Name | Methylene Blue trihydrate |
Synonyms | Methylene Blue, CP Methylene Blue trihydrate Methylene Blue trihydratee Methyltltioninium Chloride Tetramethylthionine chlorideC.I. 52015 trihydrate Methylene Blue trihydrateBasic Blue 9 trihydrateC.I. 52015 trihydrate (7-Dimethylaminophenothiazin-3-ylidene)-dimethylazanium chloride trihydrate 3,7-bis(Dimethylamino)phenazathionium chloride, Basic Blue 9, Tetramethylthionine chloride |
CAS | 7220-79-3 |
EINECS | 615-731-6 |
InChI | InChI=1/C16H18N3S.ClH.3H2O/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13;;;;/h5-10H,1-4H3;1H;3*1H2/q+1;;;;/p-1 |
InChIKey | YAFGUSOAMIMROI-UHFFFAOYSA-M |
Molecular Formula | C16H24ClN3O3S |
Molar Mass | 373.9 |
Density | 0.98 g/mL at 25 °C |
Melting Point | 190°C (dec.)(lit.) |
Flash Point | 14°C |
Water Solubility | 4 g/100 mL |
Solubility | Soluble in water, chloroform; sparingly soluble in ethanol |
Appearance | Solid |
Color | Green |
Maximum wavelength(λmax) | ['668 nm, 609 nm'] |
Merck | 13,6085 |
pKa | 2.6, 11.2(at 25℃) |
Storage Condition | no restrictions. |
Stability | Stable. Incompatible with bases, reducing agents, strong oxidizing agents. |
Use | Used as redox indicator, adsorption indicator and biological stain |
Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R11 - Highly Flammable |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. |
UN IDs | UN 1170 3/PG 2 |
WGK Germany | 3 |
RTECS | SP5740000 |
TSCA | Yes |
HS Code | 32129000 |
color index | 52015 |
biological field application | Diagnosis of tauopathy,Alzheimer's disease (AD),Pick's disease; treating prophylaxis; Dental materials |
(IARC) carcinogen classification | 3 (Vol. 108) 2016 |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
action | methylene blue was first synthesized with zinc chloride salt in 1876, and then mainly used for:(1) methemoglobinemia: low concentration methylene blue is used to treat methemoglobinemia caused by nitrite, chlorate, quinones, quinones, imines, aniline and nitrobenzene;(2) cyanide poisoning: high concentration methylene blue can be used for cyanide poisoning;(3) combined with local anesthetics for local pain relief;(4) in recent years, clinical trials have also been used to treat infectious and traumatic shock, cancer, herpes zoster, etc. Pharmacological studies have shown that methylene blue has detoxification, analgesic, antibacterial, antiviral, anti-tumor, and can correct hemodynamic disorders in patients with septic shock and treat priapism. |
application | methylene blue is widely used in chemical indicators, dyes, biological stains and drugs. Especially in the dyeing industry, it is used to make inks, etc., with a large amount of use. In the following fields, methylene blue is also widely used. 1 Methylene blue in the industrial field belongs to dye compounds. Industrial grade methylene blue is often used for dyeing cotton, silk, paper, etc. It can also be used for coloring bamboo and manufacturing inks, lakes, etc. In addition, it is often used as a bacterial stain, indicator, etc. Methylene blue has been used in medicine for a long time. Due to the redox properties of methylene blue, it can be used to relieve cyanide, nitrite, aniline, acetanilide poisoning, or methemoglobin caused by sulfonamides and other drugs. In recent years, scholars have also studied the application of methylene blue and its metabolites in various bacterial and viral infections, cancer and central nervous system diseases such as depression, schizophrenia, Alzheimer's disease and other diseases. 3 In the field of aquaculture, methylene blue can be used as a disinfectant in the aquaculture of aquatic products. The principle is that the ionic compounds formed by methylene blue in the aqueous solution can compete with the microbial enzyme system for hydrogen ions and inactivate the enzyme. Lead to the loss of viability of microorganisms; it also has a certain effect in the treatment of fish diseases such as small melon disease, oblique tube disease, red mouth disease, water mold and larval mucus disease of Litopenaeus vannamei, and can also be used as anti-fungal drugs, reduce mortality in fish transportation. Studies in the field of skin care have shown that methylene blue also has certain potential in skin care. Methylene blue can scavenge free radicals and stimulate cell proliferation in young and old dermal fibroblasts, thus improving skin vitality, promoting skin elasticity and collagen synthesis, and protecting skin matrix through the degradation of matrix metalloproteinases. Therefore, methylene blue can become a promising agent in anti-aging cosmetics. |
