Dieldrin (CHEM000015)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (46)XML
Record Information
Version1.0
Creation Date2009-03-06 18:57:55 UTC
Update Date2026-04-15 17:36:28 UTC
Accession NumberCHEM000015
Identification
Common NameDieldrin
ClassSmall Molecule
DescriptionDieldrin is a chlorinated hydrocarbon used as an insecticide, either by itself or as a component of the closely related insectide aldrin. As dieldrin is neurotoxin and tends to bioaccumulate, its use is now banned in most parts of the world. (3) Dieldrin is a chlorinated hydrocarbon originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. Dieldrin is closely related to aldrin, which reacts further to form dieldrin. Aldrin is not toxic to insects; it is oxidized in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels-Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ether
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1Aalpha,2beta,2aalpha,3beta,6beta,6aalpha,7beta,7aalpha)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxireneChEBI
(1R,4S,4AS,5R,6R,7S,8S,8ar)-1,2,3,4,10,10-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthaleneChEBI
1,2,3,4,10,10-Hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-endo-exo-5,8-dimethanonaphthaleneChEBI
HEODChEBI
(1Aalpha,2b,2aalpha,3b,6b,6aalpha,7b,7aalpha)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxireneGenerator
(1Aalpha,2β,2aalpha,3β,6β,6aalpha,7β,7aalpha)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxireneGenerator
Alvit-55MeSH
Alvit 55MeSH
Alvit55MeSH
Chemical FormulaC12H8Cl6O
Average Molecular Mass380.909 g/mol
Monoisotopic Mass377.871 g/mol
CAS Registry Number60-57-1
IUPAC Name(1R,2S,3S,6R,7R,8S,9S,11R)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.1³,⁶.0²,⁷.0⁹,¹¹]tridec-4-ene
Traditional Namedieldrin
SMILES[H][C@]12O[C@@]1([H])[C@@]1([H])C[C@]2([H])[C@@]2([H])[C@]1([H])[C@@]1(Cl)C(Cl)=C(Cl)[C@]2(Cl)C1(Cl)Cl
InChI IdentifierInChI=1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4+,5-,6-,7+,10+,11-
InChI KeyDFBKLUNHFCTMDC-PICURKEMSA-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
  • Monoterpenoid
  • Norbornane monoterpenoid
  • Oxepane
  • Oxane
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Vinyl chloride
  • Vinyl halide
  • Organoheterocyclic compound
  • Haloalkene
  • Chloroalkene
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alkyl chloride
  • Alkyl halide
  • Organic oxygen compound
  • Organohalogen compound
  • Organochloride
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell junction
  • Cytosol
  • Endoplasmic reticulum
  • Extracellular
  • Lysosome
  • Membrane
  • Microsome
  • Mitochondrion
  • Nucleolus
  • Peroxisome
  • Plasma Membrane
  • Sarcoplasmic Reticulum
  • Synaptic Vesicle
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Base excision repairNot Availablemap03410
ProteasomeNot AvailableNot Available
Phenylalanine metabolismNot Availablemap00360
Oxidative phosphorylationNot Availablemap00190
Circadian rhythmNot Availablemap04710
Insulin secretionNot Availablemap04911
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point175.5°C
Boiling PointNot Available
Solubility0.000195 mg/mL at 25 °C [BIGGAR,JW & RIGGS,RI (1974)]
Predicted Properties
PropertyValueSource
Water Solubility0.0002 g/LALOGPS
logP4.98ALOGPS
logP3.95ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.01 m³·mol⁻¹ChemAxon
Polarizability31.36 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-4e3ab80ba2cb5f78445dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0009000000-47b57ee68ea2b95cb4a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-9124000000-f5c8679adbd456c1b9e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-c15682ff19a328a64b01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-41a18726a0ad03aeb1f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2209000000-4c9e51dcaa850bbc46a8Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityDieldrin 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. Dieldrin 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 CNS. This results in hyperexcitation and generalized seizures. Dieldrin also binds to alpha-synuclein, leading to the formation of intracellular fibrils. (9, 4)
MetabolismDieldrin is absorbed throught the gastrointestinal tract, lungs and skin. Following absorption, dieldrin is redistributed primarily to fat via the lymphatic system. Dieldrin is metabolized by liver microsomal monooxygenases and epoxide hydratases. Its metabolites, of which the primary one is 9-hydroxydieldrin, are excreted in the faeces. (4)
Toxicity ValuesLD50: 38 mg/kg (Oral, Rat) (10) LD50: 56 mg/kg (Dermal, Rat) (10) LD50: 49 mg/kg (Subcutaneous, Rat) (7) LD50: 9 mg/kg (Intravenous, Rat) (10) LC50: 13 mg/m3 over 4 hours (Inhalation, Rat) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (6)
Uses/SourcesDieldrin is used as an insecticide. (4)
Minimum Risk LevelIntermediate Oral: 0.0001 mg/kg/day (5) Chronic Oral: 0.00005 mg/kg/day (5)
Health EffectsDieldrin is a neurotoxin and works by overstimulating the central nervous system. Ingestion of large amounts of dieldrin causes convulsions and death. However, chronic exposure to lower amounts of dieldrin also has adverse effects because dieldrin accumulates in the body. Dieldrin is known to damage the nervous system, liver, and immune system. (4)
SymptomsExposure to dieldrin results in headaches, dizziness, irritability, nausea and vomiting, cardiac arrhythmias, muscular weakness, uncontrolled muscle movements, hyperexcitability, seizures and coma. (4)
TreatmentTreatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (8)
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 LinkDieldrin
Chemspider IDNot Available
ChEBI ID34696
PubChem Compound IDNot Available
Kegg Compound IDC13718
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17848404
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17999924
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18497062
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20602524
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21724225
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22281775
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23001942
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23726008
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23763672
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=8597127