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MedKoo Cat#: 100621 | Name: Methylene blue
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methylene blue is a synthetic basic dye. Methylene blue stains to negatively charged cell components like nucleic acids; when administered in the lymphatic bed of a tumor during oncologic surgery, methylene blue may stain lymph nodes draining from the tumor, thereby aiding in the visual localization of tumor sentinel lymph nodes. When administered intravenously in low doses, this agent may convert methemoglobin to hemoglobin.

Chemical Structure

Methylene blue
Methylene blue
CAS#61-73-4 (Cl)

Theoretical Analysis

MedKoo Cat#: 100621

Name: Methylene blue

CAS#: 61-73-4 (Cl)

Chemical Formula: C16H18ClN3S

Exact Mass: 0.0000

Molecular Weight: 319.85

Elemental Analysis: C, 60.08; H, 5.67; Cl, 11.08; N, 13.14; S, 10.02

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
25g USD 450.00 2 weeks
100g USD 750.00 2 weeks
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Related CAS #
61-73-4 (Cl) 7220-79-3 (hydrate)
Synonym
Methylene blue; CI52015.
IUPAC/Chemical Name
3,7-bis(dimethylamino)phenothiazin-5-ium chloride
InChi Key
CXKWCBBOMKCUKX-UHFFFAOYSA-M
InChi Code
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
SMILES Code
CN(C1=CC2=[S+]C3=C(C=CC(N(C)C)=C3)N=C2C=C1)C.[Cl-]
Appearance
Solid powder
Purity
>96% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Methylene blue (CI 52015) is a heterocyclic aromatic chemical compound with the molecular formula C16H18N3SCl. It has many uses in a range of different fields, such as biology and chemistry. At room temperature it appears as a solid, odorless, dark green powder, that yields a blue solution when dissolved in water. The hydrated form has 3 molecules of water per molecule of methylene blue.  Methylene blue should not be confused with methyl blue, another histology stain, new methylene blue, nor with the methyl violets often used as pH indicators. The International Nonproprietary Name (INN) of methylene blue is methylthioninium chloride.    
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methylene blue (Basic Blue 9) is a guanylyl cyclase (sGC), monoamine oxidase A (MAO-A) and NO synthase (NOS) inhibitor. Methylene blue is a vasopressor and is often used as a dye in several medical procedures.
In vitro activity:
MB (methylene blue) reduces mitochondrial superoxide production via alternative electron transfer that bypasses mitochondrial complexes I-III. MB mitigates reactive free radical production and provides neuroprotection in HT-22 cells against glutamate, IAA and rotenone toxicity. Reference: PLoS One. 2012;7(10):e48279. https://pubmed.ncbi.nlm.nih.gov/23118969/
In vivo activity:
Preventive MB (methylene blue) application starting before onset of functional deficits preserved cognition of Tau(ΔK) mice. Beside improved learning and memory, MB-treated Tau(ΔK) mice showed a strong decrease of insoluble Tau, a reduction of conformationally changed (MC1) and phosphorylated Tau species (AT180, PHF1) as well as an upregulation of protein degradation systems (autophagy and proteasome). Reference: Acta Neuropathol Commun. 2015 May 10;3:25. https://pubmed.ncbi.nlm.nih.gov/25958115/
Solvent mg/mL mM comments
Solubility
Water 26.6 83.16
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 319.85 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Poteet E, Winters A, Yan LJ, Shufelt K, Green KN, Simpkins JW, Wen Y, Yang SH. Neuroprotective actions of methylene blue and its derivatives. PLoS One. 2012;7(10):e48279. doi: 10.1371/journal.pone.0048279. Epub 2012 Oct 31. PMID: 23118969; PMCID: PMC3485214. 2. Wen Y, Li W, Poteet EC, Xie L, Tan C, Yan LJ, Ju X, Liu R, Qian H, Marvin MA, Goldberg MS, She H, Mao Z, Simpkins JW, Yang SH. Alternative mitochondrial electron transfer as a novel strategy for neuroprotection. J Biol Chem. 2011 May 6;286(18):16504-15. doi: 10.1074/jbc.M110.208447. Epub 2011 Mar 18. PMID: 21454572; PMCID: PMC3091255. 3. Hochgräfe K, Sydow A, Matenia D, Cadinu D, Könen S, Petrova O, Pickhardt M, Goll P, Morellini F, Mandelkow E, Mandelkow EM. Preventive methylene blue treatment preserves cognition in mice expressing full-length pro-aggregant human Tau. Acta Neuropathol Commun. 2015 May 10;3:25. doi: 10.1186/s40478-015-0204-4. PMID: 25958115; PMCID: PMC4425867. 4. Fenn AM, Skendelas JP, Moussa DN, Muccigrosso MM, Popovich PG, Lifshitz J, Eiferman DS, Godbout JP. Methylene blue attenuates traumatic brain injury-associated neuroinflammation and acute depressive-like behavior in mice. J Neurotrauma. 2015 Jan 15;32(2):127-38. doi: 10.1089/neu.2014.3514. Epub 2014 Nov 13. PMID: 25070744; PMCID: PMC4291210.
