methylene chloride


Summary: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.

Top Publications

  1. Yoon T, Cheon M, Lee A, Lee D, Moon B, Chun J, et al. Anti-inflammatory activity of methylene chloride fraction from Glehnia littoralis extract via suppression of NF-kappa B and mitogen-activated protein kinase activity. J Pharmacol Sci. 2010;112:46-55 pubmed
    ..We investigated the anti-inflammatory effect and inhibitory mechanism on inflammation by the methylene chloride fraction from Glehnia littoralis extract (MCF-GLE), which was more effective than Glehnia littoralis extract ..
  2. Barry K, Zhang Y, Lan Q, Zahm S, Holford T, Leaderer B, et al. Genetic variation in metabolic genes, occupational solvent exposure, and risk of non-hodgkin lymphoma. Am J Epidemiol. 2011;173:404-13 pubmed publisher
    ..77, 95% CI: 1.06, 2.97; P(interaction) = 0.06). In contrast, no effect was observed among AG/GG women. Additional studies with larger sample size are needed to replicate these findings. ..
  3. Kim J, Kim H, Kim S, Park K, Jang H, Lee E, et al. Methylene chloride fraction of the leaves of Thuja orientalis inhibits in vitro inflammatory biomarkers by blocking NF-?B and p38 MAPK signaling and protects mice from lethal endotoxemia. J Ethnopharmacol. 2011;133:687-95 pubmed publisher
    ..7 cells...
  4. Olvera Bello A, Estrada Muñiz E, Elizondo G, Vega L. Susceptibility to the cytogenetic effects of dichloromethane is related to the glutathione S-transferase theta phenotype. Toxicol Lett. 2010;199:218-24 pubmed publisher
    ..DCM was highly cytotoxic in PBMCs, even at doses within the safety range. Due to this toxicity, a review of the maximal limits for occupational exposure to DCM is advised. ..
  5. Cunha W, de Matos G, Souza M, Tozatti M, Andrade e Silva M, Martins C, et al. Evaluation of the antibacterial activity of the methylene chloride extract of Miconia ligustroides, isolated triterpene acids, and ursolic acid derivatives. Pharm Biol. 2010;48:166-9 pubmed publisher
    The methylene chloride extract of Miconia ligustroides (DC...
  6. Pang Q, Dou L, Pan X, Zeng S, He J, Xu W, et al. Methylene chloride protects against cecal ligation and puncture-induced acute lung injury by modulating inflammatory mediators. Int Immunopharmacol. 2010;10:929-32 pubmed publisher
    ..In this study, we assessed the role of CO donor, methylene chloride (MC), on modulation of lung inflammation during sepsis...
  7. Lee E, Harper M, Bowen R, Slaven J. Evaluation of COSHH essentials: methylene chloride, isopropanol, and acetone exposures in a small printing plant. Ann Occup Hyg. 2009;53:463-74 pubmed publisher
    ..Historically, collected time-weighted average concentrations (seven results) were evaluated for methylene chloride. The COSHH Essentials model recommended general ventilation control for both isopropanol and acetone...
  8. Nguelefack Mbuyo P, Nguelefack T, Dongmo A, Afkir S, Azebaze A, Dimo T, et al. Anti-hypertensive effects of the methanol/methylene chloride stem bark extract of Mammea africana in l-NAME-induced hypertensive rats. J Ethnopharmacol. 2008;117:446-50 pubmed publisher
    The methanol/methylene chloride (CH(3)OH/CH(2)Cl(2)) extract from the stem bark of Mammea africana was showed to possess vasodilating effect in the presence and the absence of N(omega)-nitro-l-arginine methyl ester (l-NAME)...
  9. Nagai E, Otani K, Satoh Y, Suzuki S. Repair of denture base resin using woven metal and glass fiber: effect of methylene chloride pretreatment. J Prosthet Dent. 2001;85:496-500 pubmed
    ..Autopolymerizing acrylic resin was used with woven metal fiber and glass fiber with and without methylene chloride surface treatment (n = 6 per group)...

