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Showing metabocard for 1,1,1-Trichloroethane (HMDB0041791)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:39:39 UTC
Update Date2021-10-13 08:36:49 UTC
HMDB IDHMDB0041791
Secondary Accession Numbers
  • HMDB41791
Metabolite Identification
Common Name1,1,1-Trichloroethane
Description1,1,1-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.
Structure
Data?1563863703
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041791 (1,1,1-Trichloroethane)


  Mrv1652305261923512D          

  5  4  0  0  0  0            999 V2000
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  2  1  0  0  0  0
M  END
Download

3D MOL for HMDB0041791 (1,1,1-Trichloroethane)

HMDB0041791
     RDKit          3D
1,1,1-Trichloroethane
  8  7  0  0  0  0  0  0  0  0999 V2000
   -0.8394    0.0491   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -0.0471    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413    1.4312   -0.5516 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -0.2405    1.8124 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3383   -1.4053   -0.8536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3988   -0.0519    0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    1.0388   -0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1898   -0.7742   -0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
M  END
Download

3D SDF for HMDB0041791 (1,1,1-Trichloroethane)


  Mrv1652305261923512D          

  5  4  0  0  0  0            999 V2000
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  2  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041791

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(Cl)(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C2H3Cl3/c1-2(3,4)5/h1H3

> <INCHI_KEY>
UOCLXMDMGBRAIB-UHFFFAOYSA-N

> <FORMULA>
C2H3Cl3

> <MOLECULAR_WEIGHT>
133.404

> <EXACT_MASS>
131.930033217

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
10.354037673293911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,1,1-trichloroethane

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.075951796

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
26.2173

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trichloroethane

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0041791 (1,1,1-Trichloroethane)

HMDB0041791
     RDKit          3D
1,1,1-Trichloroethane
  8  7  0  0  0  0  0  0  0  0999 V2000
   -0.8394    0.0491   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -0.0471    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413    1.4312   -0.5516 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -0.2405    1.8124 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3383   -1.4053   -0.8536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3988   -0.0519    0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    1.0388   -0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1898   -0.7742   -0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
M  END
Download

PDB for HMDB0041791 (1,1,1-Trichloroethane)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0       1.540   1.540   0.000  0.00  0.00          Cl+0
HETATM    4 Cl   UNK     0       3.080   0.000   0.000  0.00  0.00          Cl+0
HETATM    5 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
Download

3D PDB for HMDB0041791 (1,1,1-Trichloroethane)

COMPND    HMDB0041791
HETATM    1  C1  UNL     1      -0.839   0.049  -0.079  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.653  -0.047   0.090  1.00  0.00           C  
HETATM    3 CL1  UNL     1       1.441   1.431  -0.552  1.00  0.00          CL  
HETATM    4 CL2  UNL     1       1.088  -0.240   1.812  1.00  0.00          CL  
HETATM    5 CL3  UNL     1       1.338  -1.405  -0.854  1.00  0.00          CL  
HETATM    6  H1  UNL     1      -1.399  -0.052   0.870  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.092   1.039  -0.536  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.190  -0.774  -0.752  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4    5
END
Download

SMILES for HMDB0041791 (1,1,1-Trichloroethane)

CC(Cl)(Cl)Cl
Download

INCHI for HMDB0041791 (1,1,1-Trichloroethane)

