Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 53, 2023 - Issue 5
66
Views
0
CrossRef citations to date
0
Altmetric
Animal Pharmacokinetics and Metabolism

Toxicokinetic and mass balance of morpholine in rats

, , , , , , & show all
Pages 412-420 | Received 05 May 2023, Accepted 05 Jul 2023, Published online: 17 Aug 2023

References

  • Akyüz M, Ata S. 2006. Simultaneous determination of aliphatic and aromatic amines in water and sediment samples by ion-pair extraction and gas chromatography-mass spectrometry. J Chromatogr A. 1129 (1):88–94. doi: 10.1016/j.chroma.2006.06.075.
  • Agence nationale de sécurité sanitaire de l’alimentation, de l’environnement et du travail (ANSES). 2012. AVIS relatif à l’évaluation des risques sanitaires liés à la présence de N-nitrosomorpholine dans l’eau destinée à la consommation humaine- Saisine n° 2012-SA-0172. Saisine(s) liée(s) n° 2012-SA-0181 et 2012-SA-0188.
  • Bartsch HE, Hietanen E, Malaveille C. 1989. Carcinogenic nitrosamines: free radical aspects of their action. Free Radic Biol Med. 7(6):637–644. doi: 10.1016/0891-5849(89)90144-5.
  • Bogovski P, Bogovski S. 1981. Animal species in which N-nitroso compounds induce cancer. Int J Cancer. 27(4):471–474. doi: 10.1002/ijc.2910270408.
  • Clapp R, Jacobs M, Lijinsky W. 2012. N-nitroso compounds. Patty’s toxicology, 6 Vol, 6th ed.
  • De Vocht F, Burstyn I, Straif K, Vermeulen R, Jakobsson K, Nichols L, Peplonska B, Taeger D, Kromhout H. 2007. Occupational exposure to NDMA and NMOR in the European rubber industry. J Environ Monit. 9(3):253–259. doi: 10.1039/b615472g.
  • Edwards G, Whong W-Z, Speciner N. 1979. Intrahepatic mutagenesis assay: a sensitive method for detecting N-nitrosomorpholine and in vivo nitrosation of morpholine. Mutat Res. 64 (6):415–423. doi: 10.1016/0165-1161(79)90111-0.
  • Flick AC, Ding HX, Leverett CA, Kyne RE, Liu KK-C, Fink SJ, O’Donnell CJ. 2016. Synthetic approaches to the 2014 new drugs. Bioorg Med Chem. 24(9):1937–1980. doi: 10.1016/j.bmc.2016.03.004.
  • Gushgari AJ, Halden RU. 2018. Critical review of major sources of human exposure to N-nitrosamines. Chemosphere. 210:1124–1136. doi: 10.1016/j.chemosphere.2018.07.098.
  • Hecht SS, Chen CH, McCoy GD, Hoffmann D, Domellöf L. 1979. Alpha-hydroxylation of N-nitrosopyrrolidine and N’-nitrosonornicotine by human liver microsomes. Cancer Lett. 8(1):35–41. doi: 10.1016/0304-3835(79)90020-x.
  • Hecht SS, Young R. 1981. Metabolic alpha-hydroxylation of N-nitrosomorpholine and 3,3,5,5-tetradeutero-N-nitrosomorpholine in the F344 rat. Cancer Res. 41(12 Pt 1):5039–5043.
  • Hecht SS, Morrison JB. 1984a. A sensitive method for detecting in vivo formation of N-nitrosomorpholine and its application to rats given low doses of morpholine and sodium nitrite. Cancer Res. 44(7):2873–2877.
  • Hecht SS, Morrison JB, Young R. 1984b. N-Nitroso(2-hydroxyethyl)glycine, a urinary metabolite of N,N-dinitrosopiperazine with potential utility as a monitor for its formation in vivo from piperazine. Carcinogenesis. 5(7):979–981. doi: 10.1093/carcin/5.7.979.
  • Herrmann SS. 2014. N-nitrosamines in processed meat products – analysis, occurrence, formation, mitigation and exposure. National Food Institute: Technical University of Denmark.
  • Iijima K, Grant J, McElroy K, Fyfe V, Preston T, McColl KEL. 2003. Novel mechanism of nitrosative stress from dietary nitrate with relevance to gastro-oesophageal junction cancers. Carcinogenesis. 24(12):1951–1960. doi: 10.1093/carcin/bgg168.
  • Li Y, Hecht SS. 2022. Metabolic activation and DNA interactions of carcinogenic N-nitrosamines to which humans are commonly exposed. Int. J. Mol. Sci. 23:4559. doi: 10.3390/ijms23094559.
  • Lim DS, Lim SK, Kim MK, Kwon YC, Roh TH, Choi SM, Yoon S, Kim N-H, Lee BM. 2018. Formation and inhibition of N-nitrosodiethanolamine in cosmetics under pH, temperature, and fluorescent, ultraviolet, and visual light. J Toxicol Environ Health A. 81(9):241–253. doi: 10.1080/15287394.2018.1440172.
  • Loh YH, Jakszyn P, Luben RN, Mulligan AA, Mitrou PN, Khaw KT. 2011. N-nitroso compounds and cancer incidence: the European Prospective Investigation into Cancer and Nutrition (EPIC)–Norfolk Study. Am J Clin Nutr. 93(5):1053–1061. doi: 10.3945/ajcn.111.012377.
