Aldrin (CHEM000021)

Record Information
Version1.0
Creation Date2009-03-06 18:57:56 UTC
Update Date2026-04-06 04:05:18 UTC
Accession NumberCHEM000021
Identification
Common NameAldrin
ClassSmall Molecule
Description
Aldrin is a chlorinated hydrocarbon used as an insecticide. Once in the insect, aldrin is oxidized into dieldrin, a neurotoxin. Due to the toxicity and ability of bioaccumulate of dieldrin, the use of aldrin is now banned in most parts of the world. (4)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ether
  • Human Neurotoxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC12H8Cl6
Average Molecular Mass364.910 g/mol
Monoisotopic Mass361.876 g/mol
CAS Registry Number309-00-2
IUPAC Name(1R,8S)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.1³,⁶.0²,⁷]dodeca-4,9-diene
Traditional Name(1R,8S)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.1³,⁶.0²,⁷]dodeca-4,9-diene
SMILESClC1=C(Cl)[C@]2(Cl)C3C4CC(C=C4)C3[C@@]1(Cl)C2(Cl)Cl
InChI IdentifierInChI=1S/C12H8Cl6/c13-8-9(14)11(16)7-5-2-1-4(3-5)6(7)10(8,15)12(11,17)18/h1-2,4-7H,3H2/t4?,5?,6?,7?,10-,11+
InChI KeyQBYJBZPUGVGKQQ-LYSYVJQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassVinyl halides
Sub ClassVinyl chlorides
Direct ParentVinyl chlorides
Alternative Parents
Substituents
  • Chloroalkene
  • Haloalkene
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • 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 Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point104°C
Boiling PointNot Available
Solubility1.7e-05 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility8.1e-05 g/LALOGPS
logP5.9ALOGPS
logP4.73ChemAxon
logS-6.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.76 m³·mol⁻¹ChemAxon
Polarizability30.85 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
Mechanism of ToxicityAldrin 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. Aldrin 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. (6, 1)
MetabolismAldrin is absorbed throught the gastrointestinal tract, lungs and skin. Following absorption, aldrin is redistributed primarily to fat via the lymphatic system. Once in the body, aldrin is readily converted to dieldrin, primarily in the liver by mixed-function oxidases of the cytochrome P-450 system, and to a lesser extent in the lung and skin. Aldrin may also be epoxidized to dieldrin by a prostaglandin synthetase-mediated pathway inextrahepatic tissues. 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. (1)
Toxicity ValuesLD50: 39 mg/kg (Oral, Rat) (8) LD50: 98 mg/kg (Dermal, Rat) (8) LD50: 150 mg/kg (Intraperitoneal, Rat) (7) LD50: 21 mg/kg (Intravenous, Mouse) (7)
Lethal Dose5 to 7 grams for an adult human. (9)
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (3)
Uses/SourcesAldrin is used as an insecticide. (4)
Minimum Risk LevelAcute Oral: 0.002 mg/kg/day (2) Chronic Oral: 0.00003 mg/kg/day (2)
Health EffectsAldrin is a neurotoxin and works by overstimulating the central nervous system. Ingestion of large amounts of aldrin causes convulsions and death. However, chronic exposure to lower amounts of aldrin also has adverse affects because it is oxidized to dieldrin, which accumulates in the body. Dieldrin is known to damage the nervous system, liver, and immune system. (1)
SymptomsExposure to aldrin results in headaches, dizziness, irritability, nausea and vomiting, cardiac arrhythmias, muscular weakness, uncontrolled muscle movements, hyperexcitability, seizures and coma. (1)
TreatmentTreatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (5)
Concentrations
Not Available
External Links
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 LinkAldrin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References