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Chlordecone

HCID 299
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
143-50-0
Standard SMILES
O=C1C2(Cl)C3(Cl)C4(Cl)C(Cl)(Cl)C5(Cl)C3(Cl)C1(Cl)C5(Cl)C24Cl
InChIKey
LHHGDZSESBACKH-UHFFFAOYSA-N
Molecular formula
C10Cl10O
Average molar mass
490.6 g/mol
Monoisotopic mass
485.683442

Overview

Mirex and chlordecone are two separate, but chemically similar, manufactured insecticides that do not occur naturally in the environment. Mirex is a white crystalline solid, and chlordecone is a tan-white crystalline solid. Both chemicals are odorless. Mirex and chlordecone have not been manufactured or used in the United States since 1978. Mirex was used to control fire ants, and as a flame retardant in plastics, rubber, paint, paper, and electrical goods from 1959 to 1972. Chlordecone was used as an insecticide on tobacco, ornamental shrubs, bananas, and citrus trees, and in ant and roach traps. Mirex was sold as a flame retardant under the trade name Dechlorane, and chlordecone was also known as Kepone. Use of trade names is for identification only and does not imply endorsement by the Agency for Toxic Substances and Disease Registry, the Public Health Service, or the U.S. Department of Health and Human Services.

Names & identifiers

Preferred name
Chlordecone
IUPAC
1,2,3,4,6,7,8,9,10,10-decachloropentacyclo[5.3.0.02,6.03,9.04,8]decan-5-one
English name
Chlordecone
Molecular formula
C10Cl10O
Molecular weight
490.64

Names & synonyms

chlordeconeKepone143-50-0ClordeconeDecachloroketoneMerexCompound 1189General chemicals 1189Rcra waste number U142DecachlorotetracyclodecanoneDTXSID1020770GC 1189
Show more names
CHLORDECONo-4-oneent16,391ENT-16391KEPONE(R)hlordecane
NCI-C00191ENT 16,391NSC 124074RG5XJ88UDFGC-1189Decachlorotetrahydro-4,7-methanoindeneoneCHEBI:16548Decachloro-1,3,4-metheno-2H-cyclobuta(cd)pentalen-2-one

Database identifiers

CAS
143-50-0
PubChem CID
299
DTXSID
DTXSID1020770
ChEMBL
CHEMBL462576
ChEBI
CHEBI:16548
UNII
RG5XJ88UDF
EC Number
205-601-3
Nikkaji
J10.213J

Properties

Computed structural properties

XLogP
3.9
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
21
Formal charge
0
Complexity
631

Experimental & physicochemical properties

Chemical ClassesCarcinogens
Pesticides · 4 items

Pesticide -> EPA IRIS

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organochlorine Pesticides

LogP · 3 items

log Kow = 5.41

3.45

5.41

OdorOdorless
Density · 2 items

1.64 g/cu cm at 25 °C

1.61 @25 °C

Color/Form · 2 items

Crystals

Tan to white, crystalline solid

Solubility · 6 items

less than 1 mg/mL at 73 °F (NTP, 1992)

Solubility in water: 4000 mg/L at 100 °C

0.470 lb/100 lb water at 212 °F

In water, 2.70 mg/L at 25 °C

Soluble in strongly alkaline aqueous solution; readily soluble in acetone, less soluble in benzene & light petroleum

Slightly soluble in hydrocarbon solvents. Soluble in alcohols, ketones, acetic acid.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P203, P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P318, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P318, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 3 items

Hazard Traits - Bioaccumulation; Carcinogenicity; Developmental Toxicity; Environmental Persistence

Substance: Chlordecone

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1,3,4-Metheno-2H-cyclobuta[cd]pentalen-2-one, 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 2 items

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialThis chemical is a noncombustible solid.
Health HazardsINHALATION AND INGESTION: These symptoms present in all affected patients - Neurologic Impairment - anxiety, irritability, memory disturbance, headache, tremors, opsiclonus, stuttering, slurred speech, and abnormal tandem gait. (USCG, 1999)

Chemistry & industry

Pharmacology

Mechanism of Action · 4 items

Several studies have attempted to define the mechanism by which ... chlordecone inhibits hepatobiliary excretion. At very high levels, chlordecone depressed ATPase activity or cellular energy utilization at moderate to relatively high doses (2.5 to 100 mg/kg/day and 50 to 100 mg/kg/day, respectively) thereby inhibiting the biliary excretion of substances. The inhibition does not appear to be due to inhibition of the metabolism of the substance to be excreted in the bile or to decreased bile flow. Possible explanations for the decreased excretion of metabolites in the bile include decreased uptake of substances by the hepatocyte, a decreased transfer of chemicals from the hepatocyte to the bile, and leaking of metabolites from the bile duct via a paracellular pathway. The decrease in transfer may be due to decreased permeability of the canalicular membrane resulting from inhibition of the mg2+ATPase activity of the bile canaliculi or perturbations of plasma membrane.