InChI=1S/C2H3Cl3/c1-2(3,4)5/h1H3
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,1,1-TCEChEBI
1,1,1-TrichloraethanChEBI
1,1,1-TrichlorethaneChEBI
alpha-TChEBI
alpha-TrichloroethaneChEBI
MethylchloroformChEBI
MethyltrichloromethaneChEBI
Trichloro-1,1,1-ethaneChEBI
a-TGenerator
α-TGenerator
a-TrichloroethaneGenerator
Α-trichloroethaneGenerator
1,1,1 TrichloroethaneHMDB
1,1,1-TrichlorathanHMDB
1,1,1-Trichloro-2-(O-chlorophenyl)-2-(p-chlorophenyl)ethaneHMDB
1,1,1-Trichloro-ethaneHMDB
1,1,1-Trichloroethane (acd/name 4.0)HMDB
1,1,1-TricloroetanoHMDB
2-(2-Chlorophenyl)-2-(4-chlorophenyl)-1,1,1-trichloroethaneHMDB
Aerothene TTHMDB
CH3CCL3HMDB
ChloroteneHMDB
Chlorothane nuHMDB
ChlorotheneHMDB
Chlorothene nuHMDB
Chlorothene SMHMDB
Chlorothene VGHMDB
Chlorothene, inhibitedHMDB
ChlortenHMDB
CleaniteHMDB
Distillex DS1HMDB
EthanaHMDB
Ethana nuHMDB
Genklene LBHMDB
ICI-CF 2HMDB
InhibisolHMDB
Methyl-chloroformHMDB
Rcra waste number u226HMDB
Solvent 111HMDB
SolvethaneHMDB
TafcleanHMDB
Three one aHMDB
Three one SHMDB
Tri-ethaneHMDB
TrichloroethaneHMDB
TrichloromethylmethaneHMDB
Chemical FormulaC2H3Cl3
Average Molecular Weight133.404
Monoisotopic Molecular Weight131.930033217
IUPAC Name1,1,1-trichloroethane
Traditional Nametrichloroethane
CAS Registry Number71-55-6
SMILES
CC(Cl)(Cl)Cl
InChI Identifier
InChI=1S/C2H3Cl3/c1-2(3,4)5/h1H3
InChI KeyUOCLXMDMGBRAIB-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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-30.4 °CNot Available
Boiling Point74.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.29 mg/mL at 25 °CNot Available
LogP2.49Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.13 g/LALOGPS
logP10(2.45) g/LALOGPS
logP10(2.08) g/LChemAxon
logS10(-1.8) g/LALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.22 m³·mol⁻¹ChemAxon
Polarizability10.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,1,1-TrichloroethaneCC(Cl)(Cl)Cl909.5Standard polar33892256
1,1,1-TrichloroethaneCC(Cl)(Cl)Cl632.7Standard non polar33892256
1,1,1-TrichloroethaneCC(Cl)(Cl)Cl640.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1,1,1-Trichloroethane EI-B (Non-derivatized)splash10-0002-9000000000-acdd1de2f2f494cc9f332017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1,1-Trichloroethane EI-B (Non-derivatized)splash10-0002-9100000000-93c8b64bf9a3e2f74a6d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1,1-Trichloroethane CI-B (Non-derivatized)splash10-0002-9100000000-756b9bd2a76d828e0d452017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1,1-Trichloroethane EI-B (Non-derivatized)splash10-0002-9000000000-acdd1de2f2f494cc9f332018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1,1-Trichloroethane EI-B (Non-derivatized)splash10-0002-9100000000-93c8b64bf9a3e2f74a6d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1,1-Trichloroethane CI-B (Non-derivatized)splash10-0002-9100000000-756b9bd2a76d828e0d452018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,1,1-Trichloroethane GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9600000000-c081dcbb807720cca52e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,1,1-Trichloroethane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9100000000-09ba0e8b7b22dd7863382014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 10V, Positive-QTOFsplash10-001i-0900000000-e0c9bb24f0f03e2e03d62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 20V, Positive-QTOFsplash10-001i-0900000000-e0c9bb24f0f03e2e03d62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 40V, Positive-QTOFsplash10-001i-2900000000-86949d54288e0f2f7c232016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 10V, Negative-QTOFsplash10-001i-0900000000-069dedae972a3a56c2ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 20V, Negative-QTOFsplash10-001i-1900000000-6dca5faa37b128ac40a72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 40V, Negative-QTOFsplash10-0006-9100000000-53cbfa180588956738d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 10V, Positive-QTOFsplash10-001i-0900000000-c8f6da92e011fc99d0232021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 20V, Positive-QTOFsplash10-001i-0900000000-c8f6da92e011fc99d0232021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 40V, Positive-QTOFsplash10-0002-9000000000-764e8b6db288ec387c282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 10V, Negative-QTOFsplash10-001i-0900000000-6838b4c597e6d80ac4e22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 20V, Negative-QTOFsplash10-001i-0900000000-6838b4c597e6d80ac4e22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroethane 40V, Negative-QTOFsplash10-001i-0900000000-6838b4c597e6d80ac4e22021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6042
KEGG Compound IDC18246
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,1,1-Trichloroethane
METLIN IDNot Available
PubChem Compound6278
PDB IDNot Available
ChEBI ID36015
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1143221
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:6838646 ]
  2. 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. [PubMed:23102696 ]
  3. 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. [PubMed:12781216 ]
  4. 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. [PubMed:6499760 ]
  5. 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. [PubMed:8968093 ]
  6. 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. [PubMed:10580314 ]
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