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キニジン

キニジン 化学構造式
56-54-2
CAS番号.
56-54-2
化学名:
キニジン
别名:
キニジン;キニジン硫酸銅溶液 (スプレー用);(+)-(3R,4S,8R,9S)-キニジン;(8R,9S)-キニジン;キニジンピバラート;ピタイイン;(9S)-6'-メトキシシンコナン-9-オール;(8R,9S)-6'-メトキシシンコナン-9-オール;β-キニン;コンキニン;(+)-キニジン;キニジン硫酸銅溶液 [スプレー用];キニジン(無水)
英語化学名:
Quinidine
英語别名:
Kinidin;Pitayin;PITAYINE;QUINDINE;QUNIDINE;Chinidin;Cin-quin;Quinidex;QUINIDINE;B-QUININE
CBNumber:
CB9208047
化学式:
C20H24N2O2
分子量:
324.42
MOL File:
56-54-2.mol

キニジン 物理性質

融点 :
168-172 °C(lit.)
比旋光度 :
256 º (c=1, EtOH)
沸点 :
462.75°C (rough estimate)
比重(密度) :
1.1294 (rough estimate)
屈折率 :
1.5700 (estimate)
貯蔵温度 :
Store at -20°C
外見 :
Powder
酸解離定数(Pka):
5.4, 10.0(at 20℃)
色:
White to off-white
光学活性 (optical activity):
[α]20/D +265±5°, c = 0.8% in ethanol (dry matter)
水溶解度 :
0.05 g/100 mL (20 ºC)
Sensitive :
Light Sensitive
Merck :
14,8060
BRN :
91866
安定性::
Stable. Incompatible with strong oxidizing agents.
CAS データベース:
56-54-2(CAS DataBase Reference)
NISTの化学物質情報:
Quinine(56-54-2)
EPAの化学物質情報:
Quinidine (56-54-2)
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
Rフレーズ  22-20/21/22
Sフレーズ  36-22
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS 番号 VA4725000
8
TSCA  Yes
国連危険物分類  6.1(b)
容器等級  III
HSコード  29392000
有毒物質データの 56-54-2(Hazardous Substances Data)
毒性 LD50 in rats (mg/kg): 30 i.v., 263 orally (Dietmann)
化審法 (9)-324
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
H301 飲み込むと有毒 急性毒性、経口 3 危険 P264, P270, P301+P310, P321, P330,P405, P501
注意書き
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時に、飲食または喫煙をしないこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P321 特別な処置が必要である(このラベルの... を見よ)。
P405 施錠して保管すること。

キニジン 価格 もっと(20)

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-3804 キニジン
Quinidine
56-54-2 1g ¥3600 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00017180 キニジン
Quinidine
56-54-2 1g ¥10100 2018-12-26 購入
東京化成工業 Q0006 キニジン >85.0%(HPLC)
Quinidine >85.0%(HPLC)
56-54-2 25g ¥19000 2018-12-04 購入
東京化成工業 Q0006 キニジン >85.0%(HPLC)
Quinidine >85.0%(HPLC)
56-54-2 5g ¥6400 2018-12-04 購入
関東化学株式会社(KANTO) 16368-2A キニジン(無水)
Quinidine, anhydrous
56-54-2 25g ¥22900 2018-12-13 購入

キニジン 化学特性,用途語,生産方法

外観

白色~ほとんど白色, 結晶~粉末

溶解性

溶媒 : アルコール, エーテル, クロロホルムエタノール(99.5)に溶ける。

用途

薬理研究用試薬、光学分割剤。

効能

抗不整脈薬, 抗マラリア薬, ナトリウムチャネル遮断薬

説明

Quinidine is a commonly used class I antiarrhythmic drug. It is a stereoisomer of quinine, originally derived from the bark of the cinchona tree. It exerts its antiarrhythmic effects on the heart by interacting with the electrophysiology mechanisms that cause arrhythmias to modify the abnormalities in impulse initiation and conduction. Quinidine depresses normal automaticity in cardiac fibers that may act as ectopic pacemakers causing arrhythmias. Quinidine also blocks the slowly inactivating, tetrodotoxin-sensitive Na current, the slow inward calcium current (ICa), the rapid (IKr) and slow (IKs) components of the delayed potassium rectifier current, the inward potassium rectifier current (IKI), the ATP-sensitive potassium channel (IKATP) and Ito.

