Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:02 UTC
Update Date2014-12-24 20:21:04 UTC
Accession NumberT3D0080
Identification
Common NameDichloromethane
ClassSmall Molecule
DescriptionDichloromethane is used as an extraction solvent in the preparation of decaffeinated coffee, hop extracts and spice oleoresins. Diluent for colour additives and inks for marking fruit and vegetables The output of these processes is a mixture of methyl chloride, dichloromethane, chloroform, and carbon tetrachloride. These compounds are separated by distillation. Dichloromethane has been shown to exhibit anti-tumor, anti-proliferative, analgesic, anti-fungal and antibiotic functions (1, 2, 3, 4, 5). Dichloromethane belongs to the family of Organochlorides. These are organic compounds containing a chlorine atom.
Compound Type
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Aerothene
Aerothene MM
CH2Cl2
DCM
Dichloro-Methane
Distillex DS3
Driverit
Freon 30
M-Clean D
Methane dichloride
Methoklone
Methylene bichloride
Methylene chloride
Methylene dichloride
Narkotil
Nevolin
Salesthin
Solaesthin
Solmethine
Chemical FormulaCH2Cl2
Average Molecular Mass84.933 g/mol
Monoisotopic Mass83.953 g/mol
CAS Registry Number1975-09-02
IUPAC Namedichloromethane
Traditional Namemethylene chloride
SMILESClCCl
InChI IdentifierInChI=1S/CH2Cl2/c2-1-3/h1H2
InChI KeyInChIKey=YMWUJEATGCHHMB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as halomethanes. These are organic compounds in which at least one of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassHalomethanes
Direct ParentHalomethanes
Alternative Parents
Substituents
  • Halomethane
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-96.8°C
Boiling PointNot Available
Solubility13 mg/mL at 25°C
LogP1.25
Predicted Properties
PropertyValueSource
Water Solubility17.5 g/LALOGPS
logP1.12ALOGPS
logP1.29ChemAxon
logS-0.69ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.44 m³·mol⁻¹ChemAxon
Polarizability6.53 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-fea8e21d8ce299fd6c73View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000t-9000000000-3c727a0b79ead1d0afc9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-fea8e21d8ce299fd6c73View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000t-9000000000-3c727a0b79ead1d0afc9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-a20182f85c9e395e5511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-9fdeb81f96b30affd700View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-9fdeb81f96b30affd700View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-9fdeb81f96b30affd700View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-3641e00693a6eab28168View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-3641e00693a6eab28168View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-3641e00693a6eab28168View in MoNA
MSMass Spectrum (Electron Ionization)splash10-000t-9000000000-6ce0b546ffcfe5b5cf7eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (13) ; inhalation (13) ; dermal (13)
Mechanism of ToxicityMethylene chloride targets the lungs, blood system, and nervous system. In the lungs its metabolites damage Clara cells. It is also metabolized into carbon monoxide, which binds to hemoglobin to produce dose-dependent increases in carboxyhemoglobin. This results in the reduced oxygen transport and neurological dysfunction characteristic of carboxyhemoglobinemia (carbon monoxide poisoning). Methylene chloride is also believed to cause neurotoxicity by interfering with signal transmission in a manner similar to general anesthetics. Certain metabolites, such as formaldehyde, may result in carcinogenic effects by causing DNA single strand breaks, DNA-protein crosslinks, and other mutations. (6, 13)
MetabolismAbsorption mainly occurs via inhalation, but may also result from oral or dermal exposure. Methylene chloride is mainly distributed to the adipose tissue and liver. It may be metabolized by cytochrome P-450 2E1, which ultimately produces carbon monoxide and carbon dioxide via formyl chloride. Methylene chloride can also be metabolized by theta glutathione-S-transferase, which produces carbon dioxide via a postulated glutathione conjugate (S-chloromethyl glutathione) and formaldehyde. Both pathways produce toxic metabolites which are excreted mainly in expired air, but also in the urine. (6, 13)
Toxicity ValuesLD50: 437 mg/kg (Intraperitoneal, Mouse) (7) LD50: 6460 mg/kg (Subcutaneous, Mouse) (7) LD50: 1600 mg/kg (Oral, Rat) (8) LC50: 14 400 ppm over 7 hours (Inhalation, Mouse) (7)
Lethal Dose357 mg/kg (oral) or 50 000 ppm (inhalation) for an adult human. (9)