More Information


  1. Dimo T, Azay J, Tan P, Pellecuer J, Cros G, Bopelet M, et al. Effects of the aqueous and methylene chloride extracts of Bidens pilosa leaf on fructose-hypertensive rats. J Ethnopharmacol. 2001;76:215-21 pubmed
    We investigated the effects of the aqueous (150-350 mg/kg) and methylene chloride (150-300 mg/kg) extracts of Bidens pilosa on fructose-induced hypertension in rats...
  2. Enander R, Cohen H, Gute D, Brown L, Desmaris A, Missaghian R. Lead and methylene chloride exposures among automotive repair technicians. J Occup Environ Hyg. 2004;1:119-25 pubmed
    ..have shown that automotive repair technicians may be exposed to metal particulates in sanding dust and methylene chloride vapors during vehicle paint removal operations...
  3. Demarini D, Shelton M, Warren S, Ross T, Shim J, Richard A, et al. Glutathione S-transferase-mediated induction of GC-->AT transitions by halomethanes in Salmonella. Environ Mol Mutagen. 1997;30:440-7 pubmed
    ..The implications of these findings are discussed in relation to previous experimental work on the GST-mediated bioactivation of dihalomethanes, which includes the possible formation of GSH intermediates and/or GSH-DNA adducts. ..
  4. Kamtchouing P, Kahpui S, Dzeufiet P, Tedong L, Asongalem E, Dimo T. Anti-diabetic activity of methanol/methylene chloride stem bark extracts of Terminalia superba and Canarium schweinfurthii on streptozotocin-induced diabetic rats. J Ethnopharmacol. 2006;104:306-9 pubmed
    ..The anti-diabetic effects of the methanol/methylene chloride extracts of the stem barks on streptozotocin (STZ)-induced diabetes were evaluated on male rats...
  5. Mainwaring G, Williams S, Foster J, Tugwood J, Green T. The distribution of theta-class glutathione S-transferases in the liver and lung of mouse, rat and human. Biochem J. 1996;318 ( Pt 1):297-303 pubmed
    ..the cellular and sub-cellular distribution within the liver and lungs of each species, provides an explanation for the species-specificity of methylene chloride, a mouse-specific carcinogen activated by glutathione S-transferase GSTT1-1.
  6. Graves R, Trueman P, Jones S, Green T. DNA sequence analysis of methylene chloride-induced HPRT mutations in Chinese hamster ovary cells: comparison with the mutation spectrum obtained for 1,2-dibromoethane and formaldehyde. Mutagenesis. 1996;11:229-33 pubmed
    Glutathione-S-transferase-mediated metabolism of methylene chloride (MC) generates S-chloromethylglutathione, which has the potential to react with DNA, and formaldehyde, which is a known mutagen...
  7. Graves R, Callander R, Green T. The role of formaldehyde and S-chloromethylglutathione in the bacterial mutagenicity of methylene chloride. Mutat Res. 1994;320:235-43 pubmed
    b>Methylene chloride was less mutagenic in Salmonella typhimurium TA100/NG-11 (glutathione-deficient) compared to TA100, indicating that glutathione is involved in the activation of methylene chloride to a mutagen in bacteria...
  8. Dimo T, Rakotonirina S, Tan P, Azay J, Dongo E, Kamtchouing P, et al. Effect of Sclerocarya birrea (Anacardiaceae) stem bark methylene chloride/methanol extract on streptozotocin-diabetic rats. J Ethnopharmacol. 2007;110:434-8 pubmed
    ..The stem bark methanol/methylene chloride extract of Sclerocarya birrea exhibited at termination, a significant reduction in blood glucose and ..
  9. Bos P, Zeilmaker M, van Eijkeren J. Application of physiologically based pharmacokinetic modeling in setting acute exposure guideline levels for methylene chloride. Toxicol Sci. 2006;91:576-85 pubmed
    ..In the AEGL setting for methylene chloride, specific additional topics had to be addressed...
  10. Lee E, Lee J, Kim K, Baek N, Lee S, Lee B, et al. The methylene chloride fraction of Trichosanthis Fructus induces apoptosis in U937 cells through the mitochondrial pathway. Biol Pharm Bull. 2006;29:21-5 pubmed
    ..In the present study, the apoptotic mechanism of the methylene chloride fraction of Trichosanthis Fructus (MCTF) was investigated in human leukemic U937 cells...
