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キニン

キニン 化学構造式
130-95-0
CAS番号.
130-95-0
化学名:
キニン
别名:
キニン;(8S,9R)-6'-メトキシシンコナン-9-オール;(8α,9R)-6'-メトキシシンコナン-9-オール;キニーネ;(8S,9R)-6'-メトキシ-9-ヒドロキシシンコナン;9-epi-キニジン;(8S,9R)-キニン;[(8α,9R)-6'-メトキシシンコナン-9-オール];(-)-キニン;キニーネ(キニン)
英語化学名:
Quinine
英語别名:
Kinin;Quinie;Chinin;Quinina;chinine;QUININE;NSC 192949;Kinidin-d3;Pitayin-d3;(-)-QUININE
CBNumber:
CB9720330
化学式:
C20H24N2O2
分子量:
324.42
MOL File:
130-95-0.mol

キニン 物理性質

融点 :
173-175 °C(lit.)
比旋光度 :
-172 º (c=1, EtOH)
沸点 :
462.75°C (rough estimate)
比重(密度) :
1.1294 (rough estimate)
屈折率 :
1.6250 (estimate)
貯蔵温度 :
Refrigerator
溶解性:
H2O: soluble
外見 :
Crystalline Powder
酸解離定数(Pka):
8.52(at 25℃)
色:
White
酸塩基指示薬変色域(pH):
Blue I uorescence (3.0) to weak violet I uorescence (5.0);Weak violet I uorescence (9.5) to nonI uorescence (10.0)
PH:
9.0 (0.5g/l, H2O, 20℃)
光学活性 (optical activity):
[α]25/D 165°, c = 2 in ethanol
水溶解度 :
slightly soluble
Sensitive :
Light Sensitive
Merck :
14,8061
BRN :
91867
主な用途:
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 データベース:
130-95-0(CAS DataBase Reference)
NISTの化学物質情報:
Quinine(130-95-0)
EPAの化学物質情報:
Cinchonan-9-ol, 6'-methoxy-, (8.alpha.,9R)-(130-95-0)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn,Xi
Rフレーズ  36/37/38-42/43-22-20/22-20/21/22-36/38
Sフレーズ  22-26-36/37-45-37/39-36-7
RIDADR  1544
WGK Germany  3
RTECS 番号 VA6020000
8
国連危険物分類  6.1(b)
容器等級  III
HSコード  29392110
有毒物質データの 130-95-0(Hazardous Substances Data)
化審法 (9)-322
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H317 アレルギー性皮膚反応を起こすおそれ 感作性、皮膚 1 警告 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
H334 吸入するとアレルギー、喘息または、呼吸困難 を起こすおそれ 感作性、呼吸器 1 危険 P261, P285, P304+P341, P342+P311,P501
H335 呼吸器への刺激のおそれ 特定標的臓器毒性、単回暴露; 気道刺激性 3 警告
注意書き
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P284 呼吸用保護具を着用すること。
P304+P340 吸入した場合:空気の新鮮な場所に移し、呼吸しやすい 姿勢で休息させること。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P342+P311 呼吸に関する症状が出た場合:医師に連絡すること。
P405 施錠して保管すること。

キニン 価格 もっと(24)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBOR-4054 キニン
Quinine
130-95-0 1g ¥3600 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00017183 キニン
Quinine
130-95-0 1g ¥10100 2018-12-26 購入
東京化成工業 Q0028 キニン >98.0%(T)
Quinine >98.0%(T)
130-95-0 25g ¥10800 2018-12-04 購入
東京化成工業 Q0028 キニン >98.0%(T)
Quinine >98.0%(T)
130-95-0 100g ¥32800 2018-12-04 購入
関東化学株式会社(KANTO) 16370-1A キニーネ(キニン)
Quinine, anhydrous
130-95-0 10g ¥10300 2018-12-13 購入