At the cellular level, chlordecone causes spontaneous neurotransmitter release and increases in free intracellular calcium in synaptosomes. This appears to be due at least in part to increased permeability of the plasma membrane, activation of voltage-dependent calcium channels, and inhibition of brain mitochondrial calcium uptake. Chlordecone also decreased the activity of calmodulin-stimulated enzymes and of enzymes integral to maintenance of neuronal energy and ionic gradients; Na+K+ATPase, oligomycin-sensitive mg2+ATPase and Ca2+ATPase activities in brain tissues have been shown to be decreased by exposure to chlordecone both in vivo and in vitro.

Organochlorine (OC) pesticides constitute a major class of persistent and toxic organic pollutants, known to modulate drug-detoxifying enzymes. In the present study, OCs were demonstrated to also alter the activity and expression of human hepatic drug transporters. Activity of the sinusoidal influx transporter OCT1 (organic cation transporter 1) was thus inhibited by endosulfan, chlordane, heptachlor, lindane, and dieldrine, but not by dichlorodiphenyltrichloroethane isomers, whereas those of the canalicular efflux pumps MRP2 (multidrug resistance-associated protein 2) and BCRP (breast cancer resistance protein) were blocked by endosulfan, chlordane, heptachlor, and chlordecone; this latter OC additionally inhibited the multidrug resistance gene 1 (MDR1)/P-glycoprotein (P-gp) activity. OCs, except endosulfan, were next found to induce MDR1/P-gp and MRP2 mRNA expressions in hepatoma HepaRG cells; some of them also upregulated BCRP. By contrast, expression of sinusoidal transporters was not impaired (organic anion-transporting polypeptide (OATP) 1B1 and OATP2B1) or was downregulated (sodium taurocholate co-transporting polypeptide (NTCP) and OCT1). Such regulations of drug transporter activity and expression, depending on the respective nature of OCs and transporters, may contribute to the toxicity of OC pesticides.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Corrosivity
Noncorrosive
Flash Point>100.00 °C (>212.00 °F)
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 3 items

Sublimes with decomposition at 662.0 °F (USCG, 1999)

Sublimes

Sublimes

Decomposition · 2 items

Hazardous decomposition products formed under fire conditions - Carbon oxides, hydrogen chloride gas.

Decomposes at 350 °C.

Physicochemical properties

Melting point
350 ℃ · 350℃ (DEC.)
Boiling point
450.5 · 450.5±45.0 °C(Predicted)
Density
2.27 · 2.27
vapor pressure
2.25 x · 2.25 x 10-7 mmHg at 25 °C (Kilzer et al., 1979)
Flash point
100 °C · >100 °C
storage temp.
0 · 0-6°C
solubility
Soluble in acetic acid, alcohols, and ketones (Windholz et al., 1983)
form
Tan to white crystalline solid
Water Solubility
7.6 at · (mg/L):7.600 at 24 °C (shake flask-nephelometry, Hollifield, 1979) 2.7 at 20–25 °C (Kilzer et al., 1979)
Merck
13 · 13,2098
Henry's Law Constant
(x 10-2 atmm3/mol): 3.11 at 25 °C (approximate - calculated from experimentally determined water solubility and vapor pressure values)
Exposure limits
1 mg/m3 · NIOSH REL: TWA 1 mg/m3.
Toxicology and Carcinogenesis
Report on Carcinogenesis Bioassay of Technical Grade Chlordecone (Kepone) (CASRN 143-50-0)
EWG's Food Scores
8 · 8
FDA UNII
5 XJ88UDF · RG5XJ88UDF
Proposition 65 List
Chlordecone (Kepone)
IARC
2 B · 2B (Vol. 20, Sup 7) 1987
EPA Substance Registry System
Chlordecone (143-50-0)
Toxicological Profile|ATSDR
Chlordecone|Toxicological Profile|ATSDR
Symbol(GHS)
6 · GHS06,GHS08,GHS09
Signal word
Danger
Hazard statements
301 · H301-H311-H351-H410
Precautionary statements
264 · P264-P270-P280-P201-P202-P273-P301+P310-P330-P302+P352-P312-P361+P364-P308+P313-P391-P405-P501
Hazard Codes
T,N
Risk Statements
24 · 24/25-40-50/53
Safety Statements
22 · 22-36/37-45-60-61
RIDADR
2761 · 2761
OEB
E
OEL
0.001 mg/m3 · TWA: 0.001 mg/m3
RTECS
8575000 · PC8575000
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Hazardous Substances Data
143 · 143-50-0(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in rats: 125 mg/kg (Gaines)
Hazards Summary · 2 items