  11. Cha Y, Lee E, Lee H, Park Y, Ko S, Kim D, et al. Methylene chloride fraction of Scutellaria barbata induces apoptosis in human U937 leukemia cells via the mitochondrial signaling pathway. Clin Chim Acta. 2004;348:41-8 pubmed
    ..Scutellaria barbata D.Don has been applied to treat cancers, inflammation and urinary disease. However, its antitumor mechanism still remains unclear...
  12. Sherratt P, Williams S, Foster J, Kernohan N, Green T, Hayes J. Direct comparison of the nature of mouse and human GST T1-1 and the implications on dichloromethane carcinogenicity. Toxicol Appl Pharmacol. 2002;179:89-97 pubmed
    ..Taking this information into account, it is unlikely that humans have a sufficiently high capacity to activate DCM for this compound to be considered to represent a carcinogenic risk. ..
  13. Sah H. Protein behavior at the water/methylene chloride interface. J Pharm Sci. 1999;88:1320-5 pubmed
    The objective of this study was to investigate the behaviors of proteins at the water/methylene chloride interface to better understand denaturing effects of emulsification upon proteins...
  14. Sah H. Stabilization of proteins against methylene chloride/water interface-induced denaturation and aggregation. J Control Release. 1999;58:143-51 pubmed
    The purpose of this study was to stabilize proteins during the commonly used microencapsulation process of methylene chloride/water emulsification...
  15. Graves R, Green T. Mouse liver glutathione S-transferase mediated metabolism of methylene chloride to a mutagen in the CHO/HPRT assay. Mutat Res. 1996;367:143-50 pubmed
    Although methylene chloride (MC) is readily detectable as a bacterial mutagen, published studies in mammalian cells have been inconclusive. We have previously shown (Graves et al...
  16. Riley D, Small M, Fischhoff B. Modeling methylene chloride exposure-reduction options for home paint-stripper users. J Expo Anal Environ Epidemiol. 2000;10:240-50 pubmed
    ..Paint stripping is of particular concern because of the high potential exposures to methylene chloride, a solvent that is a potential human carcinogen and neurotoxicant...
  17. Chitsazi M, Korbekandi H, Asghari G, Bahri Najafi R, Badii A, Iravani S. Synthesis of silver nanoparticles using methanol and dichloromethane extracts of Pulicaria gnaphalodes (Vent.) Boiss. aerial parts. Artif Cells Nanomed Biotechnol. 2016;44:328-33 pubmed publisher
    ..Methanol extract of this plant seems to be quiet useful for industrial scale production of nanoparticles. ..
  18. Chen D, Ouyang D, Liu H, Chen J, Zhuang Q, Chen J. Effective utilization of dichloromethane by a newly isolated strain Methylobacterium rhodesianum H13. Environ Sci Pollut Res Int. 2014;21:1010-9 pubmed publisher
    ..55 to 3.02) though a buffer system was employed. ..
  19. Marín Loaiza J, Nieto Camacho A, Cespedes C. Antioxidant and anti-inflammatory activities of Pittocaulon species from México. Pharm Biol. 2013;51:260-6 pubmed publisher
    ..Additional studies must be done to identify the compounds responsible of the activity on these plants and to establish the mechanism of action. ..
  20. Hadad G, Badr J, El Nahriry K, Hassanean H. Validated HPLC and HPTLC methods for simultaneous determination of colchicine and khellin in pharmaceutical formulations. J Chromatogr Sci. 2013;51:258-65 pubmed publisher
    ..separation was conducted on Merck HPTLC aluminum sheets of silica gel 60 F254 as stationary phase using methylene chloride-methanol (95:5 v/v) as a mobile phase...
  21. Whitfield D. Plausible Transition States for glycosylation reactions. Carbohydr Res. 2012;356:180-90 pubmed publisher
    ..These hypothetical models are intended to guide both experimental and computational approaches to finding TSs for glycosylation reactions that can be used to optimize stereoselectivity of glycosylation. ..
  22. Chen Y, Cai S, Cai C, Cui X, Chen Z. High-resolution NMR spectroscopy in inhomogeneous fields via Hadamard-encoded intermolecular double-quantum coherences. NMR Biomed. 2012;25:1088-94 pubmed publisher
    ..This method may provide a promising technique for applications in in vivo and in vitro NMR. ..
