| Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, sweet-smelling, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant. Most chloromethane is biogenic.
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mutagen
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
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refrigerant
A substance used in a thermodynamic heat pump cycle or refrigeration cycle that undergoes a phase change from a gas to a liquid and back. Refrigerants are used in air-conditioning systems and freezers or refrigerators and are assigned a "R" number (by ASHRAE - formerly the American Society of Heating, Refrigerating and Air Conditioning Engineers), which is determined systematically according to their molecular structure.
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View more via ChEBI Ontology
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CH3Cl
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IUPAC
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chloromethane
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UniProt
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MeCl
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IUPAC
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methyl chloride
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ChemIDplus
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Methylchlorid
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NIST Chemistry WebBook
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methylchloride
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ChemIDplus
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monochloromethane
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ChemIDplus
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R-40
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ChEBI
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1696839
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Reaxys Registry Number
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Reaxys
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24898
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Gmelin Registry Number
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Gmelin
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74-87-3
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CAS Registry Number
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NIST Chemistry WebBook
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74-87-3
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CAS Registry Number
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ChemIDplus
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Ballschmiter K (2003)
Pattern and sources of naturally produced organohalogens in the marine environment: biogenic formation of organohalogens.
Chemosphere 52, 313-324 [PubMed:12738255]
[show Abstract]
The pattern of organohalogens found in the marine environment is complex and includes compounds, only assignable to natural (chloromethane) or anthropogenic (hexachlorobenzene, PCBs) sources as well as compounds of a mixed origin (trichloromethane, halogenated methyl phenyl ether).The chemistry of the formation of natural organohalogens is summarized. The focus is put on volatile compounds carrying the halogens Cl, Br, and I, respectively. Though marine natural organohalogens are quite numerous as defined components, they are mostly not produced as major compounds. The most relevant in terms of global annual production is chloromethane (methyl chloride). The global atmospheric mixing ratio requires an annual production of 3.5-5 million tons per year. The chemistry of the group of haloperoxidases is discussed. Incubation experiments reveal that a wide spectrum of unknown compounds is formed in side reactions by haloperoxidases in pathways not yet understood. | Vaughan P, Lindahl T, Sedgwick B (1993)
Induction of the adaptive response of Escherichia coli to alkylation damage by the environmental mutagen, methyl chloride.
Mutation research 293, 249-257 [PubMed:7679475]
[show Abstract]
Methyl chloride (MeCl) is an abundant environmental mutagen and carcinogen and may be one of several environmental alkylating agents against which the protection of an adaptive response is required in microorganisms. Both MeCl and methyl iodide (MeI), at micromolar concentrations, induced the adaptive response to alkylation damage in Escherichia coli. This response is regulated by the Ada protein which is converted into a transcriptional activator by self-methylation on repair of methylphosphotriesters in methylated DNA. However, using high amounts of Ada protein, activation of Ada occurred in vitro following direct protein methylation by both MeI (in agreement with previously published data) and MeCl. Activation was enhanced when methyl halide treatments were performed in the presence of DNA. An unadapted E. coli cell contains only 2 to 4 molecules of Ada protein, and presents an extremely small target of 2 to 4 specific cysteine residues per cell for activation of Ada by direct protein methylation in vivo. Thus, it is proposed that induction of the adaptive response in vivo initially occurs via efficient repair by the Ada protein of a low number of methylphosphotriesters in DNA. When the cellular Ada protein level has substantially increased, a greater probability of direct methylation and activation of Ada at cysteine-69 by MeCl may sustain and further increase induction of the adaptive response. |
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