Mirex and chlordecone are two separate, but chemically similar, manufactured insecticides that do not occur naturally in the environment. Mirex is a white crystalline solid, and chlordecone is a tan-white crystalline solid. Both chemicals are odorless. Mirex and chlordecone have not been manufactured or used in the United States since 1978. Mirex was used to control fire ants, and as a flame retardant in plastics, rubber, paint, paper, and electrical goods from 1959 to 1972. Chlordecone was used as an insecticide on tobacco, ornamental shrubs, bananas, and citrus trees, and in ant and roach traps. Mirex was sold as a flame retardant under the trade name Dechlorane, and chlordecone was also known as Kepone. Use of trade names is for identification only and does not imply endorsement by the Agency for Toxic Substances and Disease Registry, the Public Health Service, or the U.S. Department of Health and Human Services.

In the past, workers in a manufacturing plant developed Kepone shakes with tremor, weakness, and slurred speech. Abnormal liver function tests were also seen. [Sullivan, p. 1078-9] Workers had decreased sperm counts. There is strong positive data and limited negative data that chlordecone causes fetal loss in animals. [ATSDR Case Studies #29]

Reactive GroupHalogenated Organic Compounds
EC ClassificationSymbol: T, N; R: 24/25-40-50/53; S: (1/2)-22-36/37-45-60-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
Special Reports · 5 items

Guzelian PS; Annu Rev Pharmacol Toxicol 22: 89-113 (1982). The comparative toxicology of chlordecone in humans and experimental animals is discussed.

WHO/International Programme on Chemical Safety; Environmental Health Criteria 43, Chlordecone (1984)[Available from, as of December 14, 2016: http://www.inchem.org/pages/ehc.html]

USEPA/OHEE; Kepone /Mirex/ Hexachlorocyclopentadiene: An Environmental Assessment. (1978) EPA Contract No. 68-01-3253

Benet H, et al; Neurotoxicology 6 (1): 151-8 (1985). A review on the neurotoxicity of chlordecone with emphasis on the basal ganglia of the brain.

For more Special Reports (Complete) data for Kepone (10 total), please visit the HSDB record page.

RCRA Requirements · 1 item

U142; As stipulated in 40 CFR 261.33, when chlordecone as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Safety & protection

Fire Fighting · 2 items

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give a slurry of activated charcoal in water to drink. Refer for medical attention .

First Aid · 2 items

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

Safe StorageProvision to contain effluent from fire extinguishing. Separated from acids.
Exposure Control and Personal Protection · 1 item

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Fire Fighting Procedures · 3 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use dry chemical, carbon dioxide, halon, water spray, or standard foam. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.

Storage Conditions · 3 items

Keep container tightly closed in a dry and well-ventilated place.

Store in a secure poison location. ... A regulated, marked area should be established where this chemical is handled, used, or stored in compliance with OSHA Standard 1910.1045. Store in a cool, dry place in a refrigerator under inert atmosphere. Keep away from acids and acid fumes.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practicable to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Cleanup Methods · 4 items

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Do not touch spilled material. Use water spray to reduce vapors. Evacuate persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. For larger spills, dike far ahead of spill for later disposal. Ventilate area after cleanup is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.

Survey reports six case histories employing EPA's hazardous materials spills treatment trailer are reviewed. The trailer's ... treatment system has three mixed-media filters and three activated carbon columns to remove suspended, precipitated, and organic soluble materials. Spills of PCB, pentachlorophenol, kepone, termide (chlordane), heptachlor, aldrin, and dieldrin, toxaphene, and dinitrobutylphenol were treated by the EPA trailer, which was generally successful in mitigating environmental effects by filtering and carbon-adsorption. 90% removal was achieved for 21 of 23 compounds.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labeled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labeled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 5 items

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U142, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.

A process has been developed which effects chlordecone degradation by treatment of aqueous wastes with UV radiation in the presence of hydrogen in aqueous sodium hydroxide solution. Up to 95% decomposition was effected by this process. Chlordecine perviously presented serious disposal problems because of its great resistance to bio- and photodegradation in the environment. It is highly toxic to normally occurring degrading microorganisms. Although it can undergo some photodecomposition when exposed to sunlight to the dihydro compound (leaving a compound with 8 chloro substituents) that degradation product does not significantly reduce toxicity. Disposal by incineration with HCl scrubbing is recommended.

