モルヒネ

モルヒネ 化学構造式
57-27-2
CAS番号.
57-27-2
化学名:
モルヒネ
别名:
4,5α-エポキシ-17-メチル-7,8-ジデヒドロモルフィナン-3,6α-ジオール;モルヒネ;(9α,13α,14α)-7,8-ジデヒドロ-4,5β-エポキシ-17-メチルモルフィナン-3,6β-ジオール;(5S,9α,13α,14α)-7,8-ジデヒドロ-4,5β-エポキシ-17-メチルモルフィナン-3,6β-ジオール;(+)-モルフィン;モルフィウム;7,8-ジデヒドロ-4,5α-エポキシ-17-メチルモルフィナン-3,6α-ジオール;(-)-モルフィン;モルフィナ;17-メチル-7,8-ジデヒドロ-4,5α-エポキシモルフィナン-3,6α-ジオール;(-)-モルヒネ;モルフィン;(5R,6S)-7,8-ジデヒドロ-4,5-エポキシ-17-メチルモルフィナン-3,6-ジオール;N-メチルナロルフィン;モルフィア;(1R,5S,13S,14R,17S)-4-メチル-12-オキサ-4-アザペンタシクロ[9.6.1.01,13.05,17.07,18]オクタデカ-7,9,11(18),15-テトラエン-10,14-ジオール
英語名:
MORPHINE
英語别名:
rms;MORPHINA;morph;Morphin;7,8-didehydro-4,5-alpha-epoxy-17-methyl-morphinan-6-alpha-diol;morpho;MORPHINE BASE;Morphine (CRM);PSEUDOMORPHINE;Dehydromorphine
CBNumber:
CB0680482
化学式:
C17H19NO3
分子量:
285.34
MOL File:
57-27-2.mol

モルヒネ 物理性質

融点 :
255°C
沸点 :
427.77°C (rough estimate)
比重(密度) :
1.0864 (rough estimate)
屈折率 :
1.5400 (estimate)
闪点 :
11 °C
貯蔵温度 :
−20°C
溶解性:
Ethanol (Slightly), Methanol (Slightly)
外見 :
Solid
酸解離定数(Pka):
8.21(at 25℃)
色:
White to Pale Yellow
水溶解度 :
0.4mg/L(25℃)
BCS Class:
1,3
CAS データベース:
57-27-2
EPAの化学物質情報:
Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl- (5.alpha.,6.alpha.)- (57-27-2)
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  F,T
Rフレーズ  11-23/24/25-39/23/24/25
Sフレーズ  7-16-36/37-45
RIDADR  UN 1230 3/PG 2
WGK Germany  2
有毒物質データの 57-27-2(Hazardous Substances Data)
毒性 An alkaloid of the opium poppy that makes up between 9% and 14% of good grades of opium. Morphine is usually used clinically as an analgesic in the form of the sulfate or hydrochloride salt. The most important acute toxic effect of large doses of morphine is depression of the respiratory centers in the medulla and pons. Morphine and related drugs also cause somnolence, coma, cold clammy skin, bradycardia, and hypotension. Initial doses of morphine seem to stimulate the chemoreceptor trigger zone to induce emesis, with subsequent doses blocking the vomiting center, hence blocking emesis. Morphine also has profound effects on the gastrointestinal tract, increasing the tone of the intestinal tract, but decreasing the propulsive or spasmodic reflexes, thus resulting in constipation. Morphine stimulates the nucleus of the third cranial nerve to produce miosis, making pinpoint pupil a diagnostic sign both in morphine overdose and morphine addiction. Morphine causes a variety of effects on the CNS and is highly addictive. Many behavioral changes are seen, ranging from euphoria to sedation. These behavioral effects contribute to the problem of abuse with all of the opiates. Tolerance and dependence occur with repeated dosing, with increasingly larger doses being needed to obtain the original effect. Abrupt withdrawal after chronic use can lead to physiological rebound in these same systems. Therapy for acute overdosage involves physiological support (establishment of adequate respiratory exchange), gastric lavage, and use of narcotic antagonists. Morphine and related compounds act by binding to specific high-affinity receptors concentrated in the nervous system, but also located elsewhere in the body. In the nervous system, the endogenous ligands for these morphine receptors are the opioid peptides that include the enkephalins, endorphins, and dynorphins. The multiple and complex actions of morphine are due, in part, to the fact that it acts as an agonist at many of these classes of receptors. Paregoric (camphorated tincture of opium) is used as an antidiarrheal. Paregoric is a schedule III drug under the US Controlled Substances Act and may produce physical dependence.
絵表示(GHS) GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
注意喚起語 危険
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
H225 引火性の高い液体および蒸気 引火性液体 2 危険 GHS hazard pictograms P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 GHS hazard pictograms P260, P264, P270, P307+P311, P321,P405, P501
注意書き
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P370+P378 火災の場合:消火に...を使用すること。
P403+P235 換気の良い場所で保管すること。涼しいところに 置くこと。

