Methylene blue

Methylene blue
INN: Methylthioninium chloride
	Molecular structure
	A volumetric flask of a methylene blue solution
Clinical data
Trade names	Urelene blue, Provayblue, Proveblue, others
Other names	CI 52015, basic blue 9
AHFS/Drugs.com	Monograph
License data	US DailyMed: Provayblue;
Pregnancy; category	AU: D;
Routes of; administration	By mouth, intravenous
ATC code	V03AB17 (WHO) V04CG05 (WHO);
Legal status
Legal status	US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Elimination half-life	5–24 hours (IVTooltip intravenous therapy)
Excretion	Renal; In rats: 18%(POTooltip Oral administration), 28% (IV)
Identifiers
	IUPAC name 3,7-bis(Dimethylamino)-phenothiazin-5-ium chloride;
CAS Number	61–73–4 ;
PubChem CID	6099;
DrugBank	DB09241 ;
ChemSpider	5874 ;
UNII	8NAP7826UB;
KEGG	D10537; C00220;
ChEBI	CHEBI:6872 ;
ChEMBL	ChEMBL405110 ;
CompTox Dashboard (EPA)	DTXSID0023296 ;
ECHA InfoCard	100.000.469
Chemical and physical data
Formula	C16H18ClN3S
Molar mass	319.85 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)c1ccc2c(c1)sc-3cc(=[N+](C)C)ccc3n2.[Cl-];
	InChI 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 ; Key:CXKWCBBOMKCUKX-UHFFFAOYSA-M ;
	(verify)

Methylthioninium chloride, commonly called methylene blue, is a salt used as a dye and as a medication. As a medication, it is mainly used to treat methemoglobinemia. It has previously been used for treating cyanide poisoning and urinary tract infections, but this use is no longer recommended.^[5]

Methylene blue is typically given by injection into a vein.^[5] Common side effects include headache, nausea, and vomiting.

Methylene blue was first prepared in 1876, by Heinrich Caro.^[9] It is on the World Health Organization's List of Essential Medicines.^[10]

^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 471. ISBN 978-1-284-05756-0.
^ Cite error: The named reference BNF69 was invoked but never defined (see the help page).
^ Lillie RD (1977). H. J. Conn's Biological stains (9th ed.). Baltimore: Williams & Wilkins. pp. 692p.
^ "Provayblue- methylene blue injection". DailyMed. 29 June 2022. Retrieved 4 March 2023.
^ ^a ^b ^c ^d "Methylene Blue". The American Society of Health-System Pharmacists. Archived from the original on 10 May 2017. Retrieved 8 January 2017.
^ "Lumeblue EPAR". European Medicines Agency. 19 June 2020. Retrieved 4 March 2023.
^ "Lumeblue Product information". Union Register of medicinal products. Retrieved 3 March 2023.
^ Peter C, Hongwan D, Küpfer A, Lauterburg BH (June 2000). "Pharmacokinetics and organ distribution of intravenous and oral methylene blue". European Journal of Clinical Pharmacology. 56 (3): 247–250. doi:10.1007/s002280000124. PMID 10952480.
^ Ahmad I, Aqil F (2008). New Strategies Combating Bacterial Infection. John Wiley & Sons. p. 91. ISBN 978-3-527-62294-8. Archived from the original on 2017-09-18.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[Ric2015-1] Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 471. ISBN 978-1-284-05756-0.

[BNF69-2] Cite error: The named reference BNF69 was invoked but never defined (see the help page).

[Lillie,_1977-3] Lillie RD (1977). H. J. Conn's Biological stains (9th ed.). Baltimore: Williams & Wilkins. pp. 692p.

[Provayblue_FDA_label-4] "Provayblue- methylene blue injection". DailyMed. 29 June 2022. Retrieved 4 March 2023.

[AHFS2017-5] "Methylene Blue". The American Society of Health-System Pharmacists. Archived from the original on 10 May 2017. Retrieved 8 January 2017.

[Lumeblue_EPAR-6] "Lumeblue EPAR". European Medicines Agency. 19 June 2020. Retrieved 4 March 2023.

[7] "Lumeblue Product information". Union Register of medicinal products. Retrieved 3 March 2023.

[pmid10952480-8] Peter C, Hongwan D, Küpfer A, Lauterburg BH (June 2000). "Pharmacokinetics and organ distribution of intravenous and oral methylene blue". European Journal of Clinical Pharmacology. 56 (3): 247–250. doi:10.1007/s002280000124. PMID 10952480.

[Ah2008-9] Ahmad I, Aqil F (2008). New Strategies Combating Bacterial Infection. John Wiley & Sons. p. 91. ISBN 978-3-527-62294-8. Archived from the original on 2017-09-18.

[WHO21st-10] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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