For more Disposal Methods (Complete) data for Kepone (15 total), please visit the HSDB record page.

Spillage Disposal · 1 item

Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal protection: P3 filter respirator for toxic particles.

Preventive Measures · 5 items

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

For more Preventive Measures (Complete) data for Kepone (20 total), please visit the HSDB record page.

Toxicology

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 3 items

Kepone was detected in the adipose tissue of humans that were not occupationally exposed(1), but no quantified amounts were reported. Southeastern USA, Feb, 1976, mothers milk, 200 samples, 4.5% pos, detected, not quantified(2,3). Concentration in blood of workers who manufacture kepone, 32 workers, 0.165-26 ppm(1). Kepone was found in 9 out of 298 samples of human milk with a relatively high detection limit (1 mg/kg)(3).

Of 216 blood samples obtained from healthy members of the general population living within a one mile radius of a kepone manufacturing facility, 40 were found to contain detectable amounts of kepone ranging from 0.005-0.033 mg/L. ... Serum concentrations of kepone in 11 occupationally exposed subjects ranged from 0.120 - 2.109 mg/L and average 0.734 mg/L. The average serum half-life was found to be 96 days and the average blood/serum concentration ratio, 0.57.

Kepone was found present in blood and biopsy tissues of 32 chemical workers exhibiting symptoms of toxicity; average: 5.8 mg/l (blood), 76 mg/kg (liver), 22 mg/kg (fat).

TreatmentTreatment of chlordecone exposure is symptomatic. (L603)
Cancer Sites · 2 items

Hepatic

[in animal: liver cancer]

Interactions · 5 items

A series of psychopharmacological agents were administered to adult male Fischer-344 rats pretreated with a tremorigenic dose of chlordecone in an attempt to elucidate the involvement of spinal and supraspinal processes in the mediation and/or expression of chlordecone-induced tremor. Agents effective in attenuating the frequency of tremor were chlordiazepoxide, muscimol, and mecamylamine; Quipazine exacerbated the tremor. Catecholaminergic agents did not affect the frequency of chordecone-induced tremor. ...

... Male Sprague Dawley rats (175-200 g) received a single ip dose of 1, 5, 10, 15, or 25 uL bromotrichloromethane/kg following a 15 day dietary pretreatment of 0 or 10 ppm chlordecone. With the exception of 1 uL/kg dose which had no effect, chlordecone-bromotrichloromethane combination resulted in potentiation of hepatotoxicity by all parameters examined. ...

Difluoromethylornithine, an inhibitor of ornithine decarboxylase (200-800 mg/kg, sc), to rats has no detectable behavioral effects using a battery of tests to assess sensorimotor function. In contrast, the induction of tremor by chlordecone, a neurotoxic agent that affects neuronal ionic processes, is significantly attenuated by pretreatment with difluromethylornithine. The effects of difluromethylornithine on chlordecone-induced tremor were reversed by pretreatment with putrescine. Difluromethylornithine had no effects on 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane, a tremorigen having a mechanism of action different from chlordecone. ...

Kepone ingestion increased sensitivity of liver and kidney to chloroform toxicity.

For more Interactions (Complete) data for Kepone (14 total), please visit the HSDB record page.

Target Organs · 2 items

Urinary

Eyes, skin, respiratory system, central nervous system, liver, kidneys, reproductive system

Health EffectsChlordecone damages the nervous system, skin, liver, and male reproductive system. Animal studies indicate that it may also have harmful kidney effects, developmental effects, and effects on the ability of females to reproduce. (L601)
Ecotoxicity Values · 5 items

EC50; Species: Chironomous, fourth instar; Conditions: static, 22 °C; Concentration: 320 ug/L for 48 hr (95% confidence limit: 220-450 ug/L) /Technical material, 90.7%; Effect: immobilization/

EC50; Species: Daphnia magna, first instar; Conditions: static, 17 °C; Concentration: 260 ug/L for 48 hr (95% confidence limit: 200-345 ug/L) /Technical material, 90.7%/

LC50; Species: Gammarus pseudolimnaeus (mature); Conditions: static, 17 °C; Concentration: 180 ug/L for 96 hr (95% confidence limit: 110-290 ug/L) /Technical material, 90.7%/

LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout) weight 1.1 g; Conditions: static, 12 °C; Concentration: 30 ug/L for 96 hr (95% confidence limit: 24-38 ug/L) /Technical material, 90.7%/

For more Ecotoxicity Values (Complete) data for Kepone (26 total), please visit the HSDB record page.

