Dichloromethane
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Basic Info
| Common Name | Dichloromethane(F03333) |
| 2D Structure | |
| Description | Dichloromethane 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 (A7704, A7705, A7706, A7707, A7708). Dichloromethane belongs to the family of Organochlorides. These are organic compounds containing a chlorine atom. |
| FRCD ID | F03333 |
| CAS Number | 1975-09-02 |
| PubChem CID | 6344 |
| Formula | CH2Cl2 |
| IUPAC Name | dichloromethane |
| InChI Key | YMWUJEATGCHHMB-UHFFFAOYSA-N |
| InChI | InChI=1S/CH2Cl2/c2-1-3/h1H2 |
| Canonical SMILES | C(Cl)Cl |
| Isomeric SMILES | C(Cl)Cl |
| Wikipedia | Dichloromethane |
| Synonyms |
Methylene chloride
Methane dichloride
DICHLOROMETHANE
75-09-2
Methylene dichloride
Methane, dichloro-
Methylene bichloride
Solaesthin
Solmethine
Freon 30
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organohalogen compounds |
| Class | Alkyl halides |
| Subclass | Halomethanes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Halomethanes |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Halomethane - Hydrocarbon derivative - Organochloride - Alkyl chloride - Aliphatic acyclic compound |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 84.927 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 2.8 |
| Monoisotopic Mass | 83.953 |
| Exact Mass | 83.953 |
| XLogP | 1.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 3 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9784 |
| Human Intestinal Absorption | HIA+ | 0.9931 |
| Caco-2 Permeability | Caco2+ | 0.7142 |
| P-glycoprotein Substrate | Non-substrate | 0.9015 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9777 |
| Non-inhibitor | 0.9517 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8630 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4768 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8457 |
| CYP450 2D6 Substrate | Non-substrate | 0.7390 |
| CYP450 3A4 Substrate | Non-substrate | 0.7340 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5990 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8356 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9364 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7254 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9086 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8130 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9254 |
| Non-inhibitor | 0.9659 | |
| AMES Toxicity | AMES toxic | 0.7144 |
| Carcinogens | Carcinogens | 0.8335 |
| Fish Toxicity | Low FHMT | 0.6304 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9042 |
| Honey Bee Toxicity | High HBT | 0.8377 |
| Biodegradation | Not ready biodegradable | 0.6502 |
| Acute Oral Toxicity | III | 0.8205 |
| Carcinogenicity (Three-class) | Warning | 0.4864 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.7930 | LogS |
| Caco-2 Permeability | 1.6274 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9621 | LD50, mol/kg |
| Fish Toxicity | 2.1891 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2885 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| In vitro antiplasmodial, antitrypanosomal and antileishmanial activities of selected medicinal plants from Ugandan flora: Refocusing into multi-component potentials. | J Ethnopharmacol | 2018 Sep 28 | 30273736 |
| Sensitivity enhancement for mycotoxin determination by optical waveguide lightmode spectroscopy using gold nanoparticles of different size and origin. | Food Chem | 2018 Nov 30 | 29934142 |
| Fabrication and characterization of β-cypermethrin-loaded PLA microcapsulesprepared by emulsion-solvent evaporation: loading and release properties. | Environ Sci Pollut Res Int | 2018 May | 29492820 |
| A new sesquiterpene lactone glucoside and other constituents from Inula salsoloides with insecticidal activities on striped flea beetle (Phyllotreta striolata Fabricius). | Nat Prod Res | 2018 Mar | 28562081 |
| Solvent effect on endosulfan adsorption onto polymeric arginine-methacrylatecryogels. | Environ Sci Pollut Res Int | 2018 Jun 27 | 29951763 |
| Antibacterial activity and in situ efficacy of Bidens pilosa Linn and Dichrostachys cinerea Wight et Arn extracts against common diarrhoea-causing waterborne bacteria. | BMC Complement Altern Med | 2018 Jun 1 | 29859076 |
| Volatile and key odourant compounds of Turkish Berberis crataegina fruit usingGC-MS-Olfactometry. | Nat Prod Res | 2018 Apr | 28764557 |
| Single-laboratory validation of an LC-MS/MS method for determining florfenicol(FF) and florfenicol amine (FFA) residues in chicken feathers and application to a residue-depletion study. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2017Apr | 27915584 |
