heptachlor epoxide


Summary: An oxidation product of HEPTACHLOR formed by many plants and animals, including humans, after exposure to HEPTACHLOR. It has been shown to remain in soil treated with HEPTACHLOR for over fifteen years and is toxic to animals and humans. (From ATSDR Public Heath Statement, April 1989)

Top Publications

  1. Hansen M, Matsumura F. Effects of heptachlor epoxide on components of various signal transduction pathways important in tumor promotion in mouse hepatoma cells. Determination of the most sensitive tumor promoter related effect induced by heptachlor epoxide. Toxicology. 2001;160:139-53 pubmed
    The effects of the organochlorine (OC) liver tumor promoter heptachlor epoxide (HE; 0, 0...
  2. Gao J, Liu L, Liu X, Lu J, Zhou H, Huang S, et al. Occurrence and distribution of organochlorine pesticides - lindane, p,p'-DDT, and heptachlor epoxide - in surface water of China. Environ Int. 2008;34:1097-103 pubmed publisher
    ..for the representative organochlorine pesticides contaminants including lindane (gamma-HCH), p,p'-DDT and heptachlor epoxide. In general, the most frequently detected compound was lindane, being detected in 83.9% of samples (mean=31...
  3. Pierik F, Klebanoff M, Brock J, Longnecker M. Maternal pregnancy serum level of heptachlor epoxide, hexachlorobenzene, and beta-hexachlorocyclohexane and risk of cryptorchidism in offspring. Environ Res. 2007;105:364-9 pubmed
    ..We examined the relation between serum levels of the pesticides heptachlor epoxide (HCE), hexachlorobenzene (HCB), and beta-hexachlorocyclohexane (beta-HCCH) in pregnant women, and the ..
  4. Cassidy R, Natarajan S, Vaughan G. The link between the insecticide heptachlor epoxide, estradiol, and breast cancer. Breast Cancer Res Treat. 2005;90:55-64 pubmed
    ..Other cyclodienes such as heptachlor epoxide (HE) and oxychlordane (OC) present in breast tissue have not been evaluated as rigorously, presumably due to ..
  5. Sharma C, Rosseland B, Almvik M, Eklo O. Bioaccumulation of organochlorine pollutants in the fish community in Lake Arungen, Norway. Environ Pollut. 2009;157:2452-8 pubmed publisher
    ..were dichlorodiphenyltrichloroethane (DDTs), polychlorinated biphenyls (PCBs), hexachlorobenzene (HCB), and heptachlor epoxide (HCE). DDTs were the dominant among all analyzed OCs...
  6. Baker D, Loo S, Barker J. Evaluation of human exposure to the heptachlor epoxide contamination of milk in Hawaii. Hawaii Med J. 1991;50:108-12, 118 pubmed
    The commercial milk supply on Oahu was contaminated by heptachlor epoxide for as long as 15 months during 1981-82 at levels possibly as high as 1.2 ug/g, fat basis...
  7. Pfaffenberger B, Hardt I, Hühnerfuss H, Konig W, Rimkus G, Glausch A, et al. Enantioselective degradation of alpha-hexachlorocyclohexane and cyclodiene insecticides in roe-deer liver samples from different regions of Germany. Chemosphere. 1994;29:1543-54 pubmed
  8. Hickey J, Batterman S, Chernyak S. Trends of chlorinated organic contaminants in great lakes trout and walleye from 1970 to 1998. Arch Environ Contam Toxicol. 2006;50:97-110 pubmed
  9. Harper R, Frick J, Capparella A, Borup B, Nowak M, Biesinger D, et al. Organochlorine pesticide contamination in neotropical migrant passerines. Arch Environ Contam Toxicol. 1996;31:386-90 pubmed
    ..Eighteen of the 19 birds contained p,p'-DDE, while dieldrin was found in 16 birds and heptachlor epoxide was present in 10 birds...

More Information


  1. Luderer U, Kesner J, Fuller J, Krieg E, Meadows J, Tramma S, et al. Effects of gestational and lactational exposure to heptachlor epoxide on age at puberty and reproductive function in men and women. Environ Res. 2013;121:84-94 pubmed publisher
    For 15 months in 1981-1982, the commercial milk supply on the Hawaiian island of Oahu was contaminated with heptachlor epoxide, a metabolite of the insecticide heptachlor, resulting in gestational and/or lactational exposure to offspring ..
