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61-73-4

Basic Information
CAS No.: 61-73-4
Name: Phenothiazin-5-ium,3,7-bis(dimethylamino)-, chloride (1:1)
Molecular Structure:
Molecular Structure of 61-73-4 (Phenothiazin-5-ium,3,7-bis(dimethylamino)-, chloride (1:1))
Formula: C16H18ClN3S
Molecular Weight: 319.88
Synonyms: C.I. BasicBlue 9 (6CI,8CI);Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride (9CI);Basic Blue 9;C.I. Solvent Blue 8;Calcozine Blue ZF;Izit Crystal Dye;Leather Pure Blue HB;Methylene Blue 2B;Methylene Blue 2BN;Methylene Blue2BP;Methylene Blue A;Methylene Blue BB;Methylene Blue BP;Methylene Blue BPC;Methylene Blue BX;Methylene Blue FZ;Methylene Blue G;MethyleneBlue SG;Methylene Blue SP;Methylene Blue ZF;Methylene Blue ZX;Methylene bluepolychrome;NSC 617593;Sandocryl Blue BRL;Schultz 1038;Solvent Blue 8;Tetramethylthioninechloride;Urolene Blue;Virostat;Yamamoto Methylene Blue B;Yamamoto MethyleneBlue ZF;
EINECS: 200-515-2
Density: 1.0 g/mL at 20 °C
Melting Point: 190 °C (dec.)(lit.)
Boiling Point: N/A
Flash Point: 45 °C
Solubility: 40 g/L (20 °C) in water
Appearance: green fine crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 10-41-22-20/21/22
Safety: 26-39-36
Transport Information: UN 1993 3/PG 3
PSA: 47.38000
LogP: -0.49710
Synthetic route

sodium hexacyanoferrate(II)

61-73-4

methylene blue

A

sodium hexacyanoferrate(III)

B

613-11-6

Leuco-Methylenblau

Conditions
ConditionsYield
With hydrogenchloride Kinetics; UV;
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  • Basic Blue 9/ 61-73-4

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Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Specification

The IUPAC name of Methylthioninium chloride is [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium chloride. With the CAS registry number 61-73-4, it is also named as 3,7-Bis(dimethylamino)phenothiazin-5-ium chloride; Methylene blue. The product's categories are analytical chemistry; ion association. It is green fine crystalline powder which is soluble in water and slightly soluble in ethanol. When burning it can produce toxic oxides fumes of nitrogen, chloride and sulfur, so the storage environment should be ventilate, low-temperature and dry.

The other characteristics of this product can be summarized as: (1)#H bond acceptors: 3; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 1; (4)Rotatable Bond Count: 1; (5)Exact Mass: 319.090996; (6)MonoIsotopic Mass: 319.090996; (7)Topological Polar Surface Area: 43.9; (8)Heavy Atom Count: 21; (9)Covalently-Bonded Unit Count: 2.

Preparation of Methylthioninium chloride: Using N, N-dimethyl aniline as the main raw material. Firstly, we get amino dimethyl aniline by nitrosation and reduction. Secondly, it is oxidized by Na2Cr2O7.Na2S2O3, and vulcanization and condensation to obtain thiazide. And finally, using ZnCl2 to salt, we can get the product by filtration and drying.

Uses of Methylthioninium chloride: It is not only used to dye cotton, acrylic, hemp, silk, but also used to color paper and wood. And it is also used in the manufacture of ink and color lakes. In addition, it is used in Biological stain and redox indicator.

When you are using this chemical, please be cautious about it as the following:
It is flammable and harmful by inhalation, in contact with skin and if swallowed. Especially, it is risk of serious damage to the eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing. 

People can use the following data to convert to the molecule structure.
1. SMILES: [Cl-].N=1c3c(SC=2C=1\C=C/C(=[N+](/C)C)/C=2)cc(cc3)N(C)C;
2. InChI: InChI=1/C16H18N3S.ClH/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/q+1;/p-1.

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 41mg/kg (41mg/kg)   Annals of Internal Medicine. Vol. 7, Pg. 738, 1933.
dog LDLo intravenous 50mg/kg (50mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
dog LDLo oral 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
domestic animals - goat/sheep LD50 intravenous 42300ug/kg (42.3mg/kg)   Journal of Veterinary Pharmacology and Therapeutics. Vol. 7, Pg. 225, 1984.
 
guinea pig LDLo subcutaneous 300mg/kg (300mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
infant TDLo unreported 15mg/kg (15mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BLOOD: OTHER CHANGES
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 390, 1969.
man TDLo subcutaneous 28uL/kg (0.028mL/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Journal of Clinical Practice. Vol. 28, Pg. 289, 1974.
 
monkey LDLo intravenous 10mg/kg (10mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 intravenous 77mg/kg (77mg/kg)   Cesko-Slovenska Farmacie. Vol. 12, Pg. 94, 1963.
 
mouse LD50 oral 3500mg/kg (3500mg/kg)   Cesko-Slovenska Farmacie. Vol. 12, Pg. 94, 1963.
 
rabbit LDLo oral 1gm/kg (1000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
rat LD50 intraperitoneal 180mg/kg (180mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 204, Pg. 288, 1947.
rat LD50 intravenous 1250mg/kg (1250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 676, 1968.
 
rat LD50 oral 1180mg/kg (1180mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1334, 1986.
rat LD50 subcutaneous 190mg/kg (190mg/kg)   Drugs in Japan Vol. -, Pg. 1185, 1990.