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Record Information
Version2.0
Creation Date2009-03-06 18:58:14 UTC
Update Date2014-12-24 20:21:17 UTC
Accession NumberT3D0183
Identification
Common NameChloroethane
ClassSmall Molecule
DescriptionChloroethane, also called ethyl chloride, is a colorless gas at room temperature and pressure, with a characteristically sharp odor. People can smell chloroethane in the air at levels above 4 parts chloroethane in a million parts of air by volume (ppm). It can be smelled in water at levels above 0.02 parts chloroethane in a million parts of water (ppm). In pressurized containers, chloroethane exists as a liquid. However, the liquid evaporates quickly when exposed to air. It catches fire easily and is very dangerous when exposed to heat or flame. Chloroethane does not occur naturally in the environment. It is present in the environment as a result of human activity. In the past, the largest single use for chloroethane was for the production of tetraethyl lead, which is a gasoline additive. However, production of chloroethane has decreased dramatically as a result of stricter government regulations controlling lead in gasoline. Other applications include use in the production of ethyl cellulose, dyes, medicinal drugs, and other commercial chemicals, and use as a solvent and refrigerant. It is used to numb skin prior to medical procedures such as ear piercing and skin biopsies, and it is used in the treatment of sports injuries. (4)
Compound Type
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1-Chloroethane
Anodynon
Chelen
Chlorene
Chlorethyl
Chloryl
Chloryl anesthetic
EtCl
Ether hydrochloric
Ether muriatic
Ethyl chloride
Hydrochloric ether
Kelene
Mono-chloroethane
Monochlorethane
Monochloroethane
Muriatic ether
Narcotile
Chemical FormulaC2H5Cl
Average Molecular Mass64.514 g/mol
Monoisotopic Mass64.008 g/mol
CAS Registry Number75-00-3
IUPAC Namechloroethane
Traditional Nameethyl chloride
SMILESCCCl
InChI IdentifierInChI=1S/C2H5Cl/c1-2-3/h2H2,1H3
InChI KeyInChIKey=HRYZWHHZPQKTII-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
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateGas
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-138.7°C
Boiling PointNot Available
Solubility6.71 mg/mL at 25 °C [HORVATH,AL et al. (1999)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.1 g/LALOGPS
logP1.47ALOGPS
logP1.19ChemAxon
logS-0.66ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.06 m³·mol⁻¹ChemAxon
Polarizability6.42 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-189a942366091e0718c5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-4ebb55acce146f8b18b7JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-344429f368435644d523JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-ff8ba6a1cf5cd85d51e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-9000000000-8f9064b7e272fb20eda5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-351a762c6fc3dee4c33cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-2c33af82cafddccc3d56JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-97065b07abf1a3f8c6edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-34ef963de96f69d59b37JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-ccbcadecc1a8a92cafbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-9000000000-2bf56a2252ff6edcbcf8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-23a70a049fbaf7901cd4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-c2fa753da65a4bac80a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-c2fa753da65a4bac80a1JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-11f0eb48855aebd37893JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureInhalation (4) ; dermal (4) ; eye contact (4) ; oral (4)
Mechanism of ToxicityChloroethane targets the central nervous system and the heart. The lipophilicity of chloroethane suggests it acts upon the lipid layer of cellular membrane or the hydrophobic areas of specific membrane-bound cellular proteins. Euphoria and excitement resulting from the effects of chloroethane on the central nervous system induice catecholamine release. At levels adequate to induce anesthesia, chloroethane sensitizes the heart to the effects of catecholamines. This sensitization, along with asphyxia and hypoxia, can cause arrhythmias, and death. (4)
MetabolismBecause chloroethane is a small lipophilic compound, simple diffusion accounts for its absorption across membranes, and its higher affinity for lipids determines its distribution. Metabolism of chloroethane is believed to occur exclusively in the liver. The two major pathways are the production of acetaldehyde by cytochrome P450, and conjugation of chloroethane with glutathione to form S-ethyl-glutathione (catalyzed by glutathione S-transferase). The P450 enzyme CYP2El is responsible for chloroethane metabolism. The latter reaction is catalyzed by glutathione-S-transferase enzymes. Acetaldehyde is rapidly metabolized to acetic acid by aldehyde dehydrogenase. S-ethyl-glutathione can be furhter metabolized to S-ethyl-N-acety-L-cysteine (by γ-glutamyltranspeptidase, cysteinyl glycinase, and N-acetyltransferase, NAT) or S-ethyl-L-cysteine (by γ-glutamyltranspeptidase and cysteinyl glycinase). Chloroethane is eliminated from the body by pulmonary exhalation. (4)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (3)
Uses/SourcesIn the past, the largest single use for chloroethane was for the production of tetraethyl lead, which is a gasoline additive. However, production of chloroethane has decreased dramatically as a result of stricter government regulations controlling lead in gasoline. Other applications include use in the production of ethyl cellulose, dyes, medicinal drugs, and other commercial chemicals, and use as a solvent and refrigerant. It is used to numb skin prior to medical procedures such as ear piercing and skin biopsies, and it is used in the treatment of sports injuries. Exposure may result from breathing air containing chloroethane vapor, drinking water containing chloroethane, and through skin or eye contact. (4)
Minimum Risk LevelAcute Inhalation: 15 ppm (Mouse) (4)
Health EffectsChloroethane poisoning may cause liver and kidney damage. Decreased defensive responses against illness, neurological effects following inhalation, effects on the nervous system, and cardiac depression can result from the exposure to this toxin. Moreover, respiratory paralysis and toxic injury to the heart have been reported following anesthesia with chloroethane. (4)
SymptomsSeveral sypmtoms can be manifested after inhalation of chloroethane, such as Jerking eye movements, an inability to control muscles in voluntary movements, difficulty in speaking clearly, an inability to perform finger tapping exercises, sluggish lower limb reflexes, seizures, difficulties in walking, disorientation, short-term memory loss, and hallucinations affecting sight and hearing. Moreover, dizziness, headache, feelings of drunkenness, nausea, vomiting, and abdominal cramps can occur. Redness, pain, and blurred vision can result from eye exposure. Long time skin exposure to chloroethane can cause frostbite. (4, 5)
TreatmentIf the exposure occurred through inhalation, 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 seizures, administer a benzodiazepine IV, diazepam or lorazepam; consider phenobarbital or propofol if seizures recur after diazepam. Monitor for hypotension, dysrhythmias, respiratory depression, and need for endotracheal intubation. Evaluate for hypoglycemia, electrolyte disturbances, hypoxia. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes if the exposure occurred through eye contact. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy; patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6337
ChEMBL IDCHEMBL46058
ChemSpider ID6097
KEGG IDC18248
UniProt IDNot Available
OMIM ID
ChEBI ID47554
BioCyc IDCPD-4521
CTD IDD005018
Stitch IDChloroethane
PDB IDNot Available
ACToR ID304
Wikipedia LinkEthyl chloride
References
Synthesis ReferenceNot Available
MSDST3D0183.pdf
General References
  1. Gargas ML, Sweeney LM, Himmelstein MW, Pottenger LH, Bus JS, Holder JW: Physiologically based pharmacokinetic modeling of chloroethane disposition in mice, rats, and women. Toxicol Sci. 2008 Jul;104(1):54-66. doi: 10.1093/toxsci/kfn064. Epub 2008 Apr 2. [18385209 ]
  2. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  3. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  4. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for chloroethane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  5. International Programme on Chemical Safety (IPCS) INCHEM (2000). Poison Information Monograph for Chloroethane. [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.