  2. Smialowicz R, Williams W, Copeland C, Harris M, Overstreet D, Davis B, et al. The effects of perinatal/juvenile heptachlor exposure on adult immune and reproductive system function in rats. Toxicol Sci. 2001;61:164-75 pubmed
    ..Some dams and PND 7 pups were euthanized; milk, plasma, fat and/or tissues were assayed for H and heptachlor epoxide B (HEB), a major metabolite of H...
  3. Hansen M, Matsumura F. Down-regulation of particulate protein kinase Cepsilon and up-regulation of nuclear activator protein-1 DNA binding in liver following in vivo exposure of B6C3F1 male mice to heptachlor epoxide. J Biochem Mol Toxicol. 2001;15:1-14 pubmed
    The effects of in vivo administration of the cyclodiene tumor promoter heptachlor epoxide on mouse liver protein kinase C were studied in male B6C3F1 mice by protein kinase C activity assays and Western blotting under conditions known to ..
  4. Champion W, Lee J, Garrison A, DiMarco J, Matabe A, Prickett K. Liquid chromatographic separation of the enantiomers of trans-chlordane, cis-chlordane, heptachlor, heptachlor epoxide and alpha-hexachlorocyclohexane with application to small-scale preparative separation. J Chromatogr A. 2004;1024:55-62 pubmed
    ..The enantiomers of the heptachlor metabolite, heptachlor epoxide, were separated on CHIRALPAK AD using a methanol mobile phase...
  5. Cassidy R, Vaughan G, Pruitt B, Mason A. Xenoestrogens: do they lower survival after thermal injury?. Arch Environ Health. 2003;58:597-604 pubmed
    The effect of hormone disruptors on human health is an area of recent concern. The authors measured heptachlor epoxide and oxychlordane--the body storage forms of estrogenic insecticides-in the sera of patients with major burns (i.e...
  6. Schenck F. Screening of nonfatty fish for organochlorine pesticide residues by solid-phase extraction cleanup: interlaboratory study. J AOAC Int. 1996;79:1215-9 pubmed
    ..The participants analyzed control and fortified (about 0.050 ppm lindane, heptachlor epoxide, p,p'-DDE, and endrin) croaker and flounder samples and a sea trout sample containing incurred p,p'-DDE ..
  7. Nomata K, Kang K, Hayashi T, Matesic D, Lockwood L, Chang C, et al. Inhibition of gap junctional intercellular communication in heptachlor- and heptachlor epoxide-treated normal human breast epithelial cells. Cell Biol Toxicol. 1996;12:69-78 pubmed
    ..in human tissue, this study was designed to determine whether various noncytotoxic levels of heptachlor and heptachlor epoxide could inhibit, reversibly, gap junctional intercellular communication in human breast epithelial cells (HBEC)..
  8. Matesic D, Rupp H, Bonney W, Ruch R, Trosko J. Changes in gap-junction permeability, phosphorylation, and number mediated by phorbol ester and non-phorbol-ester tumor promoters in rat liver epithelial cells. Mol Carcinog. 1994;10:226-36 pubmed
    ..12-O-tetradecanoylphorbol-13-acetate (TPA; 10 ng/mL), dieldrin (10 micrograms/mL), and heptachlor epoxide (10 micrograms/mL) inhibited gap-junctional intercellular communication (GJIC) assayed by fluorescent dye ..
  9. Petterson D, Casey R, Ebell G, McIntyre B. Residues in beef cattle accidentally exposed to commercial heptachlor. Aust Vet J. 1988;65:50-3 pubmed
    The changes in concentration of heptachlor epoxide (HCE) and oxychlordane (OCD) were studied in the tissues of beef cattle that had previously grazed pasture contaminated with commercial heptachlor...
  10. Adeshina F, Todd E. Organochlorine compounds in human adipose tissue from north Texas. J Toxicol Environ Health. 1990;29:147-56 pubmed
    ..presence of beta-benzene hexachloride, o,p'-DDE, p,p'-DDE, o,p'-DDT, p,p'-DDT, dieldrin, oxychlordane, and heptachlor epoxide. The findings indicate greater than 97% occurrence for each compound with the exception of o,p'-DDE and o,p'-..
