Dieldrin

Dieldrin
Names
IUPAC name
(1aR,2R,2aS,3S,6R,6aR,7S,7aS)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxirene
Other names
Dieldrin, HEOD
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.440 Edit this at Wikidata
KEGG
UNII
  • InChI=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- checkY
    Key: DFBKLUNHFCTMDC-PICURKEMSA-N checkY
  • InChI=1/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-
    Key: DFBKLUNHFCTMDC-PICURKEMBL
  • ClC5(Cl)[C@]3(Cl)C(\Cl)=C(\Cl)[C@@]5(Cl)[C@H]4[C@H]1C[C@H]([C@@H]2O[C@H]12)[C@@H]34
Properties
C12H8Cl6O
Molar mass 380.91 g/mol
Appearance colorless to light tan crystals
Density 1.75 g/cm3
Melting point 176 to 177 °C (349 to 351 °F; 449 to 450 K)
Boiling point 385 °C (725 °F; 658 K)
0.02%[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 moderately toxic and a suspected carcinogen[1]
Flash point noncombustible[1]
Lethal dose or concentration (LD, LC):
45 mg/kg (oral, rabbit)
49 mg/kg (oral, guinea pig)
38 mg/kg (oral, mouse)
65 mg/kg (oral, dog)
38 mg/kg (oral, rat)[2]
80 mg/m3 (cat, 4 hr)
13 mg/m3 (rat, 4 hr)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.25 mg/m3 [skin][1]
REL (Recommended)
 Ca TWA 0.25 mg/m3 [skin][1]
IDLH (Immediate danger)
 Ca [50 mg/m3][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Dieldrin is an organochlorine compound 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.

Originally developed in the 1940s as an alternative to DDT, dieldrin proved to be a highly effective insecticide and was very widely used during the 1950s to early 1970s. Endrin is a stereoisomer of dieldrin.

However, it is an extremely persistent organic pollutant; it does not easily break down. Furthermore, it tends to biomagnify as it is passed along the food chain.[3] Long-term exposure has proven toxic to a very wide range of animals including humans, far greater than to the original insect targets. People who on purpose or accidentally ate large amounts of aldrin or dieldrin have suffered convulsions (spasms), and some died. Workers who were exposed to lower amounts of these chemicals, but for a longer period of time, had headaches, dizziness, irritability, vomiting, and uncontrolled muscle movement.[4] For this reason, it is now banned in most of the world.

It has been linked to health problems such as Parkinson's disease, breast cancer, and immune, reproductive, and nervous system damage. It is also an endocrine disruptor, acting as an estrogen and antiandrogen, and can adversely affect testicle development in the fetus.[5]

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0206". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Dieldrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Cite error: The named reference Jorgensen2001 was invoked but never defined (see the help page).
  4. ^ "Aldrin/Dieldrin | ToxFAQs™ | ATSDR". wwwn.cdc.gov. Retrieved 2023-03-02.
  5. ^ Andersen HR, Vinggaard AM, Rasmussen TH, Gjermandsen IM, Bonefeld-Jørgensen EC (February 2002). "Effects of currently used pesticides in assays for estrogenicity, androgenicity, and aromatase activity in vitro". Toxicology and Applied Pharmacology. 179 (1): 1–12. Bibcode:2002ToxAP.179....1R. doi:10.1006/taap.2001.9347. PMID 11884232.