化学的特性

white to light yellow crystal powde

使用

A dextrorotatory stereoisomer of Quinine. Antiarrhythmic (class IA). Antimalarial

使用

antiarrhythmic, antimalarial

使用

Quinidine occurs in cinchona bark to about0.25–0.3% and also in cuprea bark. It is present in quinine sulfate mother liquor. Itis formed by isomerization of quinine. Itis used in the prevention of certain cardiacarrhythmias.

定義

ChEBI: A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.

brand name

Duraquin (Warner Chilcott); Quinaglute (Berlex).

生物学の機能

Quinidine is an alkaloid obtained from various species of Cinchona or its hybrids, from Remijia pedunculata, or from quinine. Quinidine is the dextrorotatory isomer of quinine.Quinidine (Quinidex) was one of the first clinically used antiarrhythmic agents. Because of the high incidence of ventricular proarrhythmia associated with its use and numerous other equally efficacious agents, quinidine is now used sparingly. Quinidine shares all of the pharmacological properties of quinine, including antimalarial, antipyretic, oxytocic, and skeletal muscle relaxant actions.

一般的な説明

Crystals or white powder.

空気と水の反応

Insoluble in water.

危険性

Poison.

健康ハザード

Quinidine is more potent than quinine in itsaction on the cardiovascular system. Overdosesmay cause lowering of blood pressure.Gastric effects are lower than quinine. Toxicityis lower relative to quinine; subcutaneouslethal dose in mice is 400 mg/kg against200 mg/kg for quinine.

火災危険

Flash point data for Quinidine are not available. Quinidine is probably combustible.

臨床応用

Primary indications for the use of quinidine include (1) abolition of premature complexes that have an atrial, A-V junctional, or ventricular origin; (2) restoration of normal sinus rhythm in atrial flutter and atrial fibrillation after controlling the ventricular rate with digitalis; (3) maintenance of normal sinus rhythm after electrical conversion of atrial arrhythmias; (4) prophylaxis against arrhythmias associated with electrical countershock; (5) termination of ventricular tachycardia; and (6) suppression of repetitive tachycardia associated with Wolff- Parkinson-White (WPW) syndrome.
Although quinidine often is successful in producing normal sinus rhythm, its administration in the presence of a rapid atrial rate (flutter and possibly atrial fibrillation) can lead to a further and dangerous increase in the ventricular rate secondary to inhibition of basal vagal tone upon the A-V node. For this reason, digitalis should be used before quinidine when one is attempting to convert atrial flutter or atrial fibrillation to normal sinus rhythm.

副作用

The most common adverse effects associated with quinidine administration are diarrhea (35%), upper gastrointestinal distress (25%), and light-headedness (15%). Other relatively common adverse effects include fatigue, palpitations, headache (each occurring with an incidence of 7%), anginalike pain, and rash. These adverse effects are generally dose related and reversible with cessation of therapy. In some patients, quinidine administration may bring on thrombocytopenia due to the formation of a plasma protein–quinidine complex that evokes a circulating antibody directed against the blood platelet. Although platelet counts return to normal on cessation of therapy, administration of quinidine or quinine at a later date can cause the reappearance of thrombocytopenia.
The cardiac toxicity of quinidine includes A-V and intraventricular block, ventricular tachyarrhythmias, and depression of myocardial contractility. Ventricular arrhythmia induced by quinidine leading to a loss of consciousness has been referred to as quinidine syncope. This devastating side effect is more common in women than in men and may occur at therapeutic or subtherapeutic plasma concentrations. Large doses of quinidine can produce a syndrome known as cinchonism, which is characterized by ringing in the ears, headache, nausea, visual disturbances or blurred vision, disturbed auditory acuity, and vertigo. Larger doses can produce confusion, delirium, hallucinations, or psychoses.Quinidine can decrease blood glucose concentrations, possibly by inducing insulin secretion.

安全性プロファイル

Poison by ingestion, subcutaneous, intravenous, intramuscular, and intraperitoneal routes. A skin irritant. Implicated in aplastic anemia. When heated to decomposition it emits toxic fumes of NOx.

