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Chemical Compound Review

m-Aminofenol     3-aminophenol

Synonyms: M-AMINOPHENOL, AMINOPHENOL-3, Fouramine EG, Futramine EG, Fourrine 65, ...
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Disease relevance of UN2512


High impact information on UN2512

  • 4-HC was measured in cerebrospinal fluid (CSF) and plasma with a high-performance liquid chromatography assay utilizing a fluorometric detector following derivatization with m-aminophenol [6].
  • The rate of oxidation of 2-amino-6-nitrobenzyl alcohol was lower with microsomes from female rats than with those from males, yielding male/female ratios of 1.34 for aminophenol formation and 3.26 for hydroxylamine formation [7].
  • To test the robustness of the resulting QSAR model, the synthesis of a series of non-peptide thrombin inhibitors based on arylsuphonyl derivatives of an aminophenol ring linked to a pyridyl-based S1 binding group was undertaken [8].
  • Genetic and structural organization of the aminophenol catabolic operon and its implication for evolutionary process [1].
  • The aryl 2-, 3- or 4-aminothiophenols, unlike most of their aminophenol analogs also decreased immunoreactive prolactin in the pituitary by 38 to 78% [9].

Chemical compound and disease context of UN2512


Biological context of UN2512


Anatomical context of UN2512


Associations of UN2512 with other chemical compounds

  • Finally, a pattern was observed in which C. neoformans produced large amounts of pigment from aminophenol and diaminobenzene compounds, whereas the other Cryptococcus species produced smaller amounts [15].
  • The ready and quantitative transacetylation of 3-aminophenol by aspirin, giving 3-hydroxyacetanilide (which is stable), has been utilized as a pre-column reaction for the determination of aspirin either alone or in the presence of acetaminophen and caffeine by reversed-phase HPLC [16].
  • Succinic acid aminophenol derivatives 1b-e and 2b-d act as reversible inhibitors of acetylcholinesterase, while maleic acid aminophenol derivatives 3b-d and 4c-e act as choline subsite-directed irreversible inhibitors, detected by dialysis in the presence of edrophonium [17].
  • The most efficient inhibitor is ADTBP characterized by K(i) = 36 microM in 0.015 M phosphate citrate buffer, pH 6.0, at 20 degrees C. According to their antiradical efficiency, the studied inhibitors can be arranged as follows: ADTBP > ATBP > AP > TBP [18].

Gene context of UN2512

  • The beta-galactosidase label hydrolyses the substrate aminophenyl-beta-galactopyranoside, and the generated aminophenol enters then into a bioelectrocatalytic amplification cycle at the GDH biosensor [19].
  • Bound antibodies are monitored by following the electro-oxidation of aminophenol, produced enzymatically from p-amino-phenyl phosphate by the immobilized alkaline phosphatase at the electrode surface [20].

