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Record Information
Version1.0
Creation Date2009-03-06 18:58:01 UTC
Update Date2016-11-09 01:08:09 UTC
Accession NumberCHEM000065
Identification
Common NameEndrin aldehyde
ClassSmall Molecule
DescriptionEndrin aldehyde is a chemical produced by the breakdown of endrin. Endrin is a chlorinated hydrocarbon used as an insecticide on cotton, maize, and rice. It also acts as an avicide and rodenticide. Due to its toxicity and tendency to bioaccumulate, its use is now banned in most parts of the world. (2)
Contaminant Sources
  • Clean Air Act Chemicals
  • My Exposome Chemicals
  • T3DB toxins
Contaminant Type
  • Aldehyde
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC12H8Cl6O
Average Molecular Mass380.909 g/mol
Monoisotopic Mass377.871 g/mol
CAS Registry Number7421-93-4
IUPAC Name3,4,5,6,6,7-hexachloropentacyclo[6.3.0.0²,⁴.0³,⁷.0⁵,⁹]undecane-10-carbaldehyde
Traditional Name3,4,5,6,6,7-hexachloropentacyclo[6.3.0.0²,⁴.0³,⁷.0⁵,⁹]undecane-10-carbaldehyde
SMILESClC12C3C4CC(C=O)C5C4C(Cl)(C13Cl)C(Cl)(Cl)C25Cl
InChI IdentifierInChI=1S/C12H8Cl6O/c13-8-5-3(2-19)1-4-6(5)9(14,12(8,17)18)11(16)7(4)10(8,11)15/h2-7H,1H2
InChI KeyHCTWZIFNBBCVGM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMonoterpenoids
Alternative Parents
Substituents
  • Norbornane monoterpenoid
  • Monoterpenoid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Aldehyde
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility2.4e-05 mg/mL [SHIU,WY et al. (1990)]
Predicted Properties
PropertyValueSource
Water Solubility0.00052 g/LALOGPS
logP5.13ALOGPS
logP3.64ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)13.81ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.57 m³·mol⁻¹ChemAxon
Polarizability31.42 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-e9a909f2d1143fd4df7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-8e54cdc2778face09301View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03l1-1009000000-3826b8c09a41090be4ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-dd0b878b0faea7de29faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-0009000000-aca41db3422ff62ec805View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k96-8009000000-1723ef915419c134b138View in MoNA
MSMass Spectrum (Electron Ionization)splash10-014j-9883000000-5d1216a5ea4ff8d48974View in MoNA
Toxicity Profile
Route of ExposureOral (2)
Mechanism of ToxicityEndrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. Endrin also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. Endrin also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (1, 3)
MetabolismEndrin is absorbed orally and distributed primarily to the fat and skin. The major biotransformation product is anti-l 2-hydroxyendrin and the corresponding sulfate, as well as glucuronide metabolites. Anti- and syn-12-hydroxyendrin and 12-ketoendrin are the main toxic metabolites of endrin. Endrin and its metabolites are excreted in urine and feces. (3)
Toxicity ValuesLD50: >500 mg/kg (Oral, Mouse) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesEndrin is used as a pesticide. (2)
Minimum Risk LevelNot Available
Health EffectsEndrin poisoning affects primarily the nerve system. Exposure causes various harmful effects including hyperexcitability, severe central nervous system damage, and death. Endrin is also believed to cause birth defects. (1, 3)
SymptomsSymptoms that may result from endrin poisoning are headaches, dizziness, nervousness, confusion, nausea, vomiting, and convulsions. (3)
TreatmentTreatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (4)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID522524
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available