  11. Bandala E, Andres Octaviano J, Pastrana P, Torres L. Removal of aldrin, dieldrin, heptachlor, and heptachlor epoxide using activated carbon and/or Pseudomonas fluorescens free cell cultures. J Environ Sci Health B. 2006;41:553-69 pubmed
    ..and heptachlor epoxide (1aalpha, 1bbeta,2alpha,5alpha,5alphabeta,6beta,6aalpha-2,3,4,5,6,7,7-Heptachloro-1a,1b,5,5a,6,6a-hexahydro-..
  12. Hansen M, Pessah I, Matsumura F. Heptachlor epoxide induces a non-capacitative type of Ca2+ entry and immediate early gene expression in mouse hepatoma cells. Toxicology. 2006;220:218-31 pubmed
    The effects of the organochlorine (OC) liver tumor promoter heptachlor epoxide (HE) and a related non-tumor promoting OC, delta-hexachlorocyclohexane (delta-HCH), on the dynamics of intracellular calcium (Ca2+) were investigated in mouse ..
  13. Flores B, Camarena C, Ren J, Krishnamurthy S, Belzer W. Assessment of organochlorine pesticide levels in Manadas Creek, an urban tributary of the Rio Grande in Laredo, Texas. Arch Environ Contam Toxicol. 2009;57:11-20 pubmed publisher
    ..collected, several organochlorine pesticides including alpha-, beta-, and gamma-hexachlorocyclohexane (HCH), heptachlor epoxide, endrin, and 4,4'-DDT were found in either the creek water or sediments...
  14. Beyer W, Gale R. Persistence and changes in bioavailability of dieldrin, DDE, and heptachlor epoxide in earthworms over 45 years. Ambio. 2013;42:83-9 pubmed publisher
    The finding of dieldrin (88 ng/g), DDE (52 ng/g), and heptachlor epoxide (19 ng/g) in earthworms from experimental plots after a single moderate application (9 kg/ha) 45 years earlier attests to the remarkable persistence of these ..
  15. Hegeman W, Laane R. Enantiomeric enrichment of chiral pesticides in the environment. Rev Environ Contam Toxicol. 2002;173:85-116 pubmed
    ..Environmental regulation authorities should treat chiral pesticides as a composition of enantiomers because biotic processes handle enantiomers as separate chemical entities. ..
  16. Singh G, Dowman A, Higginson F, Fenton I. Translocation of aged cyclodiene insecticide residues from soil into forage crops and pastures at various growth stages under field conditions. J Environ Sci Health B. 1992;27:711-28 pubmed
    ..Substantial amounts of heptachlor epoxide, and lesser amounts of gamma-chlordane were translocated to plants from contaminated soil...
  17. van Wyk E, Bouwman H, van der Bank H, Verdoorn G, Hofmann D. Persistent organochlorine pesticides detected in blood and tissue samples of vultures from different localities in South Africa. Comp Biochem Physiol C Toxicol Pharmacol. 2001;129:243-64 pubmed
    ..This includes residues of gamma-BHC, alpha-chlordane, dieldrin, beta-endosulfan and heptachlor epoxide. Values of the respective biocides measured in vulture samples were generally low in comparison to results ..
  18. Miller G, Kirby M, Levey A, Bloomquist J. Heptachlor alters expression and function of dopamine transporters. Neurotoxicology. 1999;20:631-7 pubmed
    ..In a DAT expressing cell line, acute treatment with the putative toxic species of heptachlor, heptachlor epoxide, did not alter plasma membrane dopamine uptake...
  19. Sim M, Forbes A, McNeil J, Roberts G. Termite control and other determinants of high body burdens of cyclodiene insecticides. Arch Environ Health. 1998;53:114-21 pubmed
    Breast milk fat concentrations of three cyclodiene insecticides--dieldrin, heptachlor epoxide, and oxychlordane--were measured in 797 primiparous women, and sources of exposure that contributed significantly to high body burdens were ..
  20. Waliszewski S, Pardio V, Waliszewski K, Chantiri J, Infanzon R, Rivera J. Detection of some organochlorine pesticides in cow's milk. Food Addit Contam. 1996;13:231-5 pubmed
    ..The results obtained for mean DDT and HCH levels were 0.057 and 0.098 mg/kg respectively expressed on fat basis and are within FAO tolerances and similar to those found in other tropical countries. ..
