Toxicokinetics of methyleugenol in F344 rats and B6C3F₁ mice

References

• Beroza M, Inscoe MN, Schwartz PH Jr, Keplinger ML, Mastri CW. (1975). Acute toxicity studies with insect attractants. Toxicol Appl Pharmacol 31:421–429.
   PubMed Web of Science ®Google Scholar
• Boberg EW, Miller EC, Miller JA, Poland A, Liem A. (1983). Strong evidence from studies with brachymorphic mice and pentachlorophenol that 1′-sulfoöxysafrole is the major ultimate electrophilic and carcinogenic metabolite of 1′-hydroxysafrole in mouse liver. Cancer Res 43:5163–5173.
   PubMed Web of Science ®Google Scholar
• Brennan RJ, Kandikonda S, Khrimian AP, DeMilo AB, Liquido NJ, Schiestl RH. (1996). Saturated and monofluoro analogs of the oriental fruit fly attractant methyl eugenol show reduced genotoxic activities in yeast. Mutat Res 369:175–181.
   PubMed Web of Science ®Google Scholar
• Buchanan RL. (1978). Toxicity of spices containing methylenedioxylbenzene derivatives: A review. J Food Safety 1:275–293.
   Google Scholar
• Burkey JL, Sauer JM, McQueen CA, Sipes IG. (2000). Cytotoxicity and genotoxicity of methyleugenol and related congeners – a mechanism of activation for methyleugenol. Mutat Res 453:25–33.
   PubMed Web of Science ®Google Scholar
• Carlini EA, de Oliveira AB, de Oliveira GG. (1983). Psychopharmacological effects of the essential oil fraction and of the hydrolate obtained from the seeds of Licaria puchury-major. J Ethnopharmacol 8:225–236.
   PubMedGoogle Scholar
• Chan VS, Caldwell J. (1992). Comparative induction of unscheduled DNA synthesis in cultured rat hepatocytes by allylbenzenes and their 1′-hydroxy metabolites. Food Chem Toxicol 30:831–836.
   PubMed Web of Science ®Google Scholar
• Chieco P, Moslen MT, Reynolds ES. (1981). Effect of administrative vehicle on oral 1,1-dichloroethylene toxicity. Toxicol Appl Pharmacol 57:146–155.
   PubMed Web of Science ®Google Scholar
• Code of Federal Regulations 21 ξ 121.1164.
   Google Scholar
• Dallmeier K, Carlini EA. (1981). Anesthetic, hypothermic, myorelaxant and anticonvulsant effects of synthetic eugenol derivatives and natural analogues. Pharmacology 22:113–127.
   PubMed Web of Science ®Google Scholar
• Davies B, Morris T. (1993). Physiological parameters in laboratory animals and humans. Pharm Res 10:1093–1095.
   PubMed Web of Science ®Google Scholar
• Deininger R, Wolfe E.. (1977). Treating muscle spasms. German Patent No. 2719623, 18/08/1977.
   Google Scholar
• Farnsworth NR. (1968). Hallucinogenic plants. Various chemical substances are known to be the active hallucinogenic principles in many plants. Science 162:1086–1092.
   PubMed Web of Science ®Google Scholar
• Flavor and Extract Manufacture Association of the United States (FEMA). (1978). Scientific literature review of eugenol and related substances in flavor usage. Vol. 1. Accession No. PB 283–501. Washington, DC: National Technical Information Service. US Department of Commerce.
   Google Scholar
• Furia TE, Bellanca N, Eds. (1975). Fenaroli’s handbook of flavor ingredients. 2nd ed. Vol. 2. Cleveland: The Chemical Rubber Co, 200.
   Google Scholar
• Fras I, Friedman JJ. (1969). Hallucinogenic effects of nutmeg in adolescent. N Y State J Med 69:463–465.
   PubMedGoogle Scholar
• Gardner I, Bergin P, Stening P, Kenna JG, Caldwell J. (1996). Immunochemical detection of covalently modified protein adducts in livers of rats treated with methyleugenol. Chem Res Toxicol 9:713–721.
   PubMed Web of Science ®Google Scholar
• Gingell R, Beatty PW, Mitschke HR, Page AC, Sawin VL, Putcha L, Kramer WG. (1987). Toxicokinetics of 1,2-dibromo-3-chloropropane (DBCP) in the rat. Toxicol Appl Pharmacol 91:386–394.
   Google Scholar
• Graves S. (1998). Determination of partition coefficient of methyleugenol. Special Task Report to NIEHS (NIH No. N01-ES-55395; G002840-UN).
   Google Scholar
• Howes AJ, Chan VS, Caldwell J. (1990). Structure-specificity of the genotoxicity of some naturally occurring alkenylbenzenes determined by the unscheduled DNA synthesis assay in rat hepatocytes. Food Chem Toxicol 28:537–542.
   PubMed Web of Science ®Google Scholar
• Ibrahim AG, Singh G, King HS. (1979). Trapping of the fruit flies, Dacus species (Diptera: Tephritidae) with methyleugenol in orchards. Pertanika 2:58–61.
