아제입니다. Quinine은 DNA 복제를 억제하여 적혈구 형태의 다이아몬드와 말라리아의 분열을 억제합니다. Quinine은 또한 국소 마취와 자극 효과가 있습니다. Quinine은 체온 조절의 중심을 억제 할 수 있고, 높은 복용량을 사용할 때 대뇌 피질의 시각 및 청각 영역의 작용을 억제 할 수 있습니다. Quinine은 불응 기간을 연장시키고 심장 근육의 수축성과 흥분성을 낮 춥니 다. 퀴닌 (Quinine)은 내부 장기의 평활근 세포를 자극하고 리듬 성 수축을 촉진하며 자궁의 색조를 증가시킵니다.

개요

퀴닌(quinine)은 해열·진통·말라리아 예방 등의 효과가 있는 알칼로이드이다.알칼로이드계 화합물의 일종. 기나나무속(Quinine tree)의 나무껍질에서 추출해 낸다. 우리나라에서는 철자 그대로 읽어서 키니네라고도 불렀으며, 말라리아 치료제로 널리 쓰였다.

화학적 성질

white to light yellow crystal powde

화학적 성질

Quinine is odorless, but has an intense, bitter taste

출처

Reported present in Cinchona officinalis.

역사

Quinine is a white crystalline alkaloid best known for treating malaria. Quinine is derived from the bark of several species of trees in the genus Cinchona in the Rubiaceae family. Cinchona trees grow on the eastern slopes of the Andes Mountains at elevations of several thousand feet. Because these symptoms were associated with malaria, Cinchona bark powder was recognized as a possible treatment in the 1600s by Jesuit missionaries.
After decades of work by numerous investigators, quinine was finally isolated in 1820 by Pierre-Joseph Pelletier (1788–1842) and Joseph-Bienaimé Caventou (1795–1877). The name quinine originates from the native word for the Cinchona tree quina quina, which became the Spanish word quino for cinchona. The development of organic synthesis in the middle of the 19th century and the limited supply of quinine stimulated attempts to synthesize it. William Henry Perkins’s (1838–1907) attempt to synthesize quinine in 1856 led to his discovery of mauve, which was a signifi cant discovery in the dye industry (see Indigo).

용도

Quinines use as an antimalarial agent spans several hundred years, but it has been replaced in recent years by other substances such as chloroquine. Because some Plasmodium strains have developed resistance to several malaria medications, quinine use is being revived. About 60% of quinine production is used for medicinal purposes, and the drug is available by prescription. In addition to its use as an antimalarial agent, quinine medications are used to treat leg cramps, muscle cramps associated with kidney failure, hemorrhoids, heart palpitations, and as an analgesic. At higher concentrations it is toxic and causes a condition known as cinchonism. Conditions associated with cinchonism include dizziness, hearing loss, visual impairment, nausea, and vomiting.
Nonmedicinal use of quinine, accounting for about 40% of its use, is primarily as a fl avoringagent in condiments and liqueurs. The most common food use of quinine is tonic water. Tonicwater originated in India where English colonists drank carbonated water mixed with quinineto prevent malaria. The bitter taste of quinine was often masked by mixing it with alcoholicbeverages; one result of this practice was the drink gin and tonic. Current Food and DrugAdministration regulations in the United States limit the amount of quinine in tonic water to83 parts per million (83 mg per liter). This level is signifi cantly less than that required for therapeuticpurposes, so the use of commercial tonic waters to combat malaria is not practical.

용도

Primary alkaloid of various species of Cinchona (Rubiaceae). Optical isomer of Quinidine. Antimalarial; muscle relaxant (skeletal)

용도

Because of its relatively constant and well-known fluorescence quantum yield, quinine is also used in photochemistry as a common fluorescence standard. It has been used for imaging of oxygen evolution and oxide formation. Chloride and bromide have been sh

용도

antimalarial, skeletal muscle relaxant

용도

Quinine is a flavorant naturally obtained from the cinchona tree. it is used as a bitter flavoring in beverages such as quinine water, tonic water, and bitter lemon. quinine sulfate and quinine hydrochloride are cleared for use as a flavor in carbonated beverages at levels less than 83 ppm.

용도

Quinine occurs in the dried stems or rootbarks of cinchona (Cinchona ledgerianaMoens). It is used in the treatment of malaria.It is also used as an analgesic and antipyreticagent.

정의

A poisonous ALKALOID found in the bark of the cinchona tree of South America. It is used in treating malaria.

정의

quinine: A white solid,C20H24N2O2·3H2O, m.p. 57°C. It is apoisonous alkaloid occurring in thebark of the South American cinchonatree, although it is now usually producedsynthetically. It forms saltsand is toxic to the malarial parasite,and so quinine and its salts are used to treat malaria; in small doses itmay be prescribed for colds and influenza.In dilute solutions it has apleasant astringent taste and is addedto some types of tonic water.

정의

ChEBI: A cinchona alkaloid that is cinchonidine in which the hydrogen at the 6-position of the quinoline ring is substituted by methoxy.

