エフェドリン

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Danger

• 危険有害性情報

  H302：飲み込むと有害

  H314：重篤な皮膚の薬傷?眼の損傷

  H317：アレルギー性皮膚反応を起こすおそれ

• 注意書き

  P260：粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ 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。

  P280：保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。

  P301+P312：飲み込んだ場合：気分が悪い時は医師に連絡する こと。

  P303+P361+P353：皮膚（または髪）に付着した場合：直ちに汚染された衣 類をすべて脱ぐこと/取り除くこと。皮膚を流水/シャワー で洗うこと。

  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。

MSDS Information

• (1R,2S)-(-)-Ephedrine

エフェドリン 化学特性,用途語,生産方法

• 解説

  エフェドリン,無色の結晶．融点38.1 ℃(無水和物)，沸点225 ℃．[α]_D²⁰"－6.3°(エタノール)．水，エタノール，クロロホルムに可溶，石油エーテルに難溶．交感神経末梢を刺激して気管支けいれんを緩解し，瞳孔を拡大する作用がある．この塩酸塩およびN-ジメチル体(メチルエフェドリン)の塩酸塩は，いずれも咳止め薬として用いられている．アドレナリンより薬効は弱いが，持続性がある．
  森北出版「化学辞典（第2版）

• 用途

  医薬、漢方薬の主要アルカロイド

• 作用機序

  エフェドリン,作用機序は，α，β受容体の直接刺激作用，交感神経終末からのカテコールアミン遊離作用，再取込み阻害，MAO (モノアミン酸化酵素) 阻害などが知られており，前の2つが最も重要である。中枢興奮作用，比較的短時間で薬剤耐性を生じること，経口投与可能であることなどは，アドレナリンと大きく異なる点である。

• 製造

  エフェドリン,マオウ科の麻黄Ephedra sinica，E.equisetina，E.distachyaなどに含まれるアルカロイドの一つ．天然には，(1R,2S)-(－)-エフェドリンが見いだされ，ともに含まれる(1R,2R)-(＋)-プソイドエフェドリンとはジアステレオマーの関係にある．1-フェニル-1-プロパノン，ベンズアルデヒドなどを原料とする種々の方法で合成もされている．

• 効能

  気管支拡張薬, アドレナリン受容体作動薬

• 化学的特性

  white crystals or powder

• 使用

  Ephedrine, 1-phenyl-2-methylaminopropanol, C6H5 CH(OH)CH(NHCH3)CH3, is a white-to-colorless granular substance, unctuous (greasy) to the touch, and hygroscopic. The compound gradually decomposes upon exposure to light. Soluble in water, alcohol, ether, chloroform, and oils, and decomposes above this temperature. Ephedrine is isolated from stems or leaves of Ephedra, especially Ma huang (found in China and India). Medically, it is usually offered as the hydrochloride. In the treatment of bronchial asthma, ephedrine is known as a beta agonist. Compounds of this type reduce obstruction by activating the enzyme adenylate cyclase. This increases intracellular concentrations of cAMP (cyclic 3 5 -adenosine monophosphate) in bronchial smooth muscle and mast cells. Ephedrine is most useful for the treatment of mild asthma. In severe asthma, ephedrine rarely maintains completely normal airway dynamics over long periods. Ephedrine also has been used in the treatment of cerebral transient ischemic attacks, particularly with patients with vertabrobasilar artery insufficiency who have symptoms associated with relatively low blood pressure, or with postural changes in blood pressure. Ephedrine sulfate also has been used in drug therapy in connection with urticaria (hives).

• 定義

  ephedrine: An alkaloid,C₆H₅CH(OH)CH(CH₃)NHCH₃ found inplants of the genus Ephedra, onceused as a bronchodilator in the treatmentof asthma. It is also used as astimulant and appetite suppressant.Structurally, it is a phenylethylamineand is similar to amphetamines, althoughless active. It is, however,widely used in the illegal synthesis ofmethamphetamine. The moleculehas two chiral centres. If the stereo- chemical conformations are opposite(i.e. 1R,2S or 1S,1R) the nameephedrine is used. If the conformationsare the same (1R,2R or 1S,2S)then the compound is called pseudoephedrine.