  23. Justicia Leon S, Ritalahti K, Mack E, Löffler F. Dichloromethane fermentation by a Dehalobacter sp. in an enrichment culture derived from pristine river sediment. Appl Environ Microbiol. 2012;78:1288-91 pubmed publisher
    ..DCM was not reductively dechlorinated, and acetate was produced, indicating DCM fermentation and further suggesting Dehalobacter growth is not limited to organohalide respiration. ..
  24. Lu M, Zhang Z, Qiao W, Wei X, Guan Y, Ma Q, et al. Remediation of petroleum-contaminated soil after composting by sequential treatment with Fenton-like oxidation and biodegradation. Bioresour Technol. 2010;101:2106-13 pubmed publisher
    ..The number of compounds containing two oxygen atoms dropped from 604 to 163 during Fenton-like oxidation, and increased again to 577 after biodegradation. ..
  25. Chin Y, Jung H, Chai H, Keller W, Kinghorn A. Xanthones with quinone reductase-inducing activity from the fruits of Garcinia mangostana (Mangosteen). Phytochemistry. 2008;69:754-8 pubmed
    ..Of these, compounds 1-4 induced quinone reductase (concentration to double enzyme induction, 0.68-2.2microg/mL) in Hepa 1c1c7 cells and gamma-mangostin (6) exhibited hydroxyl radical-scavenging activity (IC50, 0.20microg/mL)...
  26. Iwamoto H, Mizutani T, Kano K. Thermodynamics of hydrophobic interactions: entropic recognition of a hydrophobic moiety by poly(ethylene oxide)-zinc porphyrin conjugates. Chem Asian J. 2007;2:1267-75 pubmed
    ..The binding affinity was modulated by the addition of cations and by varying the degree of polymerization of poly(ethylene oxide), which suggests that guest binding is coupled with polymer conformation. ..
  27. Freire C, Silvestre A, Neto C. Demonstration of long-chain n-alkyl caffeates and delta7-steryl glucosides in the bark of Acacia species by gas chromatography-mass spectrometry. Phytochem Anal. 2007;18:151-6 pubmed
  28. Franco P, Zhang T. Common approaches for efficient method development with immobilised polysaccharide-derived chiral stationary phases. J Chromatogr B Analyt Technol Biomed Life Sci. 2008;875:48-56 pubmed publisher
    ..The rational combination of both modes leads to efficient approaches to get enantiomeric resolutions in reasonable time frames and with high success rates. ..
  29. Yenisey M, Kulunk S. Effects of chemical surface treatments of quartz and glass fiber posts on the retention of a composite resin. J Prosthet Dent. 2008;99:38-45 pubmed publisher
    ..The purpose of this study was to evaluate the effect of 2 chemical solvents, hydrogen peroxide and methylene chloride, on the shear bond strength of quartz and glass fiber posts to a composite resin. Twenty-four posts (3 +/-0...
  30. Unger C, Popescu R, Giessrigl B, Laimer D, Heider S, Seelinger M, et al. The dichloromethane extract of the ethnomedicinal plant Neurolaena lobata inhibits NPM/ALK expression which is causal for anaplastic large cell lymphomagenesis. Int J Oncol. 2013;42:338-48 pubmed publisher
    ..The discovery of the 'Active Principle(s)' is warranted. ..
  31. Nirogi R, Kandikere V, Komarneni P, Aleti R, Padala N, Kalaikadiban I. Quantification of cinacalcet by LC-MS/MS using liquid-liquid extraction from 50 ?L of plasma. J Pharm Biomed Anal. 2011;56:373-81 pubmed publisher
    ..Following oral administration the maximum mean concentration in plasma (C(max); 160±56 ng/mL) was achieved at 1.0 h (T(max)), area under the curve (AUC) and half-life (t(½)) were 949±257 ng h/mL and 3.58±0.4 h, respectively. ..