Indications

Quinine is one of several alkaloids derived from the bark of the cinchona tree. The mechanism by which it exerts its antimalarial activity is not known. It does not bind to DNA at antimalarial dosages. It may poison the parasite’s feeding mechanism, and it has been termed a general protoplasmic poison, since many organisms are affected by it.
Quinine is rapidly absorbed following oral ingestion, with peak blood levels achieved in 1 to 4 hours. About 70 to 93% of the drug is bound to plasma proteins, depending on the severity of the infection. Quinine is extensively metabolized, with only about 20% of the parent compound eliminated in the urine.
The primary present-day indication for quinine and its isomer, quinidine, is in the intravenous treatment of severe manifestations and complications of chloroquine- resistant malaria caused by P. falciparum.
Aside from its use as an antimalarial compound, quinine is used for the prevention and treatment of nocturnal leg muscle cramps, especially those resulting from arthritis, diabetes, thrombophlebitis, arteriosclerosis, and varicose veins.

제조 방법

By reaction from cinchona bark (Cinchona officinalis), where it is present at approximately 8%.

Antimicrobial activity

Quinine inhibits the erythrocytic stages of human malaria parasites at <1 mg/L, but not the liver stages. It is active against the gametocytes of P. vivax, P. ovale and P. malariae, but not P. falciparum. The dextrarotatory stereoisomer, quinidine, is more active than quinine, but epiquinine (cinchonine) and epiquinidine (cinchonidine) have much lower antimalarial activities.

원료

Resistance is now widespread in South East Asia, where some strains are also resistant to chloroquine, sulfadoxine– pyrimethamine and mefloquine. Cross-resistance with mefloquine has been demonstrated in P. falciparum, but genetic polymorphisms associated with chloroquine resistance are not associated with quinine resistance.

위험도

Skin irritant, ingestion of pure substance adversely affects eyes.

건강위험

The toxicity of quinine is characterized bycinchonism, a term that includes tinnitus,vomiting, diarrhea, fever, and respiratorydepression. Other effects include stimulationof uterine muscle, analgesic effect,and dilation of the pupils. Severe poisoningmay produce neurosensory disorders, causingclouded vision, double vision, buzzing of theears, headache, excitability, and sometimescoma (Ferry and Vigneau 1983). Death fromquinine poisoning is unusual. Massive dosesmay be fatal, however.
LD50 value, oral (guinea pigs): 1800 mg/kg.

Pharmaceutical Applications

A quinolinemethanol from the bark of the Cinchona tree; the laevorotatory stereoisomer of quinidine. Formulated as the sulfate, bisulfate or ethylcarbonate for oral use and as the dihydrochloride for parenteral administration. The salts are highly soluble in water.

Pharmacokinetics

Oral absorption: 80–90%
Cmax 600 mg oral: 5 mg/L after 1–3 h
Plasma half-life: 8.7 h
Volume of distribution: 1.8 L/kg
Plasma protein binding: c. 70%
Quinine is well absorbed by the oral route. Intramuscular administration gives more predictable data than intravenous administration and may be more useful in children. Plasma protein binding rises to 90% in uncomplicated malaria and 92% in cerebral malaria due to high levels of acute-phase proteins. Similarly, the elimination half-life rises to 18.2 h in severe malaria. There is extensive hepatic metabolism to hydroxylated derivatives. Urinary clearance is <20% of total clearance.

Clinical Use

Falciparum malaria (alone or in combination with tetracycline, doxycycline, clindamycin or pyrimethamine–sulfadoxine)
Babesiosis (in combination with clindamycin)
It is particularly used in cerebral malaria if chloroquine resistance is suspected (Ch. 62). It is not recommended for treatment of uncomplicated falciparum malaria.

부작용

Up to 25% of patients experience cardiac dysrhythmia, hypoglycemia, cinchonism (tinnitus, vomiting, diarrhea, headache). Severe effects, including hypotension and hypoglycemia, are of particular importance in children, pregnant women and the severely ill. Rarely, it can induce hemolytic anemia (‘blackwater fever’). Quinine inhibits tryptophan uptake into cells.

부작용

Cinchonism describes the toxic state induced by excessive plasma levels of free quinine. Symptoms include sweating, ringing in the ears, impaired hearing, blurred vision, nausea, vomiting, and diarrhea. Quinine is a potent stimulus to insulin secretion and irritates the gastrointestinal mucosa. Also, a variety of relatively rare hematological changes occur, including leukopenia and agranulocytosis. Quinine is potentially neurotoxic in high dosages, and severe hypotension may follow its rapid intravenous administration.

Safety Profile

Human poison by unspecified route. Experimental poison by subcutaneous, intravenous, intramuscular, and intraperitoneal routes. Moderately toxic experimentally by ingestion. An experimental teratogen. Human systemic effects by ingestion: visual field changes, tinnitus, and nausea or vomiting. Human teratogenic effects by ingestion: developmental abnormahties of the central nervous system, body wall, and musculoskeletal, cardovascular, and hepatoblltary systems. Experimental reproductive effects. Mutation data reported. Can cause temporary loss of vision. Quinine dermatitis is an occupational hazard to barbers particularly, and generally to people who work with quinine tonics, medcaments, or cosmetics. An irritant to mucous membranes. Combustible when exposed to heat or flame. Decomposes on exposure to light. When heated to decomposition it emits toxic fumes of NOx. Used to treat malaria.

Purification Methods

Crystallise the quinine from absolute EtOH. It has been used as a chiral catalyst (see previous entry). [Beilstein 23 H 511, 23 I 166, 23 II 416, 23 III/IV 3265, 23/13 V 395.]

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