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

Physical and Chemical Properties  White, Odorless, Crystalline Solid  Molecular Formula C 12 H 8 Cl 6 O  Melting Pt °C  Boiling Pt 245°C  Solubility in water Practically insoluble  Partition Coefficient Log K ow = 5.34  Structure

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%)

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

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

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

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 ContactInverts readily take up endrin

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

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

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

References  IPCS International Program on Chemical Safety Health and Safety Guide No  Toxicological Profile for Endrin. Agency for Toxic Substances and Disease Registry.  Technical Factsheet on: Endrin. US EPA.  Chemical: Endrin. Comparative Toxicogenomics Database 2A01BF1E1?type=chem&acc=D004732&view=ixn#g A01BF1E1?type=chem&acc=D004732&view=ixn#g  Guidelines for managing water quality impacts within UK European marine sites  Public Health Goal for Endrin In Drinking Water. CA EPA.