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Chemical Compound Review

CYCLOHEXYLAMINE     cyclohexanamine

Synonyms: Cyclohexylamin, SureCN2459, AGN-PC-0CYPLH, HSDB 918, ACMC-1BUGG, ...
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Disease relevance of CYCLOHEXYLAMINE

  • This review of the published and unpublished literature on cyclamate attempts to evaluate the carcinogenicity question and other important aspects of the toxicity of cyclamate and cyclohexylamine, including their effects on various organ systems, their genotoxic potential, and their effects on reproduction [1].
  • Biodegradation of cyclohexylamine by Brevibacterium oxydans IH-35A [2].
  • Male Wistar strain rats were fed a diet providing an intake of 0 or 400 mg cyclohexylamine (CHA)/kg body weight/day for 1, 3, 7, 9, or 13 weeks [3].
  • Purification and some properties of cyclohexylamine oxidase from a Pseudomonas sp [4].
  • No evidence was found of a significant association between cyclamate intake and male infertility; neither high cyclamate nor high cyclohexylamine excretion were associated with elevated risk [5].

High impact information on CYCLOHEXYLAMINE


Chemical compound and disease context of CYCLOHEXYLAMINE

  • We have shown that the introduction of amino acid moieties and the replacement of cyclohexylamine with nitroxyl moiety leads to a faster decomposition, higher alkylating, lower carbamoylating activity, better antimelanomic activity and lower general toxicity, when compared to those of CCNU [11].
  • Long term toxicity and reproduction study (including a teratogenicity study) with cyclamate, saccharin and cyclohexylamine [12].

Biological context of CYCLOHEXYLAMINE


Anatomical context of CYCLOHEXYLAMINE


Associations of CYCLOHEXYLAMINE with other chemical compounds



  • These results suggest that cyclohexylamine specifically interacts with the binding of CD23 and IgE [24].
  • The concentrations of cyclohexylamine in the plasma and testes of rats, but not mice, showed a nonlinear relationship to dietary intake [14].
  • 2-Cyclohexylamino-2-demethoxy-hypocrellin B (CHAHB) is a new photosensitizer synthesized by the mild reaction between hypocrellin B (HB) and cyclohexylamine, in which the peri-hydroxylated perylenequinone structure of the parent HB is preserved and the photoresponse is enhanced markedly [25].
  • However, addition of a spermidine synthase inhibitor, cyclohexylamine, at 150 or 250 microg per plant (each dose was applied two times in total at an interval of 4 days) significantly reduced flower primordium counts, indicating that spermidine is involved in floral initiation and floral development in P. tuberosa [26].
  • By using 13C MAS NMR it was shown that the occluded template (cyclohexylamine) is present as ions [27].

Analytical, diagnostic and therapeutic context of CYCLOHEXYLAMINE

  • Since that time, the carcinogenic potential of cyclamate and cyclohexylamine, its principal metabolite, has been reevaluated in a group of well-controlled, well-designed bioassays that have failed to substantiate the earlier findings [1].
  • JM216 (bis-acetato ammine dichloro cyclohexylamine Pt IV) is an oral platinum complex presently undergoing phase II clinical trials [28].
  • The metabolism of cyclamate to cyclohexylamine and its cardiovascular consequences in human volunteers [13].
  • After 7 and 13 weeks testicular atrophy was demonstrated in both strains of rats given cyclohexylamine diet by a decrease in organ weight and by histological changes [29].
  • An HPLC isocratic method with pre-column derivatization and UV detection for the quantification of cyclamate and cyclohexylamine in urine samples is described [20].