Analytical, diagnostic and therapeutic context of UN2512


  1. Genetic and structural organization of the aminophenol catabolic operon and its implication for evolutionary process. Park, H.S., Kim, H.S. J. Bacteriol. (2001) [Pubmed]
  2. Effect of nitrogen limitation on the biodegradability and toxicity of nitro- and aminophenol isomers to methanogenesis. O'Connor, O.A., Young, L.Y. Arch. Environ. Contam. Toxicol. (1993) [Pubmed]
  3. Contact dermatitis to 2-hydroxyethylamino-5-nitroanisole and 3-nitro-p-hydroxyethyl aminophenol in a hair dye. Dejobert, Y., Piette, F., Thomas, P. Contact Derm. (2006) [Pubmed]
  4. Potent anticancer activities of novel aminophenol analogues against various cancer cell lines. Ohba, T., Yamauch, T., Higashiyama, K., Takahashi, N. Bioorg. Med. Chem. (2007) [Pubmed]
  5. Degradation of 3-aminophenol by Arthrobacter spec. mA3. Lechner, U., Straube, G. J. Basic Microbiol. (1988) [Pubmed]
  6. Intrathecal administration of 4-hydroperoxycyclophosphamide in rhesus monkeys. Arndt, C.A., Colvin, O.M., Balis, F.M., Lester, C.M., Johnson, G., Poplack, D.G. Cancer Res. (1987) [Pubmed]
  7. Characterization of the oxidation of amine metabolites of nitrotoluenes by rat hepatic microsomes. N- and C-hydroxylation. Kedderis, G.L., Rickert, D.E. Mol. Pharmacol. (1985) [Pubmed]
  8. Generation of ligand conformations in continuum solvent consistent with protein active site topology: application to thrombin. Greenidge, P.A., Mérette, S.A., Beck, R., Dodson, G., Goodwin, C.A., Scully, M.F., Spencer, J., Weiser, J., Deadman, J.J. J. Med. Chem. (2003) [Pubmed]
  9. Somatostatin depleting potency of cysteamine-related thiols and amines in the rat: structure-activity relation. Szabo, S., Reichlin, S., Bollinger-Gruber, J.A., Brown, A. J. Pharmacol. Exp. Ther. (1992) [Pubmed]
  10. Bioconversion of 1,3 dinitrobenzene by Micrococcus colpogenes strain MCM B410: quantitation and characterization of the intermediates. Dey, S. Journal of environmental biology / Academy of Environmental Biology, India. (2001) [Pubmed]
  11. Enhancement of antioxidant activity of p-alkylaminophenols by alkyl chain elongation. Takahashi, N., Tamagawa, K., Kubo, Y., Fukui, T., Wakabayashi, H., Honda, T. Bioorg. Med. Chem. (2003) [Pubmed]
  12. Comparative toxicity study of 3-aminophenol in newborn and young rats. Koizumi, M., Nishimura, N., Enami, T., Sunaga, M., Horikawa, H., Kamata, E., Hasegawa, R. The Journal of toxicological sciences. (2002) [Pubmed]
  13. Genotoxic activity of the aminophenols as evidenced by the induction of sister chromatid exchanges. Kirchner, G., Bayer, U. Human toxicology. (1982) [Pubmed]
  14. Activation of aniline by extracts from plants and induction of chromosomal damages in Chinese hamster ovary cells. Kanaya, N. Genes Genet. Syst. (1996) [Pubmed]
  15. Pigment production by Cryptococcus neoformans and other Cryptococcus species from aminophenols and diaminobenzenes. Chaskes, S., Tyndall, R.L. J. Clin. Microbiol. (1978) [Pubmed]
  16. Determination of aspirin by pre-column transacetylation reaction of 3-aminophenol and reversed-phase high-performance liquid chromatography: simultaneous determination of aspirin, acetaminophen, and caffeine. Verma, K.K., Sanghi, S.K., Jain, A., Gupta, D. Journal of pharmaceutical sciences. (1987) [Pubmed]
  17. Reversible and irreversible inhibitory activity of succinic and maleic acid derivatives on acetylcholinesterase. Trujillo-Ferrara, J., Vázquez, I., Espinosa, J., Santillan, R., Farfán, N., Höpfl, H. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. (2003) [Pubmed]
  18. Inhibition of peroxidase-catalyzed oxidation of 3,3 ,5,5 -tetramethylbenzidine by aminophenols. Naumchik, I.V., Karasyova, E.I., Metelitza, D.I., Edimecheva, I.P., Sorokin, V.L., Shadyro, O.I. Biochemistry Mosc. (2005) [Pubmed]
  19. A glucose dehydrogenase biosensor as an additional signal amplification step in an enzyme-flow immunoassay. Nistor, C., Rose, A., Wollenberger, U., Pfeiffer, D., Emnéus, J. The Analyst. (2002) [Pubmed]
  20. A rapid and sensitive heterogeneous immunoelectrochemical assay using disposable electrodes. Hadas, E., Soussan, L., Rosen-Margalit, I., Farkash, A., Rishpon, J. Journal of immunoassay. (1992) [Pubmed]
  21. Cerebrospinal fluid penetration of active metabolites of cyclophosphamide and ifosfamide in rhesus monkeys. Arndt, C.A., Balis, F.M., McCully, C.L., Colvin, O.M., Poplack, D.G. Cancer Res. (1988) [Pubmed]
  22. Colorimetry of carbohydrates with m-aminophenol, and its proposed use in measurement of serum amylase activity. Goodwin, J.F. Clin. Chem. (1976) [Pubmed]
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