Endrin Aldehyde Andrew Merwin
Chemical and Physical Properties • MW 381.9 g/mol • Solid • MP 145 – 149ºC • Kow 3.146, 4.7, 5.6 • Koc 4.80 • Vapor Pressure (25ºC) 2.0x10-7 mm Hg (EPA 1984)
Uses and Applications • Endrin Aldehyde - never commercially available • Bi-product of endrin ~ 0.05% • Minor product of photoisomerization of endrin ~9% (over 48hrs) • Endrin Ketone = major product • Endrin • Pesticide: Rodenticide, Insecticide, and avicide • Used from 1956 • Registered from Nov 17, 1971 – Sept 11, 1986 by Velsicol Chemical Company, Memphis, • Tennessee, • Toxicity to non-target raptors and migratory birds major reason for cancellation • 5.1-9.9 million pounded produced in 1962 alone. • May still be in use in other countries, however, Endrin is not required to be reported to the Toxic Release Inventory (TRI) so exported quantities are unknown.
Mode of Entry into Aquatic Env’t • No literature found for Endrin Aldehyde’s mode of entry • Most likely similar to Endrin • Sediment bound particles transported by rain or runoff • Volatilized or sediment bound particles dispersed by wind to surface water. • No significant leaching • Strongly adsorbs to sediment
Interactions with Water • Again, no studies found on Endrin Aldehyde, but by analogy with Endrin • Hydrolysis and Volatilization not major fates • Half life expected to be more than four years
Toxicity to (Aquatic) Life • No studies found on toxicity of endrin aldehyde to aquatic life • Lc50 for mice found to be > 500 mg/kg , although no experimental details were provided (Phillips et al., 1962) • Compared to Endrin’s 2.5 mg/kg (Walsh and Fink, 1972)
Toxic Effects • Although endrin effects the nervous system most notably, resulting in convulsions, no studies could be found on the neurological effects of endrin aldehyde. • Endrin aldehyde does, however, raise levels of serum glutamic oxaloacetic transaminase and glutamic pyruvic transaminase signifying acute liver damage. (Young, 1986)
Mode of Entry into Organisms • Because extremely hydrophobic, and strongly adsorbs to sediments, most likely effects benthic organisms through oral ingestion. • Bioconcentration considered probable fate (ATSDR 1996)
O H HO Molecular Mode of Interaction • Endrin is oxidized to syn and anit-12-hydroxyendrin by p450 • Followed by rapid dehydrogenation to 12-ketoendrin • Which non-competitively inhibits GABA, from GABA-gated Cl- channel (Wafford 1989). • Reducing inhibition of action potentials, resulting in convulsions.
Molecular Mode of Interaction • AGAIN, no studies found investigated the mode behind Endrin Aldehyde.
Biomolecular Mode of Breakdown • Major metabolites of endrin are syn and anti-12- hydroxyendrin as well as 12-ketoendrin. • No studies found listing metabolites of endrin aldehyde. Could potentially be oxidized by the same mechanism as endrin.
Detoxification • No data available
Bibliography • Agency for Toxic Substances and Disease Registry (ATSDR). 1996. Toxicological profile for Endrin. Atlanta, GA: U.S. Department of Health and Human Services, Public Health Service. • PETRELLA, V. (1977). IDENTIFICATION OF METABOLITES OF ENDRIN - METABOLISM IN ENDRIN SUSCEPTIBLE AND RESISTANT STRAINS OF PINE MICE. Journal of agricultural and food chemistry, 25(2), 393-398. • Phillips DD, Pollard GE, Soloway SB. 1962. Thermal isomerization of endrin and its behavior in gas chromatography. J Agric Food Chem 10(3):217-221. • WALSH, G. (1972). COMPARATIVE TOXICITY AND DISTRIBUTION OF ENDRIN AND DIELDRIN AFTER INTRAVENOUS ADMINISTRATION IN MICE. Toxicology and Applied Pharmacology, 23(3), 408-. • YOUNG, R. (1986). EFFECT OF ENDRIN AND ENDRIN DERIVATIVES ON HEPATOBILIARY FUNCTION AND CARBON TETRACHLORIDE-INDUCED HEPATOTOXICITY IN MALE AND FEMALE RATS. Food and Chemical Toxicology, 24(8), 863-868. • Wafford KA, Sattelle DB, Gant DB, et al. 1989. Noncompetitive inhibition of GABA receptors in insect and vertebrate CNS by endrin and lindane. Pesticide Biochem Physiol 33:213-219. • EPA. 1984. Analytical reference standards and supplemental data: The pesticides and industrial chemicals repository. U.S. Environmental Protection Agency, Environmental Monitoring Systems Laboratory - Las Vegas. EPA-600/4-84-082.