  1. Toxicological aspects of cyclamate and cyclohexylamine. Bopp, B.A., Sonders, R.C., Kesterson, J.W. Crit. Rev. Toxicol. (1986) [Pubmed]
  2. Biodegradation of cyclohexylamine by Brevibacterium oxydans IH-35A. Iwaki, H., Shimizu, M., Tokuyama, T., Hasegawa, Y. Appl. Environ. Microbiol. (1999) [Pubmed]
  3. The morphogenesis of cyclohexylamine-induced testicular atrophy in the rat: in vivo and in vitro studies. Creasy, D.M., Ford, G.R., Gray, T.J. Exp. Mol. Pathol. (1990) [Pubmed]
  4. Purification and some properties of cyclohexylamine oxidase from a Pseudomonas sp. Tokieda, T., Niimura, T., Takamura, F., Yamaha, T. J. Biochem. (1977) [Pubmed]
  5. Cyclamate intake and cyclohexylamine excretion are not related to male fertility in humans. Serra-Majem, L., Bassas, L., García-Glosas, R., Ribas, L., Inglés, C., Casals, I., Saavedra, P., Renwick, A.G. Food additives and contaminants. (2003) [Pubmed]
  6. Structure-based design and synthesis of high affinity tripeptide ligands of the Grb2-SH2 domain. Furet, P., Gay, B., Caravatti, G., García-Echeverría, C., Rahuel, J., Schoepfer, J., Fretz, H. J. Med. Chem. (1998) [Pubmed]
  7. Practical cobalt carbonyl catalysis in the thermal Pauson--Khand reaction: efficiency enhancement using Lewis bases. Krafft, M.E., Boñaga, L.V., Hirosawa, C. J. Org. Chem. (2001) [Pubmed]
  8. Biochemical studies of six nitrogen-containing heterocycles in rat tissues. Kitchin, K.T., Brown, J.L., Lijinsky, W. Biochem. Pharmacol. (1989) [Pubmed]
  9. Oxidative deamination of cyclohexylamine and its homologs by rabbit liver microsomes. Kurebayashi, H., Tanaka, A., Yamaha, T. Biochem. Pharmacol. (1979) [Pubmed]
  10. Polyamines inhibit apoptosis in porcine parthenotes developing in vitro. Cui, X.S., Kim, N.H. Mol. Reprod. Dev. (2005) [Pubmed]
  11. Spin labelled nitrosoureas and triazenes and their non-labelled clinically used analogues--a comparative study on their physicochemical properties and antimelanomic effects. Zheleva, A.M., Gadjeva, V.G. International journal of pharmaceutics. (2001) [Pubmed]
  12. Long term toxicity and reproduction study (including a teratogenicity study) with cyclamate, saccharin and cyclohexylamine. Kroes, R., Peters, P.W., Berkvens, J.M., Verschuuren, H.G., de Vries, T., van Esch, G.J. Toxicology (1977) [Pubmed]
  13. The metabolism of cyclamate to cyclohexylamine and its cardiovascular consequences in human volunteers. Buss, N.E., Renwick, A.G., Donaldson, K.M., George, C.F. Toxicol. Appl. Pharmacol. (1992) [Pubmed]
  14. The pharmacokinetics and tissue concentrations of cyclohexylamine in rats and mice. Roberts, A., Renwick, A.G. Toxicol. Appl. Pharmacol. (1989) [Pubmed]
  15. Assessment of the genotoxicity of calcium cyclamate and cyclohexylamine. Brusick, D., Cifone, M., Young, R., Benson, S. Environ. Mol. Mutagen. (1989) [Pubmed]
  16. Evaluation of the mutagenic potential of cyclohexylamine on spermatogonia of the Chinese hamster. Machemer, L., Lorke, D. Mutat. Res. (1976) [Pubmed]
  17. The present lack of evidence for unique rodent germ-cell mutagens. Adler, I.D., Ashby, J. Mutat. Res. (1989) [Pubmed]
  18. Studies of saccharin and cyclohexylamine in a coupled microsomal activating/embryo culture system. Kitchin, K.T., Ebron, M.T. Food Chem. Toxicol. (1983) [Pubmed]
  19. Cyclohexylamine inhibits the adhesion of lymphocytic cells to human syncytiotrophoblast. Douglas, G.C., Hu, J., Thirkill, T.L., Hovanes, K., Fuller, M., King, B.F. Biochim. Biophys. Acta (1995) [Pubmed]
  20. Quantification of cyclamate and cyclohexylamine in urine samples using high-performance liquid chromatography with trinitrobenzenesulfonic acid pre-column derivatization. Casals, I., Reixach, M., Amat, J., Fuentes, M., Serra-Majem, L. Journal of chromatography. A. (1996) [Pubmed]
  21. Kinetics of tissue disposition of cis-ammine/cyclohexylamine-dichloroplatinum(II) and cisplatin in mice bearing FSaIIC tumors. Yoshida, M., Khokhar, A.R., Zhang, Y.P., Thai, G., Siddik, Z.H. Cancer Chemother. Pharmacol. (1994) [Pubmed]
  22. Enzyme inhibition during the conversion of squalene to cholesterol. Lewis, D., Galczenski, H., Needle, S., Tang, S.Y., Amin, D., Gleason, M., Bilder, G., Perrone, M., Merkel, L., Rojas, C. Steroids (1995) [Pubmed]
  23. [3H]GABA uptake as a marker for cell type in primary cultures of cerebellum and olfactory bulb. Currie, D.N., Dutton, G.R. Brain Res. (1980) [Pubmed]
  24. A new method for studying the binding of human IgE to CD23 and the inhibition of this binding. Sato, T., Konishi, A., Yasuno, S., Arai, J., Kamei, M., Bitoh, M., Yamaguchi, T. J. Immunol. Methods (1997) [Pubmed]
  25. Cyclohexylamino-demethoxy-hypocrellin B and photodynamic therapy decreases human cancer in vitro. Xu, S., Chen, S., Zhang, M., Shen, T., Liu, Z., Zhao, Y., Wu, Y. Anticancer Drug Des. (2001) [Pubmed]
  26. Changes in polyamine pattern are involved in floral initiation and development in Polianthes tuberosa. Huang, C.K., Chang, B.S., Wang, K.C., Her, S.J., Chen, T.W., Chen, Y.A., Cho, C.L., Liao, L.J., Huang, K.L., Chen, W.S., Liu, Z.H. J. Plant Physiol. (2004) [Pubmed]
  27. Multinuclear MAS NMR study of the microporous aluminophosphate AlPO4-17 and the related silicoaluminophosphate SAPO-17. Zibrowius, B., Lohse, U. Solid state nuclear magnetic resonance. (1992) [Pubmed]
  28. Intracellular metabolism of the orally active platinum drug JM216: influence of glutathione levels. Raynaud, F.I., Odell, D.E., Kelland, L.R. Br. J. Cancer (1996) [Pubmed]
  29. The metabolism and testicular toxicity of cyclohexylamine in rats and mice during chronic dietary administration. Roberts, A., Renwick, A.G., Ford, G., Creasy, D.M., Gaunt, I. Toxicol. Appl. Pharmacol. (1989) [Pubmed]
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