Environmental Fate · 4 items

TERRESTRIAL FATE: Based on a classification scheme(1), experimentally-determined Koc values of 3330, 7440 and 15850(2,3) indicate that kepone is expected to be immobile in soil(SRC). Volatilization of kepone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.4X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-7 mm Hg(4), and water solubility of 2.7 mg/L(4). Kepone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. However, laboratory tests have measured small amounts of kepone volatilization from soil(4). Biodegradation of kepone can occur, but it is a very slow environmental process(5). A half-life of >312 days was measured using an estuarine sediment inoculum(6). Microbial mineralization of 14C-kepone was demonstrated in two tropical soils under aerobic conditions, but the rate of 14-CO2 evolution was only 3.2-4.9% after 215 days of incubation(2). Kepone may be susceptible to direct photolysis on soil surfaces exposed to sunlight(7). Monitoring data indicate kepone residues can exist in soil for years after pesticidal applications(2,5). Kepone is a persistent organochlorine insecticide that still has an environmental impact decades after its ban(2).

AQUATIC FATE: Based on a classification scheme(1), experimentally-determined Koc values of 3330, 7440 and 15850(2,3) indicate that kepone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 5.4X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-7 mm Hg(5), and water solubility of 2.7 mg/L(5). According to a classification scheme(6), a mean BCF range of 900-9,354(7), suggests the potential for bioconcentration in aquatic organisms is high to very high(SRC). Biodegradation of kepone can occur, but it is a very slow environmental process(8). Little to no biodegradation was observed in studies using activated sludge(9), contaminated hydrosoils(10), or exposure to sea water(11). A half-life of >312 days was measured using an estuarine sediment inoculum(12). Slow mineralization of kepone (3.2-4.9% CO2 evolution over 215 days of incubation) has been observed in aerobic soil studies(13). Kepone hydrates in aqueous solution to form the gem-diol kepone hydrate(14); the reaction is reversible(14).

AQUATIC FATE: ... Kepone and mirex are among the most stable pesticides in the aquatic environment. After 56 days of incubation under both aerobic and anaerobic conditions, there was no evidence of degradation of these two compounds.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), kepone, which has a vapor pressure of 2.25X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. The rate constant for the vapor-phase reaction of kepone with photochemically-produced hydroxyl radicals has been estimated as 0.0 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(3) indicating it is not expected to be an important fate process(SRC). However, kepone readily forms hydrates on exposure to ordinary temperatures and humidities(4). Vapor-phase kepone hydrate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 38 days(SRC), calculated from its rate constant of 2.8X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase kepone may be removed from the air by wet and dry deposition(SRC). Kepone and kepone hydrate are susceptible to direct photolysis by sunlight(5,6).

Food Survey Values · 1 item

Kepone was detected as a contaminant in studies conducted by the FDA from 1978-1982 and 1983-1986 on domestic and imported foods(1,2). A separate study in 1991 found one of the 13,085 food samples to contain detectable amounts of kepone(3). Kepone use in banana plantations in the French West Indies was banned in 1993, but kepone is still being detected in French West Indies foodstuffs (yam, dasheen, sweet potato, cucumber and pumpkin) decades later(4).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 3 items

The substance can be absorbed into the body through the skin, by ingestion and by inhalation.

inhalation, skin absorption, ingestion, skin and/or eye contact

Oral(L601) ; inhalation (L601) ; dermal (L601).

Regulatory information

RCRA Requirements · 1 item

U142; As stipulated in 40 CFR 261.33, when chlordecone as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

FIFRA Requirements · 2 items

Pesticide and Review Criteria Possibly Met or Exceeded: Carcinogenicity; Cancellations Issued Prior to Rebuttable Presumption Against Registration/Special Review Process.

