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Record Information
Version2.0
Creation Date2009-03-06 18:58:12 UTC
Update Date2014-12-24 20:21:15 UTC
Accession NumberT3D0163
Identification
Common Name1,1,2-Trichloroethane
ClassSmall Molecule
Description1,1,2-Trichloroethane is a colorless, sweet-smelling liquid that does not burn easily and boils at a higher temperature than water. It is used mostly where 1,1-dichloroethene (vinylidene chloride) is made. 1,1,2-Trichloroethane is used as a solvent. When it is released into the environment, most 1,1,2-trichloroethane finally ends up in the air, but some may enter groundwater. Breakdown in both the air and groundwater is slow. (5)
Compound Type
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1,1, 2-Trichloroethane
1,1,2-Trichloraethan
1,1,2-Trichlorethane
1,2,2-Trichloroethane
beta-T
Beta-trichloroethane
Beta.-trichloroethane
Ethane trichloride
Trichloroethane
Vinyl trichloride
Vinyltrichloride
Chemical FormulaC2H3Cl3
Average Molecular Mass133.404 g/mol
Monoisotopic Mass131.930 g/mol
CAS Registry Number79-00-5
IUPAC Name1,1,2-trichloroethane
Traditional Name1,1, 2-trichloroethane
SMILESClCC(Cl)Cl
InChI IdentifierInChI=1S/C2H3Cl3/c3-1-2(4)5/h2H,1H2
InChI KeyInChIKey=UBOXGVDOUJQMTN-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganochlorides
Sub ClassNot Available
Direct ParentOrganochlorides
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-36.6°C
Boiling Point110 - 115 °C
Solubility4.59 mg/mL at 25 °C [HORVATH,AL et al. (1999)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.93 g/LALOGPS
logP2.02ALOGPS
logP2.17ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.71 m³·mol⁻¹ChemAxon
Polarizability10.43 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9100000000-bf79232c76a22826ba5cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1900000000-3f6b6c4778619860fc19JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-de14959b0cb16e8cd707JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-9000000000-eece4c8a26c8a21d5fb7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-cc11fb3585800aaf8723JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9400000000-bcf58e3a5f886b9be8cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-9058e4afd6f1129806b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-6838b4c597e6d80ac4e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-c2fa753da65a4bac80a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-7900000000-ff817bfd636e4a77346cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-c8f6da92e011fc99d023JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-c8f6da92e011fc99d023JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-9000000000-97d9dd18a5aad6cec972JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-316c9aca46098f901713JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureInhalation (6) ; oral (6) ; dermal (6)
Mechanism of ToxicityAcyl chlorides and free radicals formed during the metabolism of 1,1,2-trichloroethane are reactive metabolites that can bind to proteins and nucleic acids (DNA, RNA), and are suspected of being cytotoxic, mutagenic, and carginogenic. (5, 1)
MetabolismAfter 1,1,2-trichloroethane enters the body, it is carried by the blood to organs and tissues such as the liver, kidney, brain, heart, spleen, and fat. The primary metabolites identified are chloroacetic acid, S-carboxymethylcysteine, and thiodiacetic acid. S-carboxymethycysteine and thiodiacetic acid are formed from 1,1,2-trichloroethane following conjugation with glutathione. Chloroacetic acid is formed by hepatic cytochrome P-450. This reaction is thought to proceed via the acyl chloride. Cytochrome P-450 can also produce free radicals from 1,1,2-trichloroethane. Experiments show that most 1,1,2-trichloroethane leaves the body unchanged in the breath and as other substances that it is changed into in the urine in about 1 day. (5)
Toxicity ValuesLD50: 837 mg/kg (Oral, Rat) (7) LD50: 5.38 g/kg (Dermal, Rabbit) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (4)
Uses/Sources1,1,2-Trichloroethane is used as a solvent. Exposure to 1,1,2-trichloroethane would most likely be from breathing vapors of the chemical or from skin contact. Drinking contaminated water is also a route of exposure. (5)
Minimum Risk LevelAcute Oral: 0.3 mg/kg/day (Mouse) (5) Intermediate Oral: 0.04 mg/kg/day (Mouse) 9L422)
Health EffectsInhalation of high levels of 1,1,2-trichloroethanein can affect the nervous system and cause sleepiness. 1,1,2-Trichloroethane may also affect the liver, kidney, and digestive tract, produce skin irritation, and affect the body's ability to fight infections. (5)
SymptomsInhalation or ingestion of 1,1,2-trichloroethane can cause dizziness, drowsiness, headache, nausea, shortness of breath, and unconsciousness. The compound can be absorbed following dermal contact. Skin exposure can also lead to temporary stinging and burning pain. Other symptoms of exposure to this compound may include irritation of the skin, eyes, nose, mucous membranes, and upper respiratory tract. (6, 2)
TreatmentFollowing ingestion, administer charcoal as a slurry (240 mL water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents, 25 to 50 g in children (1 to 12 years), and 1 g/kg in infants less than 1 year old. Consider gastric lavage after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion. In case of seizures, administer a benzodiazepine IV. Following inhalation exposure, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. (3)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6574
ChEMBL IDCHEMBL43882
ChemSpider ID6326
KEGG IDC19536
UniProt IDNot Available
OMIM ID
ChEBI ID36018
BioCyc IDCPD-8985
CTD IDC024567
Stitch ID1,1,2-Trichloroethane
PDB IDNot Available
ACToR ID1412
Wikipedia Link1,1,2-Trichloroethane
References
Synthesis ReferenceNot Available
MSDST3D0163.pdf
General References
  1. Mazzullo M, Colacci A, Grilli S, Prodi G, Arfellini G: 1,1,2-Trichloroethane: evidence of genotoxicity from short-term tests. Jpn J Cancer Res. 1986 Jun;77(6):532-9. [2426232 ]
  2. Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  3. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (1989). Toxicological profile for 1,1,2-trichloroethane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  6. International Programme on Chemical Safety (IPCS) INCHEM (1995). Poison Information Monograph for Cadmium. [Link]
  7. Organization for Economic Cooperation and Development (2000). Screening Information Data Set for 1,1,2-Trichloroethane (79-00-5). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

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.
3. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1989). Toxicological profile for 1,1,2-trichloroethane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
4. RNA
References
  1. Mazzullo M, Colacci A, Grilli S, Prodi G, Arfellini G: 1,1,2-Trichloroethane: evidence of genotoxicity from short-term tests. Jpn J Cancer Res. 1986 Jun;77(6):532-9. [2426232 ]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]