  21. Zaman S, Harvey R, Barnard E, Darlison M. Unusual effects of benzodiazepines and cyclodiene insecticides on an expressed invertebrate GABAA receptor. FEBS Lett. 1992;307:351-4 pubmed
    ..In addition, members of the cyclodiene class of insecticides block the channel of the receptor in a manner indistinguishable from that of picrotoxin. ..
  22. Xu R, Wu J, Liu Y, Zhao R, Chen B, Yang M, et al. Analysis of pesticide residues using the Quick Easy Cheap Effective Rugged and Safe (QuEChERS) pesticide multiresidue method in traditional Chinese medicine by gas chromatography with electron capture detection. Chemosphere. 2011;84:908-12 pubmed publisher
    ..OCPs were benzene hexachloride (BHC, including ?-BHC, ?-BHC, ?-BHC, ?-BHC), hexachlorobenzene, heptachlor, heptachlor epoxide, aldrin, p, p'-DDE, p, p'-DDD, o, p'-DDT, p, p'-DDT, mirex, endrin, dieldrin...
  23. Riget F, Bignert A, Braune B, Stow J, Wilson S. Temporal trends of legacy POPs in Arctic biota, an update. Sci Total Environ. 2010;408:2874-84 pubmed publisher
  24. Mussalo Rauhamaa H, Pyysalo H, Antervo K. Heptachlor, heptachlor epoxide, and other chlordane compounds in Finnish plywood workers. Arch Environ Health. 1991;46:340-6 pubmed
    Residue levels of heptachlor, heptachlor epoxide, and other chlordane compounds were determined in sera from 74 Finnish plywood workers and 52 controls...
  25. Spicer P, Kereu R. Organochlorine insecticide residues in human breast milk: a survey of lactating mothers from a remote area in Papua New Guinea. Bull Environ Contam Toxicol. 1993;50:540-6 pubmed
    ..96 mg/kg vs. .63;l p .05). 6 mothers had Heptachlor epoxide in their breast milk (.01-.02 mg/kg), but the levels were below the maximum residual concentration of ...
  26. Prado G, Bhalli J, Marcos R. Genotoxicity of heptachlor and heptachlor epoxide in human TK6 lymphoblastoid cells. Mutat Res. 2009;673:87-91 pubmed publisher
    The genotoxic potential of the organochlorine insecticides heptachlor (HC) and its metabolite heptachlor epoxide (HCE) has been evaluated in TK6 cells, a well-established human lymphoblastoid cell line...
  27. Xue J, Hao L, Peng F. Residues of 18 organochlorine pesticides in 30 traditional Chinese medicines. Chemosphere. 2008;71:1051-5 pubmed
    ..18 pesticides: benzene hexachloride (BHC, including alpha-BHC, beta-BHC, gamma-BHC, delta-BHC), heptachlor, heptachlor epoxide, tecnazene, pentachloronitrobenzene (PCNB), hexachlorobenzene, aldrin, methyl pentachlorophenyl sulphide (..
  28. Hayashi O, Kameshiro M, Satoh K. Degradation of the persistent organic pollutant [14C]heptachlor in Japanese field soils. Biosci Biotechnol Biochem. 2013;77:1240-4 pubmed
    ..Heptachlor was degraded mainly to cis-heptachlor epoxide by a biotic process and to 1-hydroxychlordene by an abiotic process in the field soils...
  29. Scherb H, Weigelt E, Oxynos K, Gebefugi I. [Organochlorine compounds in human milk]. Zentralbl Hyg Umweltmed. 1990;190:558-68 pubmed
    ..We therefore recommend that the pattern of OCC-correlations in human milk is further studied in more representative samples. These investigations should also comprise occupationally exposed women. ..
  30. Crum J, Aulerich R, Polin D, Braselton W, Bursian S. The efficacy of mineral oil combined with feed restriction in enhancing the elimination of heptachlor epoxide from mink (Mustela vison). Arch Environ Contam Toxicol. 1994;26:374-80 pubmed
    ..intake (MO/R) for 21 days to determine the efficacy of the latter treatment in enhancing the elimination of heptachlor epoxide (HE) from mink. Kit mink (2-3 months of age) whelped by dams of the control and 6...