  32. Korkmaz T, Dogan A, Dogan O, Demir H. The bond strength of a highly cross-linked denture tooth to denture base polymers: a comparative study. J Adhes Dent. 2011;13:85-92 pubmed publisher
  33. McDermott C, Heffron J. Toxicity of industrially relevant chlorinated organic solvents in vitro. Int J Toxicol. 2013;32:136-45 pubmed publisher
    ..However, increased ROS formation did play a causal role in the decreased cell proliferation observed. ..
  34. Umadevi M, Vanelle P, Terme T, Rajkumar B, Ramakrishnan V. Spectral investigations of solvatochromism and preferential solvation on 1,4-dihydroxy-2,3-dimethyl-9,10-anthraquinone. J Fluoresc. 2008;18:1139-49 pubmed publisher
    ..In the case of DMF+dichloromethane mixture DHDMAQ is preferentially solvated by DMF. ..
  35. Kavanagh S, Piccinini A, Connon S. The asymmetric synthesis of terminal aziridines by methylene transfer from sulfonium ylides to imines. Org Biomol Chem. 2013;11:3535-40 pubmed publisher
  36. Bai C, SHI X, Liu D, Li S. [Study on the chemical constituent from the dichloromethane extract of the pine needle of Cedrus deodara (II)]. Zhong Yao Cai. 2013;36:567-9 pubmed
    ..Compounds 1 - 4, 6 and 7 are isolated from this plant for the first time. ..
  37. Flores J, Díaz A, Fernández de Córdova M. Determination of azoxystrobin residues in grapes, musts and wines with a multicommuted flow-through optosensor implemented with photochemically induced fluorescence. Anal Chim Acta. 2007;585:185-91 pubmed
    ..0-87.6%, 95.5-105.9% and 88.5-111.2%, respectively. The quantification limit for grapes was 0.021 mg Kg(-1), being within European Union regulations, and 18 microg L(-1) and 8 microg L(-1) for must and wine, respectively. ..
  38. Cayot N, Lafarge C, Bou Maroun E, Cayot P. Substitution of carcinogenic solvent dichloromethane for the extraction of volatile compounds in a fat-free model food system. J Chromatogr A. 2016;1456:77-88 pubmed publisher
    ..Mixtures of solvents such as azeotrope propan-2-one/cyclopentane, azeotrope ethyl acetate/ethanol, and mixture ethyl acetate/ethanol (3:1, v/v) gave higher extraction yields than those obtained with dichloromethane. ..
  39. Taluja A, Bae Y. Role of a novel multifunctional excipient poly(ethylene glycol)-block-oligo(vinyl sulfadimethoxine) in controlled release of lysozyme from PLGA microspheres. Int J Pharm. 2008;358:50-9 pubmed publisher
    ..Manipulation of such polyelectrolyte-protein complexation may play a role in protein-controlled delivery. ..
  40. Chen C, Chen C, Ong T. Complementary helicity interchange of optically switchable supramolecular-enantiomeric helicenes with (-)-gel-sol-(+)-gel transition ternary logic. J Am Chem Soc. 2013;135:5294-7 pubmed publisher
    ..The helicenes undergo excellent complementary photoswitchings of ternary logic at 280, 318, and 343 nm through (-)-gel-sol-(+)-gel interconversion. ..
  41. Wang Y, Zhou J, Tang Y, Wei Y, Gong H, Li X, et al. Nanocomplexation-assisted solubilization of pDNA in organic solvents for improved microencapsulation. J Colloid Interface Sci. 2013;394:573-81 pubmed publisher
    ..This complexation mediated pDNA solubilization in organic solvents may facilitate the development of novel nano- and micro-platforms for gene delivery. ..
  42. Noufou O, Wamtinga S, André T, Christine B, Marius L, Emmanuelle H, et al. Pharmacological properties and related constituents of stem bark of Pterocarpus erinaceus Poir. (Fabaceae). Asian Pac J Trop Med. 2012;5:46-51 pubmed publisher
  43. Rocha O, de Felício R, Rodrigues A, Ambrósio D, Cicarelli R, de Albuquerque S, et al. Chemical profile and biological potential of non-polar fractions from Centroceras clavulatum (C. Agardh) Montagne (Ceramiales, Rhodophyta). Molecules. 2011;16:7105-14 pubmed publisher
    ..cruzi forms (epimastigote IC(50) = 19.1 ?g.mL-1 and trypomastigote IC(50) = 76.2 ?g.mL-1). The hexanes and ethyl acetate fractions also displayed activity against both fungi species (200 ?g) by TLC-bioautography. ..