All registered products containing kepone were effectively cancelled May 1, 1978. A summary of Kepone products, their registration numbers, effective cancellation dates, and disposition of uses of existing stocks follows: 1. Inaccessible Products: Antrol Ant Trap, Reg No 475-11; Black Flag Ant Trap, Reg No 475-82; Grant's Ant Trap, Reg No 1663-21; Grant's Roach Trap, Reg No 1663-22; Grant's Ant Control, Reg No 1663-24; and Dead Shot Ant Killer, Reg No 274-23 were cancelled as of May 11, 1977. Distribution, sale, and use of existing stocks formulated prior to May 11, 1977 was permitted until such stocks were exhausted. Black Leaf Ant Trap, Reg No 5887-63; Hide Roach and Ant, Reg No 3325-4; Lilly's Ant Trap with Kepone, Reg No 460-17; TNT Roach and Ant Killer, Reg No 2095-2; Johnston's No-Roach Traps, Reg No 2019-19; Mysterious Ant Trap with Kepone, Reg No 395-19; Magikill Ant Trap with Kepone, Reg No 395-21; Magikil Roach trap with Kepone, Reg No 395-25; Ant-Not Ant Trap, Reg No 358-20; Nott Roach Trapp, Reg No 358-129; E-Z Ant Trap Contains Kepone, Reg No 506-109; Tat Ant Trap, Reg No 506-126; and Ant Check Ant Trap, Reg No 506-129 were effectively cancelled on May 1, 1978. Distribution, sale, and use of Kepone products formulated prior to May 1, 1978 was permitted until such stocks were exhausted. 2. Accessible Products: All of these products were cancelled as of December 13, 1977. Distribution, sale, and use of these products is now unlawful. Inaccessible Products: included those which enclosed Kepone traps made from metal or plastic as well as metal stakes containing enclosed Kepone bait which are hammered into the ground. Accessible Products: Included those which, in normal use, would be removed from their containers, as well as foil or cardboard covered traps.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 1 item

Kepone is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

Safety data

OEB
E
OEL
TWA: 0.001 mg/m3
rtecs
PC8575000
ridadr
2761
Toxicity
LD50 orally in rats: 125 mg/kg (Gaines)
risk_code
24/25-40-50/53
Signal word
Danger
Symbol(GHS)
GHS06,GHS08,GHS09
hazard_code
T,N
safety_code
22-36/37-45-60-61
hazard_class
6.1(b)
packing_group
III
Hazard statements
H301-H311-H351-H410
Precautionary statements
P264-P270-P280-P201-P202-P273-P301+P310-P330-P302+P352-P312-P361+P364-P308+P313-P391-P405-P501
Hazardous Substances Data
143-50-0(Hazardous Substances Data)

Male Sprague Dawley rats were fed with chlordecone by gastric intubation at 10, 25, and 50 mg/kg/day for 3 days. Control rats received 0.3 mL of corn oil. Complete body movements (including tremors) were monitored for a period of 12 hr, and at 24, 48, and 72 hr after treatment. Rats receiving chlordecone showed an increased tremor activity which was significant and dose dependent. The brain synaptosomal sodium-potassium ion and oligomycin sensitive magnesium ion ATPases were significantly decreased in chlordecone treated rats. A linear relationship was observed between the decreases in ATPase activities and tremor activity. These results suggest that the inhibition of the ATPase system in the brain may be related to the production of the neurotoxic symptoms.

Biological Half-Life · 5 items

In humans, chlordecone is absorbed and distributed to various tissues and has a long retention time in the body. Chlordecone was eliminated slowly from the blood (half-life of 165 days) and fat (half-life of 125 days) of industrial workers. With cholestyramine treatment, blood half-life: 80 + or - 4 days, fat half-life: 64 days.

In rats exposed to a single oral dose of 40 mg/kg chlordecone, the blood half-lives at 4, 8, and 14 weeks were 8.5, 24, and 45 days, respectively.

... A kinetic study involving the contamination of laying hens (22 weeks of age) with a diet containing 500 ug chlordecone/kg during 42 d, followed by a depuration period of 35 d was carried out. ... The depuration half-life of chlordecone in liver, egg, abdominal fat and serum was estimated at 5.0 +/- 0.38 (mean +/- SE), 5.5 +/- 0.29, 5.3 +/- 0.37 and 5.1 +/- 0.66 d, respectively. ...

Chlordecone is an organochlorine insecticide which intoxicated a number of workers in 1975 because of excessive exposure in the industrial plant. The major manifestations were tremor, opsoclonus, arthralgias, pleural pain, and reduced sperm count. The half-life in blood was determined to be 165 days, but treatment with cholestyramine reduced this to 80 days. Despite initial high blood levels of chlordecone, follow up at six years indicated that in the workers reevaluated the chlordecone had been cleared completely from blood, with very low levels remaining in fat. As the chlordecone was cleared, the clinical manifestations abated, and many of the patients returned to work. ...

Rats received a single, oral, 40-mg/kg dose of (14)C-labeled chlordecone in a corn-oil solution. ... The blood half-life was 8.5 days for the first 4 weeks, 24 days for the next 8 weeks, and 45 days for the final 14 weeks. ...

