Record Information |
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Version | 2.0 |
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Creation Date | 2009-03-06 18:58:04 UTC |
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Update Date | 2014-12-24 20:21:06 UTC |
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Accession Number | T3D0097 |
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Identification |
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Common Name | 1,1,1-Trichloroethane |
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Class | Small Molecule |
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Description | 1,1,1-Trichloroethane is generally considered as a polar solvent. Owing to its unsymmetrical structure, it is a superior solvent for organic compounds that do not dissolve well in hydrocarbons such as hexane. It is an excellent solvent for many organic materials and also one of the least toxic of the chlorinated hydrocarbons. Prior to the Montreal Protocol, it was widely used for cleaning metal parts and circuit boards, as a photoresist solvent in the electronics industry, as an aerosol propellant, as a cutting fluid additive, and as a solvent for inks, paints, adhesives and other coatings. 1,1,1-Trichloroethane is marketed with stabilizers since it is unstable with respect to dehydrochlorination and attacks some metals. Stabilizers comprise up to 8% of the formulation, including acid scavengers (epoxides, amines) and complexants. The Montreal Protocol targeted 1,1,1-trichloroethane as one of those compounds responsible for ozone depletion and banned its use beginning in 1996. Since then, its manufacture and use has been phased out throughout most of the world. The organic compound 1,1,1-trichloroethane, also known as methyl chloroform, is a chloroalkane. This colourless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and its use is being rapidly phased out. |
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Compound Type | - Food Toxin
- Household Toxin
- Industrial/Workplace Toxin
- Metabolite
- Organic Compound
- Organochloride
- Pollutant
- Solvent
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 1,1,1 Trichloroethane | 1,1,1-TCE | 1,1,1-Trichloraethan | 1,1,1-Trichlorathan | 1,1,1-Trichlorethane | 1,1,1-Trichloro-2-(O-chlorophenyl)-2-(p-chlorophenyl)ethane | 1,1,1-Trichloro-Ethane | 1,1,1-Tricloroetano | 2-(2-Chlorophenyl)-2-(4-chlorophenyl)-1,1,1-trichloroethane | Aerothene TT | alpha-T | alpha-Trichloroethane | CH3CCl3 | Chlorotene | Chlorothane NU | Chlorothene | Chlorten | Cleanite | Distillex DS1 | Ethana | Ethana NU | Genklene LB | ICI-CF 2 | Inhibisol | Methyl-Chloroform | Methylchloroform | Methyltrichloromethane | Solvethane | Tafclean | Tri-ethane | Trichloro-1,1,1-ethane | Trichloroethane | Trichloromethylmethane |
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Chemical Formula | C2H3Cl3 |
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Average Molecular Mass | 133.404 g/mol |
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Monoisotopic Mass | 131.930 g/mol |
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CAS Registry Number | 71-55-6 |
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IUPAC Name | 1,1,1-trichloroethane |
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Traditional Name | trichloroethane |
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SMILES | CC(Cl)(Cl)Cl |
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InChI Identifier | InChI=1S/C2H3Cl3/c1-2(3,4)5/h1H3 |
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InChI Key | InChIKey=UOCLXMDMGBRAIB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as organochlorides. Organochlorides are compounds containing a chemical bond between a carbon atom and a chlorine atom. |
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Kingdom | Organic compounds |
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Super Class | Organohalogen compounds |
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Class | Organochlorides |
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Sub Class | Not Available |
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Direct Parent | Organochlorides |
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Alternative Parents | |
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Substituents | - Hydrocarbon derivative
- Organochloride
- Alkyl halide
- Alkyl chloride
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | Not Available |
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Chemical Roles | |
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Physical Properties |
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State | Liquid |
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Appearance | Colorless liquid. |