モルヒネ 価格

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

モルヒネ 化学特性,用途語,生産方法

解説

モルヒネ,白色針状または柱状晶.110 ℃ で水和水を失い,230 ℃ で分解し,紫色となる.d420"1.32.pKa 6.13.アルカリ水に易溶,熱メタノールに可溶,水に難溶.[α]D20"-132°(メタノール).λmax 285 nm(水).酸化を受けやすく,また光によって褐色となる.塩酸塩(塩酸モルヒネ)は,皮下注射後数分で作用が現れ,半時間で極点に達し,数時間後に衰え,約半日後に消失する.このような鎮痛作用と同時に,不快感を忘れさせ,恍惚(こうこつ)感を起こさせるので,習慣性,耽溺(たんでき)性があり,麻薬に指定されている.
森北出版「化学辞典(第2版)

用途

医療においては癌性疼痛をはじめ、各種の疾病および外傷による疼痛を緩和する目的で使用される。薬剤の剤形としては錠剤、散剤、液剤、坐剤、注射剤があり、それぞれ実情に応じて使用される。「モルフィン」「モヒ」とも言う。

製法

モルヒネ,ケシ科Papaver somniferumの未熟果中に含まれる.アヘンの主アルカロイドで,約10% 以上含有される.強力な麻酔鎮痛作用を有し,その名称はギリシア神話の眠りの神Morpheusに由来する.通常,一水和物で得られる.

効能

麻薬性鎮痛薬, オピオイド受容体作動薬

毒性

LD50 500 mg/kg(マウス,皮下).

説明

Morphine is the principal alkaloid obtained from opium. Opium is the resinous latex that exudes from the seed pod of the opium poppy, Papver somneferum, when it is lacerated. Alkaloids account for approximately 25% of opium, and of this 25% about 60% is morphine.

化学的特性

White, crystalline alkaloid. Slightly soluble in water,alcohol, and ether.

物理的性質

Appearance: white or almost white crystalline powder or colorless, silky needles or cubical masses, efflorescent in a dry atmosphere. Solubility: soluble in water, slightly soluble in ethanol, practically insoluble in chloroform or ether. Specific optical rotation: ?110.0° to 115.0°

来歴

Morphine has a strong analgesic effect, especially for moderate and severe cancer pain. However, morphine has serious side effects, such as addiction, respiratory depression, acute poisoning, and death. Therefore, in regulating the clinical application of morphine at the same time, it is necessary to explore the alternative to morphine with strong analgesic role and minor side effects.
In the 1970s, tramadol was launched and marketed as “Tramal” by the German pharmaceutical company Grünenthal GmbH in West Germany , and 20 years later, it was launched in countries such as the United Kingdom, the United States, and Australia. It is marketed in many brand names worldwide. After R&D of more than 100 years, opioid drugs were increased and have been widely used in clinic as analgesic drugs.

使用

A degradation product of Morphine. A dimolecular base formed by the gentle oxidation of Morphine in alkaline solution. Name Pseudomorphine is also used for the C17 alkaloid base

定義

ChEBI: A morphinane alkaloid that is a highly potent opiate analgesic psychoactive drug. Morphine acts directly on the central nervous system (CNS) to relieve pain but has a high potential for addiction, with tolerance and both physical and psychological dependen e developing rapidly. Morphine is the most abundant opiate found in Papaver somniferum (the opium poppy).