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (12)
Uses/SourcesMethylene chloride is widely used as a solvent in industrial processes, paint stripper, and degreaser. It is also used in food preparation, aerosol propellants, pesticides, and the manufacture of photographic film. (6, 13)
Minimum Risk LevelAcute Inhalation: 0.6 ppm (11) Intermediate Inhalation: 0.3 ppm (11) Chronic Inhalation: 0.3 ppm (11) Acute Oral: 0.2 mg/kg/day (11) Chronic Oral: 0.06 mg/kg/day (11)
Health EffectsExposure to methylene chloride may cause optic neuropathy and hepatitis. Very high concentrations can lead to unconciousness, coma, and death. It is metabolized to carbon monoxide, potentially leading to carbon monoxide poisoning. Methylene chloride also causes liver and kidney injury, and may be a carcinogen. (6, 14)
SymptomsBreathing large amounts of methylene chloride causes dizziness, nausea, tingling or numbness of the finger and toes, loss of concentration, and reduced hand-eye coordination. Very high concentrations can lead to unconciousness, coma, and death. Skin contact with methylene chloride causes burning and redness of the skin. (13, 14)
TreatmentTreatment of methylene chloride exposure is mainly symptomatic. Ingested methylene chloride may be removed by emesis and/or gastric lavage, and activated charcoal. Hyperbaric oxygen may be used to treat the carbon monoxide poisoning that can result from inhalation of methylene chloride. (15)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31548
PubChem Compound ID6344
ChEMBL IDNot Available
ChemSpider ID6104
KEGG IDC02271
UniProt IDNot Available
OMIM ID
ChEBI ID15767
BioCyc IDCPD-4521
CTD IDD008752
Stitch IDMethylene chloride
PDB IDNot Available
ACToR ID885
Wikipedia LinkDichloromethane
References
Synthesis ReferenceNot Available
MSDST3D0080.pdf
General References
  1. Jin W, Shi Q, Hong C, Cheng Y, Ma Z, Qu H: Cytotoxic properties of thiophenes from Echinops grijissi Hance. Phytomedicine. 2008 Sep;15(9):768-74. Epub 2008 Feb 20. [18068965 ]
  2. Barreiro Arcos ML, Cremaschi G, Werner S, Coussio J, Ferraro G, Anesini C: Tilia cordata Mill. Extracts and scopoletin (isolated compound): differential cell growth effects on lymphocytes. Phytother Res. 2006 Jan;20(1):34-40. [16397918 ]
  3. Matheus ME, Berrondo LF, Vieitas EC, Menezes FS, Fernandes PD: Evaluation of the antinociceptive properties from Brillantaisia palisotii Lindau stems extracts. J Ethnopharmacol. 2005 Dec 1;102(3):377-81. Epub 2005 Aug 1. [16076537 ]
  4. Khan MR, Omoloso AD: Antibacterial and antifungal activities of Dracontomelon dao. Fitoterapia. 2002 Jul;73(4):327-30. [12234577 ]
  5. Meyer JJ, Dilika F: Antibacterial activity of Helichrysum pedunculatum used in circumcision rites. J Ethnopharmacol. 1996 Jul 26;53(1):51-4. [8807475 ]
  6. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
  7. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  8. Verschueren K (1983). Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co.
  9. Lewis RJ (2000). Sax's Dangerous Properties of Industrial Materials. 10th ed. New York, NY: Van Nostrand Reinhold Company.
  10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  11. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  12. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  13. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  14. Wikipedia. Dichloromethane. Last Updated 20 May 2009. [Link]
  15. International Programme on Chemical Safety (IPCS) INCHEM (1997). Poison Information Monograph for Methylene Chloride. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:
HBB
Uniprot ID:
P68871
Molecular Weight:
15998.34 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBD
Uniprot ID:
P02042
Molecular Weight:
16055.41 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
Gene Name:
HBE1
Uniprot ID:
P02100
Molecular Weight:
16202.71 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Gene Name:
HBG1
Uniprot ID:
P69891
Molecular Weight:
16140.37 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Specific Function:
Heme binding
Gene Name:
HBG2
Uniprot ID:
P69892
Molecular Weight:
16126.35 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBM
Uniprot ID:
Q6B0K9
Molecular Weight:
15617.97 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBQ1
Uniprot ID:
P09105
Molecular Weight:
15507.575 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
Gene Name:
HBZ
Uniprot ID:
P02008
Molecular Weight:
15636.845 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for methylene chloride. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]