薬物相互作用

Quinidine can increase the plasma concentrations of digoxin, which may in turn lead to signs and symptoms of digitalis toxicity. Gastrointestinal, central nervous system (CNS), or cardiac toxicity associated with elevated digoxin concentrations may occur.Quinidine and digoxin can be administered concurrently; however, a downward adjustment in the digoxin dose may be required.
Drugs that have been associated with elevations in quinidine concentrations include acetazolamide, the antacids magnesium hydroxide and calcium carbonate, and the H2-receptor antagonist cimetidine. Cimetidine inhibits the hepatic metabolism of quinidine. Phenytoin, rifampin, and barbiturates increase the hepatic metabolism of quinidine and reduce its plasma concentrations.

純化方法

Crystallise it from *C6H6 or dry CHCl3/pet ether (b 40-60o), discarding the initial, oily crop of crystals. Dry it under vacuum at 100o over P2O5. It has been used as a chiral catalyst [Wynberg & Staring J Am Chem Soc 104 166 1982, J Org Chem 50 1977 1985]. [Beilstein 23 H 506, 23 I 164, 23 II 414, 23 III/IV 3261, 23/13 V 395.]

予防処置

One of the few absolute contraindications for quinidine is complete A-V block with an A-V pacemaker or idioventricular pacemaker; this may be suppressed by quinidine, leading to cardiac arrest.
Persons with congenital QT prolongation may develop torsades de pointes tachyarrhythmia and should not be exposed to quinidine.
Owing to the negative inotropic action of quinidine, it is contraindicated in congestive heart failure and hypotension. Digitalis intoxication and hyperkalemia can accentuate the depression of conduction caused by quinidine.
Myasthenia gravis can be aggravated severely by quinidine’s actions at the neuromuscular junction. The use of quinidine and quinine should be avoided in patients who previously showed evidence of quinidine- induced thrombocytopenia.

参考文献

Wit, Andrew L. "The Effects of Quinidine on the Cellular Electrophysiology of the Heart: A Brief Review." Journal of Cardiovascular Electrophysiology 3.5(2010):316-322.
Alloway, J. A., and M. P. Salata. "Quinidine-induced rheumatic syndromes. " Seminars in Arthritis & Rheumatism 24.5(1995):315-322.
Nakano, J, and M. C. R. Jr. "Effect of quinidine on cardiovascular dynamics." Arch Int Pharmacodyn Ther 168.2(1967):400-416.

キニジン 上流と下流の製品情報

原材料

準備製品


キニジン 生産企業

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56-54-2(キニジン)キーワード:


  • 56-54-2
  • (8R,9S)-6'-Methoxycinchonan-9-ol
  • 6-METHOXY-A-(5-VINYL-2-QUINUCLIDINYL)-4-QUINOLINE-METHANOL
  • CONCHININE
  • CONQUININE
  • B-QUININE
  • (+)-QUINIDINE
  • QUINIDINE
  • (+)-QUINDINE
  • QUINDINE
  • PITAYINE
  • Quinidine free base
  • Quinidine anhydrous
  • QUINIDINE, CRYSTALLIZED
  • QUINIDINE FREE BASE ANHYDROUS
  • QUINIDINE, SYNTHESIS GRADE
  • Quinidine, anhydrous, 99+%
  • Quinidine, anhydrous, ca.95%
  • QUNIDINE
  • QUINIDINE(RG)
  • b-Quinidine
  • Cinchonan-9-ol, 6'-methoxy-, (9S)- (9CI)
  • Quinidine,99%d.e.
  • (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
  • (8r,9s)-quinidine
  • (95)-cinchonan-9-0
  • (9s)-6’-methoxycinchonan-9-ol
  • (9S)-6'-Methoxycinchonan-9-ol
  • 2-Quinuclidinemethanol, alpha-(6-methoxy-4-quinolyl)-5-vinyl-
  • 6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol
  • 6'-Methoxycinchonan-9-ol
  • キニジン
  • キニジン硫酸銅溶液 (スプレー用)
  • (+)-(3R,4S,8R,9S)-キニジン
  • (8R,9S)-キニジン
  • キニジンピバラート
  • ピタイイン
  • (9S)-6'-メトキシシンコナン-9-オール
  • (8R,9S)-6'-メトキシシンコナン-9-オール
  • β-キニン
  • コンキニン
  • (+)-キニジン
  • キニジン硫酸銅溶液 [スプレー用]
  • キニジン(無水)
  • キノリン
  • キノリンアルカロイド
  • 不斉合成
  • 不斉有機触媒
  • 構造分類
  • 光学分割
  • 生化学
  • 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
  • αアドレナリン遮断薬
  • 抗不整脈薬
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