| DLLME-spectrophotometric determination of glyphosate residue in legumes. | Food Chem | 2017 Sep 1 | 28407950 |
| Juncaceae species as sources of innovative bioactive compounds for the foodindustry: In vitro antioxidant activity, neuroprotective properties and in silicostudies. | Food Chem Toxicol | 2017 Sep | 28400325 |
| <i>In Vitro</i> Bioassay-guided Isolation of Radioprotective Fractions from Extracts of <i>Pinus koraiensis</i> Bark. | Pharmacogn Mag | 2017 Oct-Dec | 29200738 |
| Dissipation kinetics, pre-harvest residue limits, and hazard quotient assessmentsof pesticides flubendiamide and fluopicolide in Korean melon (Cucumis melo L.var. makuwa) grown under regulated conditions in plastic greenhouses. | Environ Sci Pollut Res Int | 2017 Oct | 28799066 |
| Antiviral effect of compounds derived from Angelica archangelica L. on Herpessimplex virus-1 and Coxsackievirus B3 infections. | Food Chem Toxicol | 2017 Nov | 28487231 |
| The disappearance rate and risk assessment of thiacloprid residues in Asian pear using liquid chromatography confirmed with tandem mass spectrometry. | Biomed Chromatogr | 2017 May | 27696449 |
| Organochlorine pesticide residues in dried cocoa beans obtained from cocoa storesat Ondo and Ile-Ife, Southwestern Nigeria. | Toxicol Rep | 2017 Mar 6 | 28959635 |
| Toxicity screening of 13 Gambierdiscus strains using neuro-2a and erythrocyte lysis bioassays. | Harmful Algae | 2017 Mar | 28366392 |
| Ultrasound-assisted extraction and solid-phase extraction for the simultaneousdetermination of five amide herbicides in fish samples by gas chromatography withelectron capture detection. | J Sep Sci | 2017 Mar | 28045224 |
| Phytotoxicity Study on Bidens sulphurea Sch. Bip. as a Preliminary Approach forWeed Control. | J Agric Food Chem | 2017 Jun 28 | 28605187 |
| Maitotoxin-4, a Novel MTX Analog Produced by Gambierdiscus excentricus. | Mar Drugs | 2017 Jul 11 | 28696398 |
| A dispersive liquid-liquid microextraction using a switchable polarity dispersivesolvent. Automated HPLC-FLD determination of ofloxacin in chicken meat. | Anal Chim Acta | 2017 Jan 1 | 27876143 |
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
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- 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 ]
- 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
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- 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 ]
- 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
- Mechanism of Action:
- Methylene chloride is 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).
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp14.html
- 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
- Mechanism of Action:
- Methylene chloride is 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).
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp14.html
- 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
- Mechanism of Action:
- Methylene chloride is 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).
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp14.html
- 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
- Mechanism of Action:
- Methylene chloride is 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).
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp14.html
- 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
- Mechanism of Action:
- Methylene chloride is 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).
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp14.html
- General Function:
- Oxygen transporter activity
- Gene Name:
- HBM
- Uniprot ID:
- Q6B0K9
- Molecular Weight:
- 15617.97 Da
- Mechanism of Action:
- Methylene chloride is 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).
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp14.html
- General Function:
- Oxygen transporter activity
- Gene Name:
- HBQ1
- Uniprot ID:
- P09105
- Molecular Weight:
- 15507.575 Da
- Mechanism of Action:
- Methylene chloride is 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).
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp14.html
- 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
- Mechanism of Action:
- Methylene chloride is 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).
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp14.html
- 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
- Mechanism of Action:
- Methylene chloride is 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).
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp14.html