• 生物学の機能

  Ephedrine is a naturally occurring alkaloid that can cross the blood-brain barrier and thus exert a strong CNS-stimulating effect in addition to its peripheral actions.The latter effects are primarily due to its indirect actions and depend largely on the release of norepinephrine. However, ephedrine may cause some direct receptor stimulation, particularly in its bronchodilating effects. Because it resists metabolism by both COMT and MAO, its duration of action is longer than that of norepinephrine. As is the case with all indirectly acting adrenomimetic amines, ephedrine is much less potent than norepinephrine; in addition, tachyphylaxis develops to its peripheral actions. Unlike epinephrine or norepinephrine, however, ephedrine is effective when administered orally.

• 危険性

  Toxic by ingestion.

• 作用機序

  Ephedrine is a naturally occurring sympathomimetic amine that possesses both direct (agonist at α- and β-receptors) and indirect activity via its potentiation of noradrenaline release from sympathetic nerve terminals. It causes an increase in HR, contractility, CO and arterial pressure (systolic > diastolic). Bronchodilation occurs via a β2-mediated mechanism, and it is occasionally used for this purpose. Its duration of action is longer than endogenous catecholamines as it is not metabolised by COMT or MAO. Tachyphylaxis can occur as a result of depletion of noradrenaline from nerve terminals and persistent occupation of adrenergic receptors. Ephedrine crosses the placenta and can increase fetal metabolic rate with a subsequent metabolic acidosis. It is usually administered by i.v. bolus at a dose of 3– 9 mg.

• 薬理学

  Ephedrine increases systolic and diastolic blood pressure; heart rate is generally not increased. Contractile force of the heart and cardiac output are both increased. Ephedrine produces bronchial smooth muscle relaxation of prolonged duration when administered orally. Aside from pupillary dilation, ephedrine has little effect on the eye.

• 臨床応用

  Ephedrine is useful in relieving bronchoconstriction and mucosal congestion associated with bronchial asthma, asthmatic bronchitis, chronic bronchitis, and bronchial spasms. It is often used prophylactically to prevent asthmatic attacks and is used as a nasal decongestant, as a mydriatic, and in certain allergic disorders. Although its bronchodilator action is weaker than that of isoproterenol, its oral effectiveness and prolonged duration of action make it valuable in the treatment of these conditions. Because of their oral effectiveness and greater bronchiolar selectivity, terbutaline and albuterol are replacing ephedrine for bronchodilation.

• 副作用

  Symptoms of overdose are related primarily to cardiac and CNS effects. Tachycardia, premature systoles, insomnia, nervousness, nausea, vomiting, and emotional disturbances may develop. Ephedrine should not be used in patients with cardiac disease, hypertension, or hyperthyroidism.

• 安全性プロファイル

  A human poison by an unspecified route. An experimental poison by intravenous, subcutaneous, intramuscular, and intraperitoneal routes. Moderately toxic by ingestion and parented routes. Causes rapid pulse, rise in blood pressure, and other actions similar to epinephrine. An experimental teratogen. Used in production of drugs of abuse. Has been known to cause allergic sensitization. When heated to decomposition it emits toxic fumes of NOx.

• 純化方法

  Purify (-)-ephedrine by vacuum distillation (dehydrates) and forms waxy crystals or granules, and may pick up 0.5 H2O. The presence of H2O raises its melting point to 40o. [Moore & Taber J Amer Pharm Soc 24 211 1935.] The anhydrous base crystallises from dry ether [Fleming & Saunders J Chem Soc 4150 1955]. It gradually decomposes on exposure to light and is best stored in an inert atmosphere in the dark (preferably at -20o). Its solubility in H2O is 5%, in EtOH it is 1% and it is soluble in CHCl3, Et2O and mineral oils. It has pKa values in H2O of 10.25 (0o) and 8.69 (60o) [Everett & Hyne J Chem Soc 1136 1958, Prelog & H.flinger Helv Chim Acta 33 2021 1950] and pK a 8.84 in 80% aqueous methoxyethanol [Simon Helv Chim Acta 41 1835 1958]. The hydrochloride has m 220o (from EtOH/Et2O) and [] D20 -38.8o (c 2, EtOH). [IR: Chatten & Levi Anal Chem 31 1581 1959.] The anhydrous base crystallises from Et2O [Fleming & Saunders J Chem Soc 4150 1955]. [Beilstein 13 H 373, 13, III 1720, 13 IV 1879.]

エフェドリン 上流と下流の製品情報

エフェドリン スペクトルデータ(¹HNMR、FT-IR、IR、Raman)

299-42-3, エフェドリン キーワード