調製方法

Morphine is detoxified or biotransformed mainly in the liver by conjugation with glucuronic acid. Morphine is conjugated by a series of reactions involving the formation of uridine diphosphoglucose (UDP-glucose), the oxidation of carbon-6 of glucose to form uridine diphosphoglucuronic acid (UDP-glucuronic acid) and the transfer of glucuronic acid to morphine to form the morphine glucuronide. The following enzymes catalyze the sequential reactions; reaction(1), UDP-glucose pyrophosphorylase; reaction (2), UDP-glucose dehydrogenase; reaction (3), glucuronyl transferase; reaction (4) nucleoside diphosphokinase.

適応症

Morphine is mainly used to treat both acute and chronic severe pain. It is also used for pain caused by myocardial infarction and for labor pains. Morphine relieves pulmonary edema symptoms; anesthesia and preoperative administration can make the patient quiet and drowsy; compound formula of morphine was used for acute and chronic diarrhea.

獲得抵抗性

It is important to remember that a minor change in the structure of morphine (or any other opioid) will likely cause a different change in the affinity and intrinsic activity of the new compound at each of the opioid receptor types. Thus, the opioid receptor selectivity profile of the new compound may be different than the structure from which it was made or modeled (i.e., a selective μ agonist may shift to become a selective κ agonist, etc.). In addition, the new compound will have different physicochemical properties than its parent. The different physicochemical properties (e.g., solubility, partition coefficient, and pKa) will result in different pharmacokinetic characteristics for the new drug and can affect its in vivo activity profile. For example, a new drug (Drug A) that is more lipophilic than its parent may distribute better to the brain and appear to be more active, whereas in actuality, it may have lower affinity or intrinsic activity for the receptor. The greater concentration of Drug A reaching the brain is able to overcome its decreased agonist effect at the receptor.

危険性

Narcotic, habit-forming drug, salerestricted by law in the U.S.

接触アレルゲン

Morphine bitartrate caused contact dermatitis in a worker at a plant producing opium alkaloids. Morphine hydrochloride and morphine bitartrate showed patchtest- positive reactions in another patient with contact dermatitis working in the production of concentrated poppy straw. We observed a concomitant reaction between a morphine base and a codeine base in a patient with drug skin eruption due to codeine.

薬物動態学

Morphine is the prototype opioid. It is selective for μ opioid receptors. The structure of morphine is composed of five fused rings, and the molecule has five chiral centers with absolute stereochemistry 5(R), 6(S), 9(R), 13(S) and 14(R). The naturally occurring isomer of morphine is levo-[(–)] rotatory. (+)-Morphine has been synthesized, and it is devoid of analgesic and other opioid activities.

安全性プロファイル

Poison experimentally by ingestion, intracerebral, intraperitoneal, subcutaneous, and intravenous routes. Human reproductive effects by an unspecified route: effects on newborn, including drug dependence. Experimental reproductive effects. Mutation data reported.
Morphine is the constituent of opium most responsible for its toxic effects. When taken orally, the effects of morphine poisoning begin to appear in 20-40 minutes; if taken hypodermically, the symptoms appear much earlier and narcotism is more likely to follow the early symptoms. Abuse leads to habituation or adlction. Inlvidual susceptibility varies greatly and children are more susceptible than adults. When heated to decomposition it emits toxic fumes of NOx.

純化方法

Crystallise the narcotic from MeOH or anisole. It dehydrates at 130o. Its solubility in H2O is 0.2g/L at 20o and 0.9g/L at 100o, and in EtOH it is 5g/L at 20o and 10g/L on boiling. The styphnate has m 189o (from aqueous EtOH). [Beilstein 27 II 118, 27 III/IV 2223.]

