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Substance Name: Methylene blue
RN: 61-73-4
UNII: 8NAP7826UB
InChIKey: CXKWCBBOMKCUKX-UHFFFAOYSA-M

Note

  • A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.

Molecular Formula

  • C16-H18-N3-S.Cl

Molecular Weight

  • 319.8582
 

Classification Codes

  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Results Name

  • Methylene blue

Name of Substance

  • 3,7-Bis(dimethylamino)phenothiazin-5-ium chloride
  • Basic Blue 9
  • CI 52015
  • Methylene blue
  • Methylene Blue anhydrous
  • Methylthioninium chloride [INN]
  • Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride

MeSH Heading

  • Methylene blue

Synonyms

  • 3,7-Bis(dimethylamino)phenazathionium chloride
  • 3,7-Bis(dimethylamino)phenothiazin-5-ium chloride
  • Aizen Methylene Blue BH
  • Aizen Methylene Blue FZ
  • Basic Blue 9
  • Bleu de methylene
  • C.I. 52015
  • C.I. Basic Blue 9
  • Calcozine Blue ZF
  • Caswell No. 567
  • CCRIS 833
  • Ceruleum methylenum
  • Chlorure de methylthioninium
  • Chlorure de methylthioninium [INN-French]
  • Chromosmon
  • CI 52015
  • CI Basic Blue 9
  • Cloruro de metiltioninio
  • Cloruro de metiltioninio [INN-Spanish]
  • D and C Blue No. 1
  • D And C Blue Number 1
  • EINECS 200-515-2
  • EPA Pesticide Chemical Code 039505
  • Ext D and C Blue No. 1
  • External Blue 1
  • Hidaco Methylene Blue Salt Free
  • HSDB 1405
  • Leather Pure Blue HB
  • M-B Tabs
  • Methylenblau
  • Methylenblau [German]
  • Methylene blue
  • Methylene Blue (medicinal)
  • Methylene Blue 2B
  • Methylene Blue 2BF
  • Methylene Blue 2BN
  • Methylene Blue 2BP
  • Methylene Blue A
  • Methylene Blue B
  • Methylene Blue BB
  • Methylene Blue BB (zinc free)
  • Methylene Blue BBA
  • Methylene Blue BD
  • Methylene Blue BP
  • Methylene Blue BPC
  • Methylene Blue BX
  • Methylene Blue BZ
  • Methylene Blue chloride
  • Methylene Blue chloride (biological stain)
  • Methylene Blue D
  • Methylene Blue FZ
  • Methylene Blue G
  • Methylene Blue GZ
  • Methylene Blue HGG
  • Methylene Blue I (medicinal)
  • Methylene Blue IAD
  • Methylene Blue JFA
  • Methylene Blue N
  • Methylene Blue NF (medicinal)
  • Methylene Blue NZ
  • Methylene Blue Polychrome
  • Methylene Blue SG
  • Methylene Blue SP
  • Methylene Blue USP (medicinal)
  • Methylene Blue USP XII (medicinal)
  • Methylene Blue ZF
  • Methylene Blue Zinc Free
  • Methylene Blue ZX
  • Methylenium ceruleum
  • Methylenum coeruleum
  • Methylthionine chloride
  • Methylthionini chloridum
  • Methylthioninii chloridum
  • Methylthioninii chloridum [INN-Latin]
  • Methylthioninium chloride
  • Methylthionium chloride
  • Metiltioninio cloruro
  • Metiltioninio cloruro [DCIT]
  • Mitsui Methylene Blue
  • Modr Methylenova
  • Modr Methylenova [Czech]
  • Modr Rozpoustedlova 8
  • Modr Rozpoustedlova 8 [Czech]
  • Modr Zasadita 9
  • Modr Zasadita 9 [Czech]
  • NSC 215213
  • Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride
  • Provayblue
  • Rember
  • Sandocryl Blue BRL
  • Schultz No. 1038
  • Solvent Blue 8
  • Swiss Blue
  • Tetramethylene Blue
  • Tetramethylthionine chloride
  • UNII-8NAP7826UB
  • Urolene Blue
  • X 138
  • Yamamoto Methylene Blue B
  • Yamamoto Methylene Blue ZF

Systematic Names

  • 3H-Phenothiazine, 7-(dimethylamino)-3-(methylimino)-, 3-methochloride
  • C.I. Basic Blue 9 (8CI)
  • Methylene blue
  • Methylthioninium chloride
  • Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride
  • Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride (1:1)

Superlist Names

  • C.I. Basic Blue 9
  • Methylene blue

Registry Numbers

CAS Registry Number

  • 61-73-4

FDA UNII

  • 8NAP7826UB

Other Registry Numbers

  • 1001913-24-1
  • 1001914-35-7
  • 105504-42-5
  • 121067-62-7
  • 1219638-11-5
  • 12262-49-6
  • 1341-90-8
  • 167498-52-4
  • 6476-03-5
  • 923927-02-0
  • 97130-83-1

System Generated Number

  • 0000061734

Molecular Formulas

Molecular Formula

  • C16-H18-N3-S.Cl

Molecular Formula Fragments

  • C16-H18-N3-S
  • Cl
  • COMPONENT

Structure Descriptors

InChI

1S/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

InChIKey

CXKWCBBOMKCUKX-UHFFFAOYSA-M

Smiles

CN(C)c1ccc2c(c1)[s+]c3cc(ccc3n2)N(C)C.[Cl-]

Toxicity

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) BLOOD: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
"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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 105 dec deg C   EXP
log P (octanol-water) 5.850 (none)   EST
Water Solubility 4.36E+04 mg/L 25 EXP
Vapor Pressure 1.30E-07 mm Hg 25 EST
Henry's Law Constant 1.25E-12 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.05E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.