Leucomethylene blue

Base Information

• Chemical Name: Leucomethylene blue
• CAS No.: 613-11-6
• Molecular Formula: C16H19 N3 S
• Molecular Weight: 285.413
• UNII: IHU4GYZ2R3
• DSSTox Substance ID: DTXSID2047985
• Nikkaji Number: J25.657I
• Wikidata: Q27280736
• NCI Thesaurus Code: C170046
• ChEMBL ID: CHEMBL549963
• Mol file: 613-11-6.mol

Synonyms:hydromethylthionine;hydromethylthionine mesylate;leuco-methylthioninium;leucomethylene blue;leukomethylene blue;LMTX compound;Panatone;TRx0237

Chemical Property of Leucomethylene blue

Chemical Property:

• Boiling Point: 491.7±45.0 °C(Predicted)
• PKA: 6.62±0.20(Predicted)
• Flash Point: 251.2oC
• PSA: 43.81000
• Density: 1.201±0.06 g/cm3(Predicted)
• LogP: 4.16480
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 285.12996879
• Heavy Atom Count: 20
• Complexity: 304

Purity/Quality:

98%,99%, ^*data from raw suppliers

LEUCOFORM 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC2=C(C=C1)NC3=C(S2)C=C(C=C3)N(C)C
• General Description: LEUCOFORM (leucomethylene blue) is a reduced form of methylene blue that participates in redox reactions, particularly in the context of antimalarial mechanisms involving artemisinins. The study highlights its role as a redox-active substrate, which artemisinins can oxidize, contributing to the generation of reactive oxygen species (ROS) and disruption of the malaria parasite's redox balance. This interaction underscores LEUCOFORM's relevance in understanding the antimalarial action of artemisinins and their potential to interfere with flavoenzyme function in parasitic redox systems.

Technology Process of Leucomethylene blue

There total 5 articles about Leucomethylene blue which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methylene blue (152071-32-4,105504-42-5,121067-62-7,12262-49-6,167498-52-4,6476-03-5,97130-83-1) + ascorbic acid (50-81-7,98966-42-8) → Leuco-Methylenblau (613-11-6) + L-dehydroascorbic acid (490-83-5)

Guidance literature:

Acidic conditions;

DOI:10.1080/07391102.2018.1559763

Reference yield:

succinic acid (110-15-6) + 3,7-bis(dimethylamine)phenothiazonium (807306-71-4) → Leuco-Methylenblau (613-11-6) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2)

Guidance literature:

das reversibile Gleichgewicht;

Reference yield:

water (7732-18-5) + (4-(2-(thiosulfate)-4-(dimethylamino)-phenylimino)-cyclohex-2,5-dienylidene)-N,N-dimethyl ammonium (15967-15-4) → sulfuric acid (7664-93-9) + Leuco-Methylenblau (613-11-6)

Guidance literature:

upstream raw materials:

succinic acid

3,7-bis(dimethylamine)phenothiazonium

water

(4-(2-(thiosulfate)-4-(dimethylamino)-phenylimino)-cyclohex-2,5-dienylidene)-N,N-dimethyl ammonium

Downstream raw materials:

succinic acid

3,7-bis(dimethylamine)phenothiazonium

methylene blue

leucothionine

Refernces

Facile oxidation of leucomethylene blue and dihydroflavins by artemisinins: Relationship with flavoenzyme function and antimalarial mechanism of action

10.1002/cmdc.201000225

The research investigates the interaction between artemisinins, a class of compounds derived from the plant Artemisia annua and used in the treatment of malaria, and redox-active substrates such as leucomethylene blue and dihydroflavins. The study aims to understand the molecular mechanism by which artemisinins exert their antimalarial effects, particularly their ability to generate reactive oxygen species (ROS) and interfere with the redox balance within the malaria parasite. The researchers found that artemisinins can act as both one-electron transfer agents and two-electron acceptors, potentially disrupting the function of flavin cofactors in redox-active enzymes within the parasite. The chemicals used in the study include artemisinins, methylene blue, ascorbic acid, N-benzyldihydronicotinamide (BNAH), riboflavin, flavin mononucleotide (FMN), and flavin adenine dinucleotide (FAD), among others. The conclusions suggest that artemisinins may act as antimalarial drugs by perturbing the redox balance within the malaria parasite, and their selective potency may be due to differences in sensitivity between parasite and human glutathione reductase. This research provides insights into the potential mechanisms of artemisinin resistance in malaria parasites and could inform the development of new antimalarial drugs.