Metabolism/Metabolites · 5 items

The fate of chlordecone in humans involves uptake by the liver, enzymatic reduction to chlordecone alcohol, conjugation with glucuronic acid, partial conversion to unidentified polar forms, and excretion of these metabolites mainly as glucuronide conjugates into bile. Of the total chlordecone measured in bile of occupationally exposed workers, the predominant portion (72%) was unconjugated, with only a small portion conjugated with glucuronic acid or sulfate (9%). The remaining fraction (19%) of total chlordecone measured in the bile was stable polar metabolites which were resistant to beta-glucuronidase. Following treatment of bile with beta-glucuronidase plus sulfatase, the ratio of total chlordecone to total chlordecone alcohol was 1:3 in human bile.

In seeking a practical animal model only in gerbils was this organochlorine pesticide converted to chlordecone alcohol, a reduced metabolite found in the stool of chlordecone poisoned humans. Gerbils eliminated chlordecone alcohol exclusively in stool with none being detected in urine. Gerbils excreted chlordecone alcohol in bile in an amount more than twice that of chlordecone and in the form of a glucuronide conjugate. The ratio of chlordecone to chlordecone alcohol in gerbil stool was 10 times higher than the ratio in human stool. This suggests that the newly recognized nonbiliary mechanism(s) for entry of chlordecone into the intestinal lumen may be extremely active in the gerbil. Incubation of the cytosolic fraction of gerbil liver homogenate in the presence of reduced nicotinamide adenine dinucleotide and chlordecone produced chlordecone alcohol. Bioreduction of chlordecone is catalyzed in gerbil liver by a species-specific reductase. The livers of these (3)H-chlordecone alcohol treated animals also contained chlordecone in amounts eight times (rat) and 14 times (gerbil) higher than the respective amounts of chlordecone alcohol. From this result, the existence of a separate enzyme(s) catalyzing dehydrogenation of chlordecone alcohol to chlordecone may be inferred.

...The conjugate of decachlorooctahydro 1,3,4-metheno-2H-cyclobuta(c,d)pentalen-2-ol (chlordecone alcohol) in fecal specimens from patients diagnosed as suffering from Kepone poisoning. This metabolite is a result of reduction of the ketonic group by an aldo-keto reductase enzyme that was identified in the gerbil, rabbit, and human but not in rodents.

... Pigs were administered chlordecone by intraperitoneal injection. Plasma, gall bladder bile, hepatic bile, liver, and feces were collected and analyzed by gas chromatography for chlordecone metabolites. Chlordecone alcohol was present in bile and feces with up to 85% conjugated in the bile but only 15% was conjugated in the feces. Up to 20% of the chlordecone in plasma and bile and less than 3% in feces was in the conjugated form. Both reduction and conjugation of chlordecone in the pig are similar to those in man.

Chlordecone is well absorbed orally and through inhalation, but may also be absorbed dermally to a lesser extent. It is widely distributed throughout the body and concentrates in the liver, where it is metabolized to chlordecone alcohol by chlordecone reductase. Chlordecone, chlordecone alcohol, and their glucuronide conjugates are slowly excreted in the bile and eliminated in the feces. (L601)

MeSH Pharmacological ClassificationPesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Absorption, Distribution and Excretion · 5 items

Kepone is absorbed from the GI tract and by way of the lungs and skin. It is retained primarily in the liver but also in the brain, kidneys, and fat.

Tissue-to-blood ratios for the liver, fat, muscle, and gallbladder bile were 15, 6.7, 2.9, and 2.5, respectively. The high concentration in blood as compared to its concentration in fat (1 versus 6.7) may be explained by the fact that chlordecone is bound specifically by the proteins in plasma, particularly high-density lipoproteins (HDLs), unlike most organochlorine pesticides which distribute among tissues in direct proportion to the concentration of tissue fat.

Chlordecone was present in high concentrations in the liver (mean and range) (75.9 mg/kg; 13.3 - 173 mg/kg), whole blood (5.8 mg/L, 0.6 - 32 mg/L), and subcutaneous fat (21.5 mg/kg, 2.2 - 62 mg/kg) of 32 male workers. ... In occupationally-exposed workers, serum chlordecone concentrations ranged from 120 to 2109 ug/L. Six to 7 months later, the concentration dropped to 37 - 486 ug/L.

In rats, chlordecone was absorbed and distributed to various tissues, with the highest concentrations being found in the liver. Chlordecone was detected in the liver (125.8 mg/kg), adipose tissue (27.3 mg/kg), kidney (25.2 mg/kg), and plasma (4.9 mg/L) of rats 8 days following a single oral dose of 50 mg/kg.