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Experimental Properties | Property | Value |
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Melting Point | -30.4°C | Boiling Point | 74 °C (347°K, 165 °F) | Solubility | 1.29 mg/mL at 25°C | LogP | 2.49 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-9000000000-acdd1de2f2f494cc9f33 | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-9100000000-93c8b64bf9a3e2f74a6d | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-0002-9100000000-756b9bd2a76d828e0d45 | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-9000000000-acdd1de2f2f494cc9f33 | 2018-05-18 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-9100000000-93c8b64bf9a3e2f74a6d | 2018-05-18 | View Spectrum | GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-0002-9100000000-756b9bd2a76d828e0d45 | 2018-05-18 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000t-9600000000-c081dcbb807720cca52e | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-e0c9bb24f0f03e2e03d6 | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-e0c9bb24f0f03e2e03d6 | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-2900000000-86949d54288e0f2f7c23 | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-069dedae972a3a56c2ff | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-1900000000-6dca5faa37b128ac40a7 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100000000-53cbfa180588956738d7 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-c8f6da92e011fc99d023 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-c8f6da92e011fc99d023 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-9000000000-764e8b6db288ec387c28 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-6838b4c597e6d80ac4e2 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-6838b4c597e6d80ac4e2 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-0900000000-6838b4c597e6d80ac4e2 | 2021-09-24 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0002-9100000000-09ba0e8b7b22dd786338 | 2014-09-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Oral (19); inhalation (19) ; dermal (19) |
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Mechanism of Toxicity | 1,1,1-Trichloroethane is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. |
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Metabolism | Upon first exposure, 1,1,1-trichloroethane is rapidly and efficiently absorbed by the lung, skin, and gastrointestinal tract of humans. 1,1,1-Trichloroethane is distributed by the blood to tissues and organs throughout the body, including to developing fetuses, with preferential distribution to fatty tissues. The predominant pathway of elimination of 1,1,1-trichloroethane in humans, regardless of route of exposure, is exhalation of the unchanged compound. 1,1,1-Trichloroethane is metabolized oxidatively, at low rates, to trichloroethanol and trichloroacetic acid by the cytochrome P-450 mixed-function oxidase system. These metabolites are excreted in the urine, and other minor metabolites (carbon dioxide [CO2] and acetylene) are excreted in expired air. (17) |
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Toxicity Values | LD50: 11 240 mg/kg (Oral, Mouse) (17)
LD50: 9470 mg/kg (Oral, Guinea pig) (17)
LD50: 5660 mg/kg (Oral, Rabbit) (17) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (20) |
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Uses/Sources | 1,1,1-Trichloroethane was often used as a solvent to dissolve other substances, such as glues and paints. In industry, it was widely used to remove oil or grease from manufactured parts. In the home, it is used as an ingredient of products such as spot cleaners, glues, and aerosol sprays. No 1,1,1-trichloroethane is supposed to be manufactured for domestic use in the United States after January 1, 2002, because it affects the ozone layer. Exposure can occur from breathing in air containing it in vapor form, drinking water or eating food containing 1,1,1-trichloroethane. (17) |
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Minimum Risk Level | Acute Inhalation: 2 ppm (17)
Intermediate Inhalation: 0.7 ppm (Gerbil) (17)
Intermediate Oral: 20 mg/kg/day (Mouse) (17) |
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Health Effects | Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides. |
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Symptoms | Symptoms include cough, sore throat, headache, dizziness, drowsiness, nausea, ataxia, unconsciousness. Dry skin and redness follow dermal exposure, while nausea, vomiting, abdominal pain, and diarrhoea follw ingestion. (19) |
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Treatment | If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB41791 |
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PubChem Compound ID | 6278 |
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ChEMBL ID | CHEMBL16080 |