  31. Hosie S, Loff S, Witt K, Niessen K, Waag K. Is there a correlation between organochlorine compounds and undescended testes?. Eur J Pediatr Surg. 2000;10:304-9 pubmed
  32. Ogata M, Izushi F, Eto K, Sakai R, Inoue B, Noguchi N. Effect of chlordane on hepatic mitochondrial respiration. Toxicol Lett. 1989;48:67-74 pubmed
    ..The release of K+ ions paralleled the results of the respiratory activity study. Heptachlorepoxide, a metabolic product of heptachlor, had less effect on mitochondria than heptachlor. ..
  33. Grynkiewicz M, Polkowska Z, Gorecki T, Namiesnik J. Pesticides in precipitation in the Gda?sk region (Poland). Chemosphere. 2001;43:303-12 pubmed
    ..11-5.80 ng/l), fenitrothion (0.1-2.10 ng/l), chlorfenvinfos (0.1-1.30 ng/l), gamma-HCH (0.012-5.06 ng/l), heptachlor epoxide (0.05-3.28 ng/l) and aldrin (0.02-3.28 ng/l)...
  34. Raum E, Seidler A, Schlaud M, Knoll A, Wessling H, Kurtz K, et al. Contamination of human breast milk with organochlorine residues: a comparison between East and West Germany through sentinel practice networks. J Epidemiol Community Health. 1998;52 Suppl 1:50S-55S pubmed
    ..No differences between the two states were found for PCB, HCB, gamma-HCH, and dioxin. Breast milk contamination levels in former East German Saxony-Anhalt exceeded the contamination in Lower Saxony only for DDT and beta-HCH. ..
  35. Xiao P, Mori T, Kamei I, Kondo R. Metabolism of organochlorine pesticide heptachlor and its metabolite heptachlor epoxide by white rot fungi, belonging to genus Phlebia. FEMS Microbiol Lett. 2011;314:140-6 pubmed publisher
    ..study, we evaluated the ability of 18 white rot fungi species of genus Phlebia to degrade heptachlor and heptachlor epoxide, and described the metabolic pathways by selected white rot fungi...
  36. O Hara T, Krahn M, Boyd D, Becker P, Philo L. Organochlorine contaminant levels in Eskimo harvested bowhead whales of arctic Alaska. J Wildl Dis. 1999;35:741-52 pubmed
    ..However, investigation of low level chronic exposure effects and a more rigorous assessment of histopathology, biomarkers, and immune status in the bowhead whale would be required to conclude "no effect" with more certainty. ..
  37. Garcia E, Baliwas B, Tran T, Assaf M, Bagri P, Woolley D. Opposite gender-specific increases in peripheral benzodiazepine receptor (PBR) expression in rat brain after single administration of the GABA antagonists heptachlor and heptachlor epoxide. Proc West Pharmacol Soc. 2003;46:54-7 pubmed
  38. Falandysz J. [The use amount of chlordane, heptachlor and heptachlor epoxide in Poland]. Rocz Panstw Zakl Hig. 2003;54:49-64 pubmed
    Chlordanes, heptachlor and heptachlor epoxide exposure from a particular food items in Poland in 1970-1996 was calculated by multiplying its annualized mean consumption rates by residue concentration in the food...
  39. Sahagún A, Teran M, Garcia J, Sierra M, Fernandez N, Diez M. Organochlorine pesticide residues in muscle tissue of rainbow trout, Oncorhynchus mykiss, taken from four fish farms in León, Spain. Food Addit Contam. 1998;15:501-5 pubmed
    Levels of nine organochlorine pesticides (lindane, heptachlor epoxide, aldrin, dieldrin, endrin, o,p'-TDE, p,p'-TDE, p,p'-DDE and p,p'-DDT) were determined in muscle samples of rainbow trout, Onchorhynchus mykiss, collected from four fish ..
  40. McManus S, Coxon C, Richards K, Danaher M. Quantitative solid phase microextraction - gas chromatography mass spectrometry analysis of the pesticides lindane, heptachlor and two heptachlor transformation products in groundwater. J Chromatogr A. 2013;1284:1-7 pubmed publisher
    ..for the determination of lindane, heptachlor and two heptachlor transformation products (exo- and endo-heptachlor epoxide) in groundwater...