For more Absorption, Distribution and Excretion (Complete) data for Kepone (25 total), please visit the HSDB record page.

Cellular LocationsMembrane

Uses & manufacturing

Uses · 6 items

Formerly used as an insecticide; Base material for the manufacture of kelevan; [HSDB]

In 1975 the sole manufacturer of Kepone in the U.S. was ordered to terminate production. [Sullivan, p. 1048-9]

For chlordecone (USEPA/OPP Pesticide Code: 027701) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Formerly as insecticide, fungicide, miticide.

INSECTICIDE FOR BANANAS, NON-BEARING CITRUS TREES (FORMER USE), TOBACCO (FORMER USE), ORNAMENTAL SHRUBS, INSECTS IN BUILDINGS (FORMER USE), LAWNS, TURF, & FLOWERS (FORMER USE), INDOOR & OUTDOOR AREAS (FORMER USE)

Base material for the manufacture of kelevan.

U.S. Production · 3 items

(1978) NOT PRODUCED COMMERCIALLY IN USA

(1982) NOT PRODUCED COMMERCIALLY IN USA

Estimated average annual production before the shutdown of kepone was 882,000 pounds.

Methods of Manufacturing · 2 items

Preparation: Gilbert, Giolito, United States of America patent 2616825 and United States of America patent 2616928 (1952 to Allied Chem.); reissued as United States of America patent RE 24435 (1958).

Chlordecone is made by condensation of 2 mol of hexachlorocyclopentadiene in the presence of sulfur trioxide, followed by hydrolysis.

Formulations/Preparations · 2 items

Technical grade chlordecone contains from 88.6 to 99.4% chlordecone, 3.5-6.0% water and 0.1% hexachlorocyclopentadiene.

Chlordecone was avail in the USA until 1976 as a tech grade, typically containing 94.5% of the chemical (72.3% chlorine content), 0.30% methanol insolubles, 5.09% water, 0.01% sulfate, and 0.10% hexachlorocyclopentadiene.

Use Classification · 3 items

Chemical Classes -> Pesticides (chemicals used for killing pests, such as rodents, insects, or plants)

Food Contaminant -> CONTAMINANT; Food Contaminant -> -> JECFA Functional Classes

INSECTICIDES

General Manufacturing Information · 4 items

The WHO Recommended Classification of Pesticides by Hazard identifies Kepone as an active ingredient believed to be obsolete or discontinued for use as a pesticide.

Chlordecone is produced during the synthesis of Mirex.

Chlordecone is a ketone analog of mirex.

Discontinued 1977 by Allied Chem Corporation.

Applications · 5 items

DescriptionChemically, kepone is a chlorinated polycyclic insecticide and fungicide. Chlordecone was used as an insecticide for leaf-eating insects, ants, and cockroaches; as a larvicide for flies; and for control of insects that attack structures. Chlordecone was also used on bananas, nonbearing citrus trees, tobacco, ornamental shrubs, lawns, turf, and flowers. The dry powder is readily absorbed through the skin and respiratory tract. Occupational workers handling kepone without appropriate workplace safety dress and PPE suffered chemical poisoning. The symptoms included, tremors, jerky eye movements, memory loss, headaches, slurred speech, unsteadiness, lack of coordination, loss of weight, rash, enlarged liver, decreased libido, sterility, chest pain, and arthralgia (sharp pain, extending along a nerve or group of nerves, experienced in a joint and/or joints). Chlordecone was first introduced as a pesticide in 1958 and was used until 1978, when its use in the United States was discontinued (NCI 1976, IARC 1979, HSDB 2009).

UsesFormerly as insecticide, fungicide.

UsesInsecticide; fungicide.

UsesChlordecone, a chlorinated dicyclodiene compound, was introduced under the trade name Kepone in 1958. In the United States, Kepone found use as an ant and cockroach poison. Outside the United States, it was used primarily as a pesticide against the banana root borer. The compound is the ketone analog of mirex; it is a contaminant of mirex and is also a product of mirex degradation.

General DescriptionOdorless colorless crystalline solid.

Suppliers15 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海稳同科技有限公司02151600108 13062666369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
上海西陇生化科技有限公司021-52907766-8042
安泰精细化工技术有限公司18503026267 · [email protected]
山东小野化学股份有限公司0539-6362799 20)
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
上海泰坦科技股份有限公司13023226327 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
Aladdin Scientific[email protected]
青岛腾龙微波科技有限公司0532-83818797 17669478191 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]

Additional notes

DefinitionChEBI: An organochlorine compound with insecticidal activity.