  • Ma F, Wan Y, Yuan G, Meng L, Dong Z, Hu J. 2012. Occurrence and source of nitrosamines and secondary amines in groundwater and its adjacent Jialu river basin, China. Environ Sci Technol. 46 (6):3236–3243. doi: 10.1021/es204520b.
  • Mcguire RG, Hagenmaier RD. 1996. Shellac coatings for grapefruits that favor biological control of penicillium digitatumby Candida oleophila. Biol Control. 7(1):100–106. doi: 10.1006/bcon.1996.0071.
  • Mirvish SS. 1975. Formation of N-nitroso compounds: chemistry, kinetics, and in vivo occurrence. Toxicol Appl Pharmacol. 31(3):325–351. doi: 10.1016/0041-008x(75)90255-0.
  • Mitch WA, Sedlak DL. 2004. Characterization and fate of N-nitrosodimethylamine precursors in municipal wastewater treatment plants. Environ Sci Technol. 38(5):1445–1454. doi: 10.1021/es035025n.
  • Park NY, Kim S, Jung W, Kho Y. 2018. Analysis of nitrosamines concentration in condom by using LC-MS/MS. J Korean Chem Soc. 62(3):181–186.
  • Park JE, Seo JE, Lee JY, Kwon H. 2015. Distribution of seven N-nitrosamines in food. Toxicol Res. 31(3):279–288. doi: 10.5487/TR.2015.31.3.279.
  • Poupin P, Truffaut N, Combourieu B, Besse P, Sancelme M, Veschambre H, Delort AM. 1998. Degradation of morpholine by an environmental Mycobacterium strain involves a cytochrome P-450. Appl Environ Microbiol. 64(1):159–165. doi: 10.1128/AEM.64.1.159-165.1998.
  • Pietsch J, Sacher F, Schmidt W, Brauch H-J. 2001. Polar nitrogen compounds and their behaviour in the drinking water treatment process. Water Res. 35(15):3537–3544. doi: 10.1016/s0043-1354(01)00086-0.
  • Qiu Y, Chen J-H, Yu W, Wang P, Rong M, Deng H. 2017. Contamination of Chinese salted fish with volatile N-nitrosamines as determined by QuEChERS and gas chromatography-tandem mass spectrometry. Food Chem. 232:763–769. doi: 10.1016/j.foodchem.2017.04.055.
  • Rostkowska K, Zwierz K, Różański A, Moniuszko-Jakoniuk J, Roszczenko A. 1988. Formation and metabolism of N-nitrosamines. Pol J Environ Stud. 7(6):321–325.
  • Sluggett GW, Zelesky T, Hetrick EM, Babayan Y, Baertschi SW. 2018. Artifactual degradation of secondary amine-containing drugs during accelerated stability testing when saturated sodium nitrite solutions are used for humidity control. J Pharm Biomed Anal. 149:206–213. doi: 10.1016/j.jpba.2017.10.035.
  • Sohn OS, Fiala ES, Conaway CC, Weisburger JH. 1982. Metabolism and disposition of morpholine in the rat, hamster, and guinea pig. Toxicol Appl Pharmacol. 64(3):486–491. doi: 10.1016/0041-008x(82)90246-0.
  • Tannenbaum SR, Archer MC, Wishnok JS, Bishop WW. 1978. Nitrosamine formation in human saliva. J Natl Cancer Inst. 60(2):251–253. doi: 10.1093/jnci/60.2.251.
  • Tricker AR. 1997. N-nitroso compounds and man: sources of exposure, endogenous formation and occurrence in body fluids. Eur J Cancer Prev. 6(3):226–268. doi: 10.1097/00008469-199706000-00003.
  • Winter JW, Paterson S, Scobie G, Wirz A, Preston T, McColl KEL. 2007. N-nitrosamine generation from ingested nitrate via nitric oxide in subjects with and without gastroesophageal reflux. Gastroenterology. 133(1):164–174. doi: 10.1053/j.gastro.2007.04.047.
  • World Health Organization & International Programme on Chemical Safety. 1995. Morpholine: health and safety guide. World Health Organization. https://apps.who.int/iris/handle/10665/36899.
  • WHO. 2017. Guidelines for drinking-water quality: 4th ed. Incorporating first addendum.
  • Jakszyn P, González CA. 2006. Nitrosamine and related food intake and gastric and oesophageal cancer risk: a systematic review of the epidemiological evidence. World J Gastroenterol. 12(27):4296–4303. doi: 10.3748/wjg.v12.i27.4296.
  • Wang W, Ren S, Zhang H, Yu J, An W, Hu J, Yang M. 2011. Occurrence of nine nitrosamines and secondary amines in source water and drinking water: potential of secondary amines as nitrosamine precursors. Water Res. 45 (16):4930–4938. doi: 10.1016/j.watres.2011.06.041.
  • Zhao B, Wong Y, Ihara M, Nakada N, Yu Z, Sugie Y, Miao J, Tanaka H, Guan Y. 2022. Characterization of nitrosamines and nitrosamine precursors as non-point source pollutants during heavy rainfall events in an urban water environment. J Hazard Mater. 424 (Pt C):127552. doi: 10.1016/j.jhazmat.2021.127552.
  • Zeng T, Mitch W. 2015. Contribution of N-nitrosamines and their precursors to domestic sewage by greywaters and blackwaters. Environ Sci Technol. 49(22):13158–13167. doi: 10.1021/acs.est.5b04254.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.