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Name Description
id 85
T3DB ID T3D0097
Name 1,1,1-Trichloroethane
Class SmallMolecule
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.
Categories "Household Toxin", "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Food Toxin", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Solvent", "Pollutant", "Food Toxin", "Metabolite", "Household Toxin", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "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"
CAS Number 71-55-6
Chemical Formula C2H3Cl3
Average Molecular Mass 133.40
Monoisotopic Mass 131.93
IUPAC Name 1,1,1-trichloroethane
Traditional Name trichloroethane
SMILES CC(Cl)(Cl)Cl
InChI Identifier InChI=1S/C2H3Cl3/c1-2(3,4)5/h1H3
InChI Key InChIKey=UOCLXMDMGBRAIB-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Organohalogen Compounds
Class Organochlorides
Sub Class
Direct Parent Organochlorides
Alternate Parents "Alkyl Chlorides"
Geometric Description Aliphatic Acyclic Compounds
Substituents "organochloride", "alkyl chloride", "Aliphatic Acyclic Compound", "Alkyl Halide"
Descriptors "a small molecule (MetaCyc)", "chloroethanes (ChEBI)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Liquid
Appearance Colorless liquid.
Melting Point -30.4°C
Boiling Point 74 °C (347°K, 165 °F)
Solubility 1.29 mg/mL at 25°C
LogP 2.49
Route of Exposure Oral (L306); inhalation (L306) ; dermal (L306)
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.
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. (L304)
Toxicity LD50: 11 240 mg/kg (Oral, Mouse) (L304) LD50: 9470 mg/kg (Oral, Guinea pig) (L304) LD50: 5660 mg/kg (Oral, Rabbit) (L304)
Lethal Dose
Carcinogenicity 3, not classifiable as to its carcinogenicity to humans. (L310)
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. (L304)
Minimum Risk Level Acute Inhalation: 2 ppm (L304) Intermediate Inhalation: 0.7 ppm (Gerbil) (L304) Intermediate Oral: 20 mg/kg/day (Mouse) (L304)
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.
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. (L306)
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.
DrugBank ID
HMDB ID HMDB41791
PubChem Compound ID 6278
ChEMBL ID CHEMBL16080
ChemSpider ID 6042
KEGG Compound ID C18246
UniProt ID 0
OMIM ID 0
ChEBI ID 36015
BioCyc ID CPD-8985
CTD ID
Stitch ID 1,1,1-Trichloroethane
PDB ID
ACToR ID 1413
Wikipedia Link http://en.wikipedia.org/wiki/1,1,1-trichloroethane
Creation Date 2009-03-06 18:58:04
Update Date 2014-12-24 20:21:06