   Google Scholar
• Jiang Y, Liu GQ, Ma JR, Xie L, Wu HQ. (1982). [The pharmacological studies on methyl-eugenol (author’s transl)]. Yao Xue Xue Bao 17:87–92.
   Google Scholar
• Johnson JD, Ryan MJ, Toft JD II, Graves SW, Hejtmancik MR, Cunningham ML, Herbert R, Abdo KM. (2000). Two-year toxicity and carcinogenicity study of methyleugenol in F344/N rats and B6C3F(1) mice. J Agric Food Chem 48:3620–3632.
   PubMed Web of Science ®Google Scholar
• Kettering JD, Torabinejad M. (1995). Investigation of mutagenicity of mineral trioxide aggregate and other commonly used root-end filling materials. J Endod 21:537–542.
   PubMed Web of Science ®Google Scholar
• Kim HJ, Bruckner JV, Dallas CE, Gallo JM. (1990). Effect of dosing vehicles on the pharmacokinetics of orally administered carbon tetrachloride in rats. Toxicol Appl Pharmacol 102:50–60.
   PubMed Web of Science ®Google Scholar
• MacGregor JT, Layton LL, Buttery RG. (1974). California bay oil. II. Biological effects of constituents. J Agric Food Chem 22:777–780.
   Google Scholar
• Meister RT. (1992). Farm Chemical Handbook. Willoughby: Meister Publishing Co., C221.
   Google Scholar
• Miller EC, Swanson AB, Phillips DH, Fletcher TL, Liem A, Miller JA. (1983). Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Res 43:1124–1134.
   PubMed Web of Science ®Google Scholar
• Mortelmans K, Haworth S, Lawlor T, Speck W, Tainer B, Zeiger E. (1986). Salmonella mutagenicity tests: II. Results from the testing of 270 chemicals. Environ Mutagen 8 Suppl 7:1–119.
   PubMedGoogle Scholar
• Moshonas MG, Shaw PE. (1978). Compounds new to essential orange oil from fruit treated with abscission chemicals. J Agric Food Chem 26:1288–1293.
   PubMed Web of Science ®Google Scholar
• National Academy of Sciences (NAS). (1989). 1987 poundage and technical effects update of substances added to food. Washington, DC: Committee on Food Additives Survey Data, Food and Nutrition Board, Institute of Medicine, National Academy of Sciences.
   Google Scholar
• National Institute for Occupational Safety and Health (NIOSH). (1990). National Occupation Exposure Survey (1981-1983). Unpublished provisional data as of July 1, 1990. Cincinnati: NIOSH.
   Google Scholar
• National Research Council. (1996). Guide for the care and use of laboratory animals. Washington, DC: National Academy Press.
   Google Scholar
• National Toxicology Program. (2000). Technical Report 491 on toxicology and carcinogenesis studies of methyleugenol (CAS No. 93-15-12) in F344/N rats and B6C3F1 mice (Gavage Studies). NIH Publication No. 98–3950. Research Triangle Park: US Department of Health and Human Services, Public Health Service, National Institutes of Health.
   Google Scholar
• Opdyke DLJ, Ed. (1979). Monographs on fragrance raw materials. New York: Pergamon Press Inc, 555.
   Google Scholar
• Phillips DH, Reddy MV, Randerath K. (1984). 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. II. Newborn male B6C3F1 mice. Carcinogenesis 5:1623–1628.
   PubMed Web of Science ®Google Scholar
• Renwick AG. (1994). Principles and methods of toxicology. 3rd edition. Hayes AW, ed. New York: Raven Press, 101–147.
   Google Scholar
• Schiestl RH, Chan WS, Gietz RD, Mehta RD, Hastings PJ. (1989). Safrole, eugenol and methyleugenol induce intrachromosomal recombination in yeast. Mutat Res 224:427–436.
   Google Scholar
• Sekizawa J, Shibamoto T. (1982). Genotoxicity of safrole-related chemicals in microbial test systems. Mutat Res 101:127–140.
   PubMed Web of Science ®Google Scholar
• Solheim E, Scheline RR. (1976). Metabolism of alkenebenzene derivatives in the rat. II. Eugenol and isoeugenol methyl ethers. Xenobiotica 6:137–150.
   PubMed Web of Science ®Google Scholar
• SRI International. (1990). Directory of chemical producers: United States of America. Menlo Park: SRI International, 654, 8, 291, 292, 391.
   Google Scholar
• Stofberg J, Grundschober F. (1987). Consumption ratio and food predominance of flavoring materials. Perfumer and Flavorist 12:27.
   Google Scholar
• Sticht RD, Smith RM. (1971). Eugenol: Some pharmacological observations. J Dent Res 50:1531–1535.
   PubMed Web of Science ®Google Scholar
• Weiss G. (1960). Hallucinogenic and narcotic-like effects of powdered Myristica (nutmeg). Psychiatr Q 34:346–356.
   PubMed Web of Science ®Google Scholar
• World Health Organization (WHO). (1981). Evaluation of certain food additives and contaminants. Twenty-sixth report of the Joint FAO/WHO Expert Committee on Food Additives. Technical Report Series 669. Geneva: WHO, 92–94.
   Google Scholar