In vitro protocol:
1. Poteet E, Winters A, Yan LJ, Shufelt K, Green KN, Simpkins JW, Wen Y, Yang SH. Neuroprotective actions of methylene blue and its derivatives. PLoS One. 2012;7(10):e48279. doi: 10.1371/journal.pone.0048279. Epub 2012 Oct 31. PMID: 23118969; PMCID: PMC3485214. 2. Wen Y, Li W, Poteet EC, Xie L, Tan C, Yan LJ, Ju X, Liu R, Qian H, Marvin MA, Goldberg MS, She H, Mao Z, Simpkins JW, Yang SH. Alternative mitochondrial electron transfer as a novel strategy for neuroprotection. J Biol Chem. 2011 May 6;286(18):16504-15. doi: 10.1074/jbc.M110.208447. Epub 2011 Mar 18. PMID: 21454572; PMCID: PMC3091255.
In vivo protocol:
1. Hochgräfe K, Sydow A, Matenia D, Cadinu D, Könen S, Petrova O, Pickhardt M, Goll P, Morellini F, Mandelkow E, Mandelkow EM. Preventive methylene blue treatment preserves cognition in mice expressing full-length pro-aggregant human Tau. Acta Neuropathol Commun. 2015 May 10;3:25. doi: 10.1186/s40478-015-0204-4. PMID: 25958115; PMCID: PMC4425867. 2. Fenn AM, Skendelas JP, Moussa DN, Muccigrosso MM, Popovich PG, Lifshitz J, Eiferman DS, Godbout JP. Methylene blue attenuates traumatic brain injury-associated neuroinflammation and acute depressive-like behavior in mice. J Neurotrauma. 2015 Jan 15;32(2):127-38. doi: 10.1089/neu.2014.3514. Epub 2014 Nov 13. PMID: 25070744; PMCID: PMC4291210.
1: Frasson M, Faus C, Garcia-Granero A, Puga R, Flor-Lorente B, Cervantes A, Navarro S, Garcia-Granero E. Pathological evaluation of mesocolic resection quality and ex vivo methylene blue injection: what is the impact on lymph node harvest after colon resection for cancer? Dis Colon Rectum. 2012 Feb;55(2):197-204. PubMed PMID: 22228164. 2: Märkl B, Moldovan AI, Jähnig H, Cacchi C, Spatz H, Anthuber M, Oruzio DV, Kretsinger H, Arnholdt HM. Combination of ex vivo sentinel lymph node mapping and methylene blue-assisted lymph node dissection in gastric cancer: a prospective and randomized study. Ann Surg Oncol. 2011 Jul;18(7):1860-8. Epub 2011 Apr 19. PubMed PMID: 21503792. 3: Ceranic MS, Kecmanovic DM, Pavlov MJ, Nale DP, Micev MT, Kovacevic PA, Stamenkovic AB. Validation and feasibility of ex vivo sentinel lymph node "mapping" by methylene blue in colorectal cancer. Hepatogastroenterology. 2010 Sep-Oct;57(102-103):1113-8. PubMed PMID: 21410041. 4: Törnroos A, Shabo I, Druvefors B, Arbman G, Olsson H. Postoperative intra-arterial methylene blue injection of colorectal cancer specimens increases the number of lymph nodes recovered. Histopathology. 2011 Feb;58(3):408-13. doi: 10.1111/j.1365-2559.2011.03755.x. Epub 2011 Feb 16. PubMed PMID: 21323959. 5: Pruthi S, Haakenson C, Brost BC, Bryant K, Reid JM, Singh R, Netzel B, Boughey JC, Degnim AC. Pharmacokinetics of methylene blue dye for lymphatic mapping in breast cancer-implications for use in pregnancy. Am J Surg. 2011 Jan;201(1):70-5. PubMed PMID: 21167367. 6: Xiang J, Xia X, Jiang Y, Leung AW, Wang X, Xu J, Wang P, Yu H, Bai D, Xu C. Apoptosis of ovarian cancer cells induced by methylene blue-mediated sonodynamic action. Ultrasonics. 2011 Apr;51(3):390-5. Epub 2010 Nov 27. PubMed PMID: 21147492. 7: He J, Li S, Shao W, Wang D, Chen M, Yin W, Wang W, Gu Y, Zhong B. Activated carbon nanoparticles or methylene blue as tracer during video-assisted thoracic surgery for lung cancer can help pathologist find the detected lymph nodes. J Surg Oncol. 2010 Nov 1;102(6):676-82. PubMed PMID: 20721962. 8: Jangjoo A, Forghani MN, Mehrabibahar M, Sadeghi R. Anaphylaxis reaction of a breast cancer patient to methylene blue during breast surgery with sentinel node mapping. Acta Oncol. 2010 Aug;49(6):877-8. PubMed PMID: 20429734. 9: Mathelin C, Croce S, Brasse D, Gairard B, Gharbi M, Andriamisandratsoa N, Bekaert V, Francis Z, Guyonnet JL, Huss D, Salvador S, Schaeffer R, Grucker D, Marin C, Bellocq JP. Methylene blue dye, an accurate dye for sentinel lymph node identification in early breast cancer. Anticancer Res. 2009 Oct;29(10):4119-25. PubMed PMID: 19846959. 10: Kerwel TG, Spatz J, Anthuber M, Wünsch K, Arnholdt H, Märkl B. Injecting methylene blue into the inferior mesenteric artery assures an adequate lymph node harvest and eliminates pathologist variability in nodal staging for rectal cancer. Dis Colon Rectum. 2009 May;52(5):935-41. PubMed PMID: 19502859.