harm | methylene blue can cause symptoms such as Heinz-body anemia, changes in red blood cell morphology, and necrotic swelling. Methylene blue is mutagenic. After intravenous injection of methylene blue with a dose of more than 500 mg/kg into the human body, it will make people feel nausea, dizziness, chest pain, etc. By comparing the acute toxicity experiments on different fish and shrimp and other aquatic animals, it is found that the toxicity of methylene blue to different aquatic animals is different, and when it reaches a certain concentration, a slight increase will cause a large number of animal deaths. Therefore, methylene blue needs to be used within its safe concentration. |
preparation | weigh 2mol(418g) of p-aminomethylaniline hydrochloride, put it into a reaction kettle with a thermometer, add 6L of water to dissolve, add 0.41mol(40g) of concentrated sulfuric acid dropwise under stirring to make the solution acidic, add zinc chloride solution, aluminum sulfate solution, sodium thiosulfate solution and 300mL of sodium dichromate solution in sequence at room temperature, under stirring, the reaction solution is heated to 40 ℃ within 10 minutes, the hydrochloric acid solution of N,N-dimethylaniline is put into the reaction kettle, then the remaining 600mL sodium dichromate solution is immediately added, and the reaction solution is heated to 70 ℃ within 10 minutes; When the temperature reaches 70 ℃, 2.87mol(250g) of manganese dioxide is put into the reaction kettle, heated to 85 ℃, maintained at the temperature for 30 minutes, and naturally cooled to 50 ℃, 7.14mol(700g) of concentrated sulfuric acid is slowly added under stirring; After stirring well, the reaction solution is released, and the reaction solution is placed at 4 ℃ for 5 hours, precipitation is precipitated, filtration is carried out, and the filter cake is washed with 600mL of 10% sodium chloride aqueous solution. Transfer the filter cake to a 20L beaker, add 10L of water, stir and heat on an electric heating sleeve until boiling, filter while hot, add 1.84mol(250g) of zinc chloride and 25.64mol(1500g) of sodium chloride into the filtrate, stir to dissolve, then place the solution at 4 ℃ for 24 hours, filter by suction, and dry at 50 ℃ to obtain 460g of methylene blue zinc chloride salt. Dissolve the obtained zinc chloride salt in 10L of water, add 0.52mol(55.2g) of sodium carbonate, cool to room temperature, filter by suction, wash the filter cake with a small amount of water, add 17.09mol(1000g) of sodium chloride, stir and dissolve, place at 4 ℃ for 12 hours, filter by suction, the filter cake was dried at 40-45 ℃ for 12 hours to obtain 320g of crude methylene blue (loss on drying was about 15%, and the yield was 42.5% based on anhydrous). The crude methylene blue product is put into a triangular flask, 1280mL(1: 4) of 0.1mol/L hydrochloric acid is added, dissolved in water bath at 60 ℃, crystallized at room temperature, filtered by suction, the filter cake is recrystallized once in hydrochloric acid of the same volume and concentration, recrystallized once in water of the same volume, the filter cake is dried at 40-45 ℃ for 12 hours to obtain 205g of methylene blue, the weight loss on drying is 14.6%, and the yield is 64.3% calculated by anhydrous. According to the raw material p-amino dimethylaniline hydrochloride, the total yield is 27.4%. |
use | mainly used for dyeing cotton, acrylic fiber, hemp, silk and paper, also used for coloring bamboo and wood, used to make ink and lake, and also used for dyeing biological bacteria used as redox indicator, adsorption indicator and biological stain bacterial stain. Serum protein biochemical test with mixed indicator. Prepare exfoliated cell test staining solution. Preparation of alkaline methylene blue staining solution. Redox indicator. Determination of mercury and tin. Reduced titrant to precipitate perchlorate and rhenate. Photometric determination of selenium and molybdenum in collaboration with others. |