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マーキュロクロム

Mercury dibromofluorescein disodium salt

HCID 441373
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
129-16-8
標準SMILES
O.O=C([O-])c1ccccc1-c1c2cc(Br)c(=O)cc-2oc2[c]([Hg])c([O-])c(Br)cc12.[Na+].[Na+]
InChIKey
KQSRXDXJGUJRKE-UHFFFAOYSA-L
分子式
C20H9Br2HgNa2O6
平均分子量
751.7 g/mol
単同位体質量
750.82677

概要

Merbromin is an organic sodium salt that is 2,7-dibromo-4-hydroxymercurifluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions. It has a role as an antiseptic drug, a fluorochrome and a histological dye. It contains a 2,7-dibromo-4-hydroxymercurifluorescein(2-).

名称と識別子

優先名称
Mercury dibromofluorescein disodium salt
IUPAC
disodium;[2,7-dibromo-9-(2-carboxylatophenyl)-3-oxido-6-oxoxanthen-4-yl]mercury;hydrate
現地名
マーキュロクロム
英語名
MERBROMIN
分子式
C20H11Br2HgNaO6
分子量
730.69

名称と別名

Mercury dibromofluorescein disodium saltdisodium;[2,7-dibromo-9-(2-carboxylatophenyl)-3-oxido-6-oxoxanthen-4-yl]mercury;hydrateCinfacrominMerbrominoMercuriocromoSupercromeSodium merbrominSodium mercuresceinMerbromin N.F XIISCHEMBL25312SPECTRUM1500637orb1310778
名称をさらに表示
クロマルギルマキュロンキュリクロムシノクロムマーキュロブロカセプト[2',7'-ジブロモ-3',6'-ジ(ソジオオキシ)-3-オキソスピロ[イソベンゾフラン-1(3H),9'-[9H]キサンテン]-4'-イル]ヒドロキシ水銀(II)マーキュロクロムクロミンクロマギンアセプトクロムメルブロミンエルミールジブロモフルオレセイン水銀ジナトリウム塩水銀ジブロモフルオレセイン 二ナトリウム塩マーキュロクロム (JP17)マーキュロクロームエカクロム[2′,7′-ジブロモ-3′,6′-ジ(ソジオオキシ)-3-オキソスピロ[イソベンゾフラン-1(3H),9′-[9H]キサンテン]-4′-イル]ヒドロキシ水銀(II)エムセロールHg2sb2o7fluorochromeMERCUROCHROME

物性

構造計算による物性

極性表面積
90.5 Ų
水素結合供与体数
1
水素結合受容体数
6
回転可能結合数
2
重原子数
31
形式電荷
0
複雑度
801

物理化学的性質

融点
300 °C · ≥300 °C
貯蔵温度
Poison room
溶解性
50 mg/mL · Water : ≥ 50 mg/mL (66.43 mM);DMSO : 6.67 mg/mL (8.86 mM)
外見
結晶性
色
緑
臭い (Odor)
無臭
水溶解度
2.561 g/L · 2.561g/L at 25℃
Merck
13 · 13,5892
安定性
安定。強酸化剤、強酸とは相容れない。
InChI
InChI=1S/C20H9Br2O5.Hg.Na.H2O.H/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20;;;;/h1-7,23-24H;;;1H2;/q;+1;;;/p-1
InChIKey
DWCWFRMTTRCCLB-UHFFFAOYSA-M
SMILES
O=C1C2C=CC=CC=2C2(C3=CC(Br)=C(O)C=C3OC3C(=C(O)C(Br)=CC2=3)[Hg]O)O1.[NaH]
LogP
1.418 at · 1.418 at 25℃
CAS データベース
129 · 129-16-8(CAS DataBase Reference)
EPAの化学物質情報
Mercury, (2',7'-dibromo-3',6'-dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-4'-yl)hydroxy-, disodium salt (129-16-8)

化学的性質

化学的特性dark green solid

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

安全と保護具

Minimum Risk LevelChronic Inhalation: 0.0002 mg/m3 (Mercury) (L134)

毒性情報

Treatment · 1 件

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 件

Mercury mainly affects the nervous system. Exposure to high levels of metallic, inorganic, or organic mercury can permanently damage the brain, kidneys, and developing fetus. Effects on brain functioning may result in irritability, shyness, tremors, changes in vision or hearing, and memory problems. Acrodynia, a type of mercury poisoning in children, is characterized by pain and pink discoloration of the hands and feet. Mercury poisoning can also cause Hunter-Russell syndrome and Minamata disease. Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627, L7)

Exposure RoutesOral (L7) ; inhalation (L7) ; dermal (L7)
Toxicity Summary · 1 件

High-affinity binding of the divalent mercuric ion to thiol or sulfhydryl groups of proteins is believed to be the major mechanism for the activity of mercury. Through alterations in intracellular thiol status, mercury can promote oxidative stress, lipid peroxidation, mitochondrial dysfunction, and changes in heme metabolism. Mercury is known to bind to microsomal and mitochondrial enzymes, resulting in cell injury and death. For example, mercury is known to inhibit aquaporins, halting water flow across the cell membrane. It also inhibits the protein LCK, which causes decreased T-cell signalling and immune system depression. Mercury is also believed to inhibit neuronal excitability by acting on the postsynaptic neuronal membrane. It also affects the nervous system by inhibiting protein kinase C and alkaline phosphatase, which impairs brain microvascular formation and function, as well as alters the blood-brain barrier. Organic mercury exerts developmental effects by binding to tubulin, preventing microtubule assembly and causing mitotic inhibition. Mercury also produces an autoimmune response, likely by modification of major histocompatibility complex (MHC) class II molecules, self peptides, T-cell receptors, or cell-surface adhesion molecules. Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543, L7, A8, A25, A26)