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ChemSpider ID | 6042 |
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KEGG ID | C18246 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 36015 |
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BioCyc ID | CPD-8985 |
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CTD ID | Not Available |
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Stitch ID | 1,1,1-Trichloroethane |
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PDB ID | Not Available |
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ACToR ID | 1413 |
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Wikipedia Link | 1,1,1-trichloroethane |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D0097.pdf |
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General References | - Casciola LA, Ivanetich KM: Metabolism of chloroethanes by rat liver nuclear cytochrome P-450. Carcinogenesis. 1984 May;5(5):543-8. [6722974 ]
- He Z, Yang GP, Lu XL: Distributions and sea-to-air fluxes of volatile halocarbons in the East China Sea in early winter. Chemosphere. 2013 Jan;90(2):747-57. doi: 10.1016/j.chemosphere.2012.09.067. Epub 2012 Oct 25. [23102696 ]
- Pohland R, Tiemann U: Forskolin-induced cyclic AMP signaling in single adherent bovine oviductal cells: effect of dichlorodiphenyltrichloroethane (DDT) and tris(4-chlorophenyl)methanol (TCPM). Toxicol In Vitro. 2003 Jun;17(3):375-83. [12781216 ]
- Brown TJ, Blaustein JD: 1-(o-Chlorophenyl)-1 (p-chlorophenyl)2,2,2-trichloroethane induces functional progestin receptors in the rat hypothalamus and pituitary gland. Endocrinology. 1984 Dec;115(6):2052-8. [6499760 ]
- Steinmetz R, Young PC, Caperell-Grant A, Gize EA, Madhukar BV, Ben-Jonathan N, Bigsby RM: Novel estrogenic action of the pesticide residue beta-hexachlorocyclohexane in human breast cancer cells. Cancer Res. 1996 Dec 1;56(23):5403-9. [8968093 ]
- Palanza P, Morellini F, Parmigiani S, vom Saal FS: Prenatal exposure to endocrine disrupting chemicals: effects on behavioral development. Neurosci Biobehav Rev. 1999 Nov;23(7):1011-27. [10580314 ]
- Noriega NC, Hayes TB: DDT congener effects on secondary sex coloration in the reed frog Hyperolius argus: a partial evaluation of the Hyperolius argus endocrine screen. Comp Biochem Physiol B Biochem Mol Biol. 2000 Jun;126(2):231-7. [10874170 ]
- Legler J, van den Brink CE, Brouwer A, Murk AJ, van der Saag PT, Vethaak AD, van der Burg B: Development of a stably transfected estrogen receptor-mediated luciferase reporter gene assay in the human T47D breast cancer cell line. Toxicol Sci. 1999 Mar;48(1):55-66. [10330684 ]
- Bulger WH, Muccitelli RM, Kupfer D: Interactions of chlorinated hydrocarbon pesticides with the 8S estrogen-binding protein in rat testes. Steroids. 1978 Sep;32(2):165-77. [715816 ]
- Bulger WH, Kupfer D: Inhibition of the 1-(o-chlorophenyl)-1-(p-chlorophenyl)-2,2,2-trichloroethane (o,p'DDT)- and estradiol-mediated induction of rat uterine ornithine decarboxylase by prior treatment with o,p'DDT estradiol, and tamoxifen. Arch Biochem Biophys. 1977 Jul;182(1):138-46. [883826 ]
- Alawi MA, Ammari N, al-Shuraiki Y: Organochlorine pesticide contaminations in human milk samples from women living in Amman, Jordan. Arch Environ Contam Toxicol. 1992 Aug;23(2):235-9. [1514844 ]
- Palanza P, Parmigiani S, vom Saal FS: Effects of prenatal exposure to low doses of diethylstilbestrol, o,p'DDT, and methoxychlor on postnatal growth and neurobehavioral development in male and female mice. Horm Behav. 2001 Sep;40(2):252-65. [11534990 ]
- Kupfer D, Bulger WH: A novel in vitro method for demonstrating proestrogens. Metabolism of methoxychlor and o,p'DDT by liver microsomes in the presence of uteri and effects on intracellular distribution of estrogen receptors. Life Sci. 1979 Sep 11;25(11):975-83. [41991 ]
- Bulger WH, Kupfer D: Effect of xenobiotic estrogens and structurally related compounds on 2-hydroxylation of estradiol and on other monooxygenase activities in rat liver. Biochem Pharmacol. 1983 Mar 15;32(6):1005-10. [6838646 ]
- Aguilar A, Borrell A: Reproductive transfer and variation of body load of organochlorine pollutants with age in fin whales (Balaenoptera physalus). Arch Environ Contam Toxicol. 1994 Nov;27(4):546-54. [7811111 ]
- Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
- ATSDR - Agency for Toxic Substances and Disease Registry (2007). Toxicological profile for 1,1,1-trichloroethane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- Wikipedia. 1,1,1-Trichloroethane. Last Updated 26 July 2009. [Link]
- International Programme on Chemical Safety (IPCS) INCHEM (2007). Poison Information Monograph for 1,1,1-Trichloroetahne. [Link]
- IARC (1979). Monograph of 1,1,1-Trichloroethane. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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