ENDRIN

1. ENDRIN Kevin McPeck Cal State University Long Beach Aquatic Toxicology Dr. Mason

2. White, Odorless, Crystalline Solid Molecular Formula C12H8Cl6O Melting Pt. 226-230°C Boiling Pt Decomposes @ 245°C Solubility in water Practically insoluble Partition Coefficient Log Kow = 5.34 Structure Physical and Chemical Properties

3. Uses, Application, Production History • Production began in the 50’s & use declined around the early 70’s • Severe restrictions on its use and is banned in many countries • In U.S., Vesicol Chemical Co. was last to abandon production in 1991 • Commercial availability: • Type of Products • Dust, Granules, Paste, Emulsifiable concentrate • Product Names • Mendrin, Hexadrin, Endrex, Nendrin • Organochloride Insecticide Used on: • Mainly on cotton • Rice, sugar cane, and maize • Also used as a rodenticide and avicide • One of the most hazardous compounds (top 10%)

4. Chemical Reactivity with Water, Chemical Speciation, Physical Half-Life • Solubility is extremely low (0.2 mg/L) • Quickly absorbs to sediment • Half Life (soils) - up to 12 years • Endrin aldehyde and endrin ketone • Occur as impurities of endrin or as the result of degradation • Known to photodegrade to delta-ketoendrin • Half-Life ~7days • Degraded at greater levels than dieldrin, aldrin

5. Mode of Entry to Aquatic Environment • Major Source of input is due to RUN-OFF • Effectively remains in soils that are high in organic content • Minor Entry Modes • Ariel application in areas near major water sources (no longer a problem) • Improper waste management / spillage

6. Toxicity to Aquatic Life • Bioconcentration Factor (BCF) ~ 1,335-10,000 in fish ~ 500-1250 shellfish ~ 49,000 snail • 96-hr LC50 for fish, marine inverts, phytoplankton • < 1.0g/L • LOEC for mysid shrimp • 30 ng/L

7. Mode of Entry into Organism • Fish • Direct Contact through gills and other exposed membranes if in areas of high run-off • Filter Feeders • Consumption due to binding affinity high concentrations exist in soil and particulate matter • Benthic Organisms • Direct Contact Inverts readily take up endrin

8. Toxic Effects • DEATH!!! • Endocrine disruption • Increase PKC activity • PKC linked to cell adhesion, cell transformation • Inhibit cell communication • Mimics epithelial growth factor genes • Growth factor vs. cell differentiation

9. Molecular Mode of Toxic Interaction • CYP450 Monooxygenase Reaction • CYP26A1 • CYP2B6 - All Increase in expression of gene • CYP3A4 • CEBPA – CCAAT/enhancer binding protein • Decreases activity in mice • ESR1- estrogen recptor • Increased activity in humans

10. Biochemical Metabolism and Breakdown • Animals rapidly metabolize endrin • Relatively low accumulation in fats (compared to similar structures dieldrin, aldrin) • Major of metabolism occurs at the methlyene bridge Becomes

11. References • IPCS International Program on Chemical Safety Health and Safety Guide No. 60 http://www.inchem.org/documents/hsg/hsg/hsg060.htm • Toxicological Profile for Endrin. Agency for Toxic Substances and Disease Registry. http://www.atsdr.cdc.gov/toxprofiles/tp89.html • Technical Factsheet on: Endrin. US EPA. http://www.epa.gov/OGWDW/dwh/t-soc/endrin.html • Chemical: Endrin. Comparative Toxicogenomics Database http://ctd.mdibl.org/detail.go;jsessionid=DC35F4D53B991EEE5B7D9322A01BF1E1?type=chem&acc=D004732&view=ixn#g318190 • Guidelines for managing water quality impacts within UK European marine sites http://www.ukmarinesac.org.uk/pdfs/water_quality.pdf • Public Health Goal for Endrin In Drinking Water. CA EPA. http://www.oehha.org/water/phg/pdf/endrin_f.pdf