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Organic mercury is absorbed mainly by the gastrointestinal tract, then distributed throughout the body via the bloodstream. Organic mercury complexes with free cysteine and the cysteine and sulfhydryl groups on proteins such as haemoglobin. These complexes are able to mimic methionine and thus be transported throughout the body, including through the blood-brain barrier and placenta. Organic mercury is metabolized into inorganic mercury, which is eventually excreted in the urine and faeces. Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626, T11)

用途と製造

UsesMerbromin is used as a topical antiseptic for minor cuts and scrapes. It is also used as a biological dye to mark tissue margins, and as a metal dye in industrial dye penetrant inspection to detect metal fractures. (L264)
応用分野 · 3 件

解説化学式はC2(/0)H8O6Br2Na2Hg。防腐殺菌剤。ジブロムフルオレセインの水銀化合物のナトリウム塩。メルブロミンとも。黄緑〜帯緑赤褐色の鱗片状結晶,無臭。創傷の消毒に2%水溶液(赤チン)を用いる。刺激がないので賞用されるが赤色の強いのが欠点。副作用として局所に発疹やかゆみを生ずることがある。水銀化合物の公害問題で国内での製造は停止されているが,輸入品の使用は禁止されていない。→関連項目消毒薬株式会社平凡社 百科事典マイペディアについて 情報

用途マーキュロクロムは,殺菌消毒剤、有機水銀化合物。青緑色ないし帯緑赤褐色の小葉状または粒状で、においはなく、水によく溶け、水溶液は赤色を呈し、黄緑色の蛍光を発する。通常,これの1~2%水溶液(マーキュロクロム液)として使用される。マーキュロクロム液は,色が赤いため俗に〈赤チン〉ともいわれ,細菌発育抑制作用があって,局所刺激性が少ないため,創傷,皮膚粘膜の消毒に用いられる。しかし,マーキュロクロムを含め,有機水銀製剤は基本的には作用は静菌的であり,浸透性も弱いので,芽胞を殺すのには使用できない。刺激性のない緩和な消毒剤として皮膚、粘膜に塗布する。水銀イオンが解離して殺菌作用を現すが、殺菌作用はあまり強くない。皮膚・粘膜の消毒のほか、創面の消毒はもとより、洗浄、点眼・洗眼にも用いられたことがある。刺激性のないこと、金属を腐食しないことが利点であるが、着色が強いのが欠点である。水銀化合物であるので、製造時における公害が問題となり、日本では製造されていない。使用量も激減している。ヨードチンキとの併用は水銀が析出するので避けなければならない。[幸保文治]

使用anthelmintic

調製方法 · 1 件

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0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
domf
Emcerol
flavurol
Chromine
Ekakrome
MERBROMIN
Marbromin
HMS501E17DTXSID701015061HMS1921M15HMS2092E12CCG-39726AKOS015903744AKOS037515483DB13392

データベース識別子

CAS
129-16-8、15015-80-2
PubChem CID
441373
DTXSID
DTXSID701015061
ChEBI
CHEBI:6763
Signs and Symptoms · 1 件

Common symptoms include peripheral neuropathy (presenting as paresthesia or itching, burning or pain), skin discoloration (pink cheeks, fingertips and toes), edema (swelling), and desquamation (dead skin peels off in layers). Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627, A5)

Carcinogen ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)
Toxicity DataLD50: 50 mg/kg (Intravenous, Mouse) (L330)

安全データ

wgk
3
rtecs
LM5250000
ridadr
UN 2025 6.1/PG 2
毒性
mouse,LD50,intravenous,50mg/kg (50mg/kg),Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 645, 1931.
risk_code
26/27/28-33-50/53
hazard_code
T+,N
safety_code
13-28-36-45-60-61
hazard_class
6.1(a)
packing_group
II
Hazard Classifications
Acute Tox. 1 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2
ストレージクラス
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
有毒物質データの
129-16-8(Hazardous Substances Data)

純化方法The Na salt is dissolved in the minimum volume of H2O, or the free acid suspended in H2O and dilute NaOH is added to cause it to dissolve, filter and acidify it with dilute HCl. Collect the precipitate, wash it with H2O by centrifugation and dry it in a vacuum. The di Na salt can be purified by dissolving it in the minimum volume of H2O and is precipitated by adding EtOH, filter, wash it with EtOH or Me2CO and dry it in a vacuum. Its solubility in 95% EtOH is 2% and in MeOH it is 16%. [White J Am Chem Soc 42 2355 1920.]

上流・下流製品情報

上流原料

レソルシノールフタル酸水銀(II)オキシド

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補足説明

定義ChEBI: An organic sodium salt that is 2,7-dibromo-4-hydroxymercurifluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.