基本情報
- CAS
7220-79-3- 標準SMILES
CN(C)c1ccc2nc3ccc(=[N+](C)C)cc-3sc2c1.O.O.O.[Cl-]- InChIKey
XQAXGZLFSSPBMK-UHFFFAOYSA-M- 分子式
- C16H18N3S.Cl.3H2O
- 平均分子量
- 373.9 g/mol
- 単同位体質量
- 373.12269031
概要
Methylene blue trihydrate appears as odorless or almost odorless dark green crystals with bronze luster or dark green crystalline powder. pH (1% solution in water) 3 to 4.5. (NTP, 1992)
名称と識別子
- 優先名称
- Methylene Blue Trihydrate
- IUPAC
- [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium;chloride;trihydrate
- 現地名
- メチレンブルー
- 英語名
- Methylene Blue trihydrate
- 分子式
- C16H20ClN3OS
- 分子量
- 337.87
名称と別名
Methylene Blue trihydrate7220-79-3Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride, trihydrateDTXSID00256003,7-Bis(dimethylamino)phenothiazin-5-ium chloride trihydrateMethylene blue (USP)C.I. Basic Blue 9, trihydrateCCRIS 9312UNII-T42P99266KMethylene blue [USP]DTXCID705600METHYLENE BLUE TRIHYDRATE [MI]
名称をさらに表示
メチレンブルー三水和物3,7-ビス(ジメチルアミノ)フェノチアジン-5-イウム·クロリド·3水和物メチレンブルー二水和物メチレンブルー三水和物 (メチレンブルー)メチレンブルー二~三水和物メチレンブルー三水和物標準品メチレンブルー 溶液メチレンブルー 三水和物3,7-ビス(ジメチルアミノ)フェノチアジン-5-イウム・クロリド・3水和物メチレンブルー塩化メチルチオニニウムMETHYLENE BLUE HYDRATECI 52015Methylthioninium Chloride TrihydrateMethylthioniniumMethylene Blue, CPMETHYLTHIONINE CHLORIDEMETHYLENE BLUE CHLORIDEMETHYLENE BLUE INDICATORMethylene Blue trihydrateeMethyltltioninium Chloride
物性
構造計算による物性
- 極性表面積
- 46.9 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 7
- 回転可能結合数
- 1
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 483
実験および物理化学的性質
Chemical ClassesDyes -> Azine Dyes
Solubilitygreater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
Melting Point374 °F (decomposes) (NTP, 1992)
Physical Description
Methylene blue trihydrate appears as odorless or almost odorless dark green crystals with bronze luster or dark green crystalline powder. pH (1% solution in water) 3 to 4.5. (NTP, 1992)
Dark green odorless solid with a bronze luster; [Merck Index] Hygroscopic; [CAMEO] Dark green powder; [Sigma-Aldrich MSDS]
物理化学的性質
- 融点
- 190 °C · 190 °C (dec.)(lit.)
- 比重(密度)
- 0.98 g/mL · 0.98 g/mL at 25 °C
- 闪点
- 14 °C · 14 °C
- 貯蔵温度
- no restrictions.
- 溶解性
- 水、クロロホルムに可溶。エタノールにやや溶けにくい
- 外見
- 個体
- 酸解離定数(Pka)
- 2.6 · 2.6, 11.2(at 25℃)
- 色
- 緑
- PH
- 3 · 3 (20°C, 10g/L in H2O)
- 水溶解度
- 4 g/100mL · 4g/100mL
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。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 7.6% (7 of 92) of reports.
Warning
H302 (92.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 92 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationMethylene blue trihydrate: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound via ingestion include nausea, vomiting, diarrhea and dysuria. Ingestion of large amounts may cause hemolytic anemia. This compound causes skin irritation and severe eye irritation. Eye contact may result in corneal and conjunctival injury, stinging sensation, epiphora and, rarely, transient spasm of accommodation and blue coloration of the vitreous humor. Intravenous exposure to large amounts may cause nausea, abdominal pain, chest pain, headache, dizziness, mental confusion and profuse sweating. Subcutaneous exposure may lead to necrotic abscesses. Intrathecal injection may cause quadriplegia.
Hazards Summary
A skin and severe eye irritant; Toxic by ingestion (nausea, vomiting, diarrhea, dysuria, and hemolytic anemia from large doses); Repeated-dose oral studies of rats and mice demonstrated methemoglobinemia and a regenerative Heinz body anemia with secondary organ injury; Some evidence of carcinogenicity in male rats and mice, equivocal evidence in female mice, and no evidence in female rats; [NTP] A skin and strong eye irritant; Harmful by ingestion; Targets the blood, CNS, and eyes; May induce methemoglobinemia; [Sigma-Aldrich MSDS] See Methylene blue.
化学と産業
用途と製造
Uses
Used as a bacteriological stain, redox colorimetric agent, and in medicine (antimethemoglobinic); [Merck Index] Used to dye cotton and wool; [NTP]
Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
Household ProductsInformation on 2 consumer products that contain Methylene blue in the following categories is provided:
応用分野
用途チアジン染料、塩基性染料など。
用途滴定用指示薬、吸着試験用色素、顕微鏡用色素。
使用Methylene Blue trihydrate finds many uses in biology and chemistry. It acts as a GCS inhibitor, biological stain and redox indicator. It inhibits tau filament formation. Further, it is reported to bind to the M2 subtype of muscarinic receptors in rat cardiac myocytes and thus exhibit antimuscarinic effects on IK, ACh and ICa. It also inhibits endothelium-dependent relaxation of isolated blood vessels.
一般的な説明Methylene blue trihydrate appears as odorless or almost odorless dark green crystals with bronze luster or dark green crystalline powder. pH (1% solution in water) 3 to 4.5. (NTP, 1992)
調製方法
製造方法Methylene blue is synthesized commercially by oxidation of N,N-dimethyl-phenylenediamine with sodium dichromate (Na2Cr2O7) in the presence of sodium thiosulfate (Na2S2O3), followed by further oxidation in the presence of N,N-dimethylaniline (NTP, 2008). Methylene blue hydrochloride is isolated by addition of 30% hydrochloric acid and of a saturated common salt solution to the dye solution; after filtration, the product is washed with a 2% common salt solution. Instead of sodium dichromate, manganese dioxide, and catalytic amounts of copper sulfate can be used for the oxidation (Berneth, 2008). Methylene blue of high purity can be obtained by chloroform extraction of impurities from solutions of raw dye in borate buffer at pH 9.5–10, followed by acidification of the aqueous solution and isolation of the dye (Berneth, 2008).IARC Monographs
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