  44. Debgupta J, Kakade B, Pillai V. Competitive wetting of acetonitrile and dichloromethane in comparison to that of water on functionalized carbon nanotube surfaces. Phys Chem Chem Phys. 2011;13:14668-74 pubmed publisher
    ..Ozone treatment has been observed to affect the surface properties of pristine CNTs along with a concomitant change in the wetting dynamics. ..
  45. Zalewski C, Passero L, Melo A, Corbett C, Laurenti M, Toyama M, et al. Evaluation of anti-inflammatory activity of derivatives from aerial parts of Baccharis uncinella. Pharm Biol. 2011;49:602-7 pubmed publisher
    ..To date, the present work describes for the first time the anti-inflammatory effects of compounds isolated from B. uncinella. ..
  46. Pisani E, Fattal E, Paris J, Ringard C, Rosilio V, Tsapis N. Surfactant dependent morphology of polymeric capsules of perfluorooctyl bromide: influence of polymer adsorption at the dichloromethane-water interface. J Colloid Interface Sci. 2008;326:66-71 pubmed publisher
    ..When the surfactant rearrangement at the interface is long (>30 min), a coexistence of morphologies can be obtained. ..
  47. De Pinho P, Gonçalves R, Valentão P, Pereira D, Seabra R, Andrade P, et al. Volatile composition of Catharanthus roseus (L.) G. Don using solid-phase microextraction and gas chromatography/mass spectrometry. J Pharm Biomed Anal. 2009;49:674-85 pubmed publisher
    ..Dichloromethane extraction allowed also the identification of some alkaloid-like compounds that were not detected by HS-SPME. ..
  48. Serrilli A, Graziosi V, Ballero M, Foddis C, Serafini M, Poli F, et al. Endemic Sardinian plants: the case of Genista cadasonensis Valsecchi. Nat Prod Res. 2010;24:942-7 pubmed publisher
    ..The antioxidant activity of dichloromethanic, ethanolic and acetonic total extracts of aerial parts was evaluated...
  49. Shimizu H, Kawaguchi T, Yoshida K, Tsue F, Takahashi Y. Effect of surface preparation on the failure load of a highly filled composite resin bonded to a denture base resin. J Prosthodont. 2009;18:684-7 pubmed publisher
    ..The purpose of this study was to evaluate the effect of the surface preparation on the maximum fracture load value of a highly filled gingival shade composite resin bonded to a denture base resin...
  50. Atsbeha T, Mohammed A, Redi Abshiro M. Excitation wavelength dependence of dual fluorescence of DMABN in polar solvents. J Fluoresc. 2010;20:1241-8 pubmed publisher
  51. Yang E, Moon J, Lee J, Koh J, Lee N, Hyun C. Acanthopanax koreanum fruit waste inhibits lipopolysaccharide-induced production of nitric oxide and prostaglandin E2 in RAW 264.7 macrophages. J Biomed Biotechnol. 2010;2010:715739 pubmed publisher
    ..In these tests, AFW extracts did not induce any adverse reactions. Based on these results, we suggest that AFW extracts be considered possible anti-inflammatory candidates for topical application. ..
  52. Kahnt A, Heiniger L, Liu S, Tu X, Zheng Z, Hauser A, et al. An electrochemical and photophysical study of a covalently linked inorganic-organic dyad. Chemphyschem. 2010;11:651-8 pubmed publisher
    ..A light-induced electron transfer between the inorganic cluster moiety and the fullerene can be excluded. However, a light-induced energy transfer from the rhenium cluster to the fullerene is proposed. ..
  53. Okusa P, Penge O, Devleeschouwer M, Duez P. Direct and indirect antimicrobial effects and antioxidant activity of Cordia gilletii De Wild (Boraginaceae). J Ethnopharmacol. 2007;112:476-81 pubmed
    ..2 and 8.1 microg/ml, respectively. These results support the use of the plant in the treatment of infectious diseases and wounds; they warrant further studies as to the nature of active compounds...