参考文献

Derosne., Ann. Chirn., 45, 257 (1803)
Laurent., Ann. Chirn. Phys., 19, iii, 359 (1847)
Muller., Apoth. Zeit., 18, 257 (1903)
Mannich., Chern. Zentr., II, 820 (1916)
Emde., Helv. Chirn. Acta, 13, 1035 (1930)
Gates, Tschudi., 1. Arner. Chern. Soc., 78, 1380 (1956)
Crystal structure: MacKay, Hodgkin., 1. Chern. Soc., 3261 (1955)
Synthesis: Gates, TschudL,J. Arner. Chern. Soc., 74, 1109 (1952)
Elad, Ginsburg., ibid, 76,312 (1954)
Elad, Ginsburg., J. Chern. Soc., 3052 (1954)
Morrison, Waite, Shavel., Tetrahedron Lett., 4055 (1967)
NMR and mass spectra: Rull., Bull. Soc. Chim. Fr., 586 (1963)
Okuda et al., Chern. Pharrn. Bull. (Tokyo), 11, 1465 (1963)
Wheeler, Kinstle, Rinehart., J. Arner. Chern. Soc., 89,4494 (1967)
Biosynthesis: Barton et aI., J. Chern. Soc., 2423 (1965)
Pharmacology: Vahlen., Arch. expo Path. Pharrn., 47, 368 (1902)
Small et al., Public Health Reports, Suppl. 138, Washington (1938)
Krueger, Eddy, Sumwalt., ibid, No. 165, Washington (1943)

モルヒネ 上流と下流の製品情報

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モルヒネ 生産企業

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57-27-2(モルヒネ)キーワード:


  • 57-27-2
  • MORPHINE
  • EXTRACT OF OPIUM
  • CODEINE IMP B
  • Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl- (5a,6a)- (9CI)
  • Morphine (base and/or unspecified salts)
  • (5a,6a)-(5'a,6'a-7,7',8,8'-Tetradehydro-4,5:4',5'-diepoxy-17,17'-dimethyl-[2,2'-bimorphinan]-3,3',6,6'-tetrol
  • 2,2'-Dehydrodimorphine
  • Oxydimorphine
  • 7,8-didehydro-4,5alpha-epoxy-17-methyl-morphinan-6alpha-diol
  • 7,8-didehydro-4,5-epoxy-17-methyl-(5alpha,6alpha)-morphinan-6-diol
  • 7,8-didehydro-4,5-epoxy-17-methyl-morphinan-3,6-diol
  • 9H-9,9c-Iminoethanophenanthro(4,5-bcd)furan-3,5-diol, 4a,5,7a,8-tetrahydro-12-methyl-
  • 9h-9,9c-iminoethanophenanthro(4,5-bcd)furan-3,5-diol,4a,5,7a,8-tetrahydro-12
  • 9h-9,9c-iminoethanophenanthro(4,5-bcd)furan-3,5-diol,4a,5,7a,8-tetrahydro-12-m
  • cubejuice
  • D-(-)-Morphine
  • ms-contin
  • msemma
  • Nepenthe
  • Ospalivina
  • roxanol
  • 2,2-bimorphine
  • dreamer
  • Dulcontin
  • duramorph
  • Duromorph
  • hardstuff
  • hocus
  • l-Morphine
  • Meconium
  • 4,5α-エポキシ-17-メチル-7,8-ジデヒドロモルフィナン-3,6α-ジオール
  • モルヒネ
  • (9α,13α,14α)-7,8-ジデヒドロ-4,5β-エポキシ-17-メチルモルフィナン-3,6β-ジオール
  • (5S,9α,13α,14α)-7,8-ジデヒドロ-4,5β-エポキシ-17-メチルモルフィナン-3,6β-ジオール
  • (+)-モルフィン
  • モルフィウム
  • 7,8-ジデヒドロ-4,5α-エポキシ-17-メチルモルフィナン-3,6α-ジオール
  • (-)-モルフィン
  • モルフィナ
  • 17-メチル-7,8-ジデヒドロ-4,5α-エポキシモルフィナン-3,6α-ジオール
  • (-)-モルヒネ
  • モルフィン
  • (5R,6S)-7,8-ジデヒドロ-4,5-エポキシ-17-メチルモルフィナン-3,6-ジオール
  • N-メチルナロルフィン
  • モルフィア
  • (1R,5S,13S,14R,17S)-4-メチル-12-オキサ-4-アザペンタシクロ[9.6.1.01,13.05,17.07,18]オクタデカ-7,9,11(18),15-テトラエン-10,14-ジオール
  • 麻薬
  • 麻薬性鎮痛薬
  • 鎮咳薬
  • 制瀉薬
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