キニン MSDS


Quinine

キニン 化学特性,用途語,生産方法

外観

白色~わずかにうすい黄色、結晶~粉末又は塊

溶解性

エタノール(99.5)に溶け、水にほとんど溶けない。

用途

抗マラリア剤として作用しま す。

用途

抗マラリア剤として作用しま す。

用途

キニーネ(蘭: kinine)またはキニン(英: quinine)マラリア原虫に特異的に毒性を示すマラリアの特効薬である。 その後、キニーネの構造を元にクロロキンやメフロキンなどの人工的な抗マラリア薬が開発され、ある程度の副作用のあるキニーネは代替されてあまり用いられなくなっていった。
キニーネ自身の水溶性は低いため、塩酸キニーネや硫酸キニーネといった塩の形で投与される。キニーネはマラリア原虫に特異的に毒性を示す。マラリア原虫は赤血球中でヘモグロビンを取り込み栄養源として利用している。しかしヘモグロビンの代謝の際に原虫にとって有毒なヘムが生成する。原虫はこのヘムをヘムポリメラーゼによって重合させて無毒化している。キニーネはこのヘムポリメラーゼを阻害することによって原虫に対して毒性を発揮するという説が有力である。
キニーネは食品添加物として認可されており、トニックウォーターに苦味剤として添加される。また強い苦味を持つ物質として知られている。そのため、トニックウォーターに苦味剤として添加される。
有機化学分野では光学分割剤として用いられる。ラセミ体の酸をキニーネ塩にしてジアステレオマーとし、分離する方法で用いられる。

用途

抗マラリア、薬苦味剤、有機合成。

用途

分析用試薬 : 1) ビスマス、白金などの検出。2) ゲルマニウムの検出。3) セリウムの検出。4) 硫酸イオンの検出。5) タングステンの定量。6) リン酸イオンの検出、比色分析。

効能

抗マラリア薬

化学的特性

white to light yellow crystal powde

化学的特性

Quinine is odorless, but has an intense, bitter taste

天然物の起源

Reported present in Cinchona officinalis.

来歴

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).

使用

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.

使用

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.

使用

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

使用

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

使用

antimalarial, skeletal muscle relaxant

使用

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.

定義

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

製造方法

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

適応症

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.

定義

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

定義

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.

抗菌性

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.

獲得抵抗性

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.

危険性

Skin irritant, ingestion of pure substance adversely affects eyes.

健康ハザード

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.

応用例(製薬)

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.

薬物動態学

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.

臨床応用

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.

副作用

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.

副作用

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.

安全性プロファイル

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.

純化方法

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.]

キニン 上流と下流の製品情報

原材料

準備製品


キニン 生産企業

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130-95-0(キニン)キーワード:


  • 130-95-0
  • Quinie
  • Quinine, anhydrous, 99%(total base), may cont. up to 5% dihydroquinine
  • Basic Quinine Hydrochloride
  • Chininii Chloridum
  • Kinin
  • Quinina
  • Quininium Chloride
  • Cinchonan-9-ol, 6'-methoxy-, (8α,9R)-
  • (8a,9R)-6’-Methoxycinchonan-9-ol
  • Quinine, 99%, anhydrous
  • (8α,9R)-6'-Methoxycinchonan-9-ol
  • Quinine ,97% [anhydrous]
  • (R)-[(2S,4S,5R)-5-Vinyl-1-azabicyclo[2.2.2]oct-2-yl](6-methoxyquinolin-4-yl)methanol
  • quinine( (8α,9R)-6'-methoxy-Cinchonan-9-ol )
  • (8-alpha,9r)-6’-methoxycinchonan-9-ol
  • (1R)-(6-methoxyquinolin-4-yl)((2S)-5-vinylquinuclidin-2-yl)methanol
  • (R)-(6-Methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol
  • Quinine,99%d.e.
  • (-)-Quinine for resolution of racemates for synthesis
  • Quinine, (R)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol
  • Quinine, Anhydrous, may cont. up to 5% dihydroquinine
  • 6’-methoxy-,(8alpha,9r)-cinchonan-9-o
  • 6’-methoxy-,(8alpha,9theta)-cinchonan-9-o
  • 6'-Methoxycinchonidine
  • alpha-(6-methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethano
  • alpha-(6-Methoxy-4-quinoyl)-5-vinyl-2-quinclidinemethanol
  • Chinin
  • chinine
  • Cinchonan-9-ol, 6'-methoxy-, (8a,9R)-
  • Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-
  • キニン
  • (8S,9R)-6'-メトキシシンコナン-9-オール
  • (8α,9R)-6'-メトキシシンコナン-9-オール
  • キニーネ
  • (8S,9R)-6'-メトキシ-9-ヒドロキシシンコナン
  • 9-epi-キニジン
  • (8S,9R)-キニン
  • [(8α,9R)-6'-メトキシシンコナン-9-オール]
  • (-)-キニン
  • キニーネ(キニン)
  • キノリン
  • キノリンアルカロイド
  • その他 (試験研究用抗生物質)
  • 不斉有機触媒
  • 構造分類
  • 光学分割
  • 抗生物質
  • 生化学
  • 試験研究用抗菌剤
  • 酸の光学分割剤
  • 有機合成化学
  • アルカロイド
  • アルコキシキノリン
  • キナ·アルカロイド
  • 骨格筋作用薬
  • 抗マラリア薬
  • 鎮痛薬
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