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Chemical Compound Review

Propanamine     propan-1-amine

Synonyms: Propylamine, n-Propylamine, n-Propyl Amine, CHEMBL14409, NSC-7490, ...
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Disease relevance of propyl amines


Psychiatry related information on propyl amines

  • The response time (t (100)) for the base-catalyzed sensor layer L3 (pH 13) upon exposure to different solutions containing 0-608 mmol L(-1) aqueous propylamine was 20-30 s, the regeneration time was 70 s and the detection limit was 0.1 mmol L(-1) [6].

High impact information on propyl amines

  • It is reasoned that perturbation of a second regulatory element in polyamine biosynthesis, i.e., the generation of propylamine groups from S-adenosylmethionine (AdoMet), would potentiate the effectiveness of DFMO [7].
  • Therefore, we used a proteomic approach using selective peptide capturing and site-specific adduct mapping to identify the targets of S-nitrosylation in human aortic smooth muscle cells upon exposure to S-nitrosocysteine and propylamine propylamine NONOate [8].
  • Appreciable amounts of nitrotyrosine were produced by ONOO(-) formed in situ (2.9 micrometer for 5 min; 10 nm/s) by NO/O(2) flux obtained from propylamine NONOate (CH(3)N[N(O)NO](-) (CH(2))(3)NH(2)(+)CH(3)) and xanthine oxidase using pterin as a substrate in phosphate buffer (pH 7.0) containing 0.1 mm l-tyrosine [9].
  • S-Adenosylmethionine serves as the methyl donor for many biological methylation reactions and provides the propylamine group for the synthesis of polyamines [10].
  • In summary, these data show the presence of two distinct amadoriase enzymes in the Aspergillus sp. soil strain selected on fructosyl adamantanamine and induced by fructosyl propylamine [11].

Chemical compound and disease context of propyl amines


Biological context of propyl amines


Anatomical context of propyl amines

  • Compound 24, a propylamine analogue with potency and efficacy comparable to those of UK-68798 (2) and E-4031 (3), was studied in voltage-clamp experiments (isolated cat myocytes) and was found to be a potent and specific blocker of the delayed rectifier potassium current (IK) [18].
  • IRS decreasing activity in gastric mucosa, expressed as percentage of controls is listed in descending order: cystamine (55%), cysteamine (59%), 2-dimethylaminethanethiol (59%), ethylamine (66%), 1,3-propanedithiol (70%), propylamine (75%) and 3-aminothiophenol (79%) [19].
  • Glass coverslips were coated with 3-aminopropyl triethoxysilane and glutaraldehyde to make erythrocytes stick to them [20].
  • Immersion of the nascent axon tips in solutions containing 10 mM ammonium choloride or 10 mM propylamine caused the axon tips to become distended by an accumulation of elongated membranous tubules and occasional large vacuoles that were both distinct from retrograde organelles [21].
  • Normal human fibroblasts were exposed to NO produced by the rapid decomposition of 1-propanamine, 3-(2-hydroxy-2-nitroso-1-propylhydrazino) (PAPA NONOate) and the resultant damage to mtDNA was determined by quantitative Southern blot analysis [22].

Associations of propyl amines with other chemical compounds


Gene context of propyl amines

  • The ability of the Tyr-293-->Ile mutated GLUT1 to bind the exofacial ligand 2-N-4-(1-azi-2,2,2-trifluoroethyl)benzoyl-1,3-bis-(D-mannos- 4-yloxy)-2- propylamine (ATB-BMPA) and the endofacial ligand cytochalasin B were assessed by photolabeling procedures [28].
  • 1. The specificity of rat prostatic spermidine synthase and spermine synthase with respect to the amine acceptor of the propylamine group was studied [29].
  • This modified version of the DDD, called here the DDD(4+), is composed of [d(CGCGAAXXCGCG)](2), where X is effectively a thymine residue linked at the 5 position to an n-propyl-amine [30].
  • OBJECT: The authors sought to determine whether 3,3-bis (3-fluorophenyl) propylamine (NPS 846), a novel noncompetitive N-methyl-D-aspartate receptor antagonist, alters outcome after closed head trauma in rats [31].
  • Water-soluble T-antigen containing glycopolymers [Gal beta(1,3)-GalNAc alpha) having a high degree of lipophilicity were synthesized from poly[N-(acryloxy)succinimide] (6-10) by amidation with an amine-ending T-antigen derivative (3) and various amines of increasing alkyl chain length (ammonia and methyl-, ethyl-, and propylamine) [32].

Analytical, diagnostic and therapeutic context of propyl amines


  1. Mechanism of propylamine-transfer reactions. Kinetic and inhibition studies on spermidine synthase from Escherichia coli. Zappia, V., Cacciapuoti, G., Pontoni, G., Oliva, A. J. Biol. Chem. (1980) [Pubmed]
  2. Metabolism of n-propylamine, isopropylamine, and 1,3-propane diamine by Mycobacterium convolutum. Cerniglia, C.E., Perry, J.J. J. Bacteriol. (1975) [Pubmed]
  3. Simple mimetics of a nuclear localization signal (NLS). Park, S.B., Ho, T.H., Reedy, B.M., Connolly, M.D., Standaert, R.F. Org. Lett. (2003) [Pubmed]
  4. Influence of pH, nutrient availability, and growth rate on amine production by Bacteroides fragilis and Clostridium perfringens. Allison, C., Macfarlane, G.T. Appl. Environ. Microbiol. (1989) [Pubmed]
  5. Induction of non-specific suppressor cells in normal Lewis rats by a novel azaspirane SK&F 105685. Badger, A.M., King, A.G., Talmadge, J.E., Schwartz, D.A., Picker, D.H., Mirabelli, C.K., Hanna, N. J. Autoimmun. (1990) [Pubmed]
  6. Sol-gel-based optical sensor for the detection of aqueous amines. Korent, S.M., Lobnik, A., Mohr, G.J. Analytical and bioanalytical chemistry (2007) [Pubmed]
  7. New approaches to cancer chemoprevention with difluoromethylornithine and selenite. Ip, C., Thompson, H.J. J. Natl. Cancer Inst. (1989) [Pubmed]
  8. Identification of S-nitrosylation motifs by site-specific mapping of the S-nitrosocysteine proteome in human vascular smooth muscle cells. Greco, T.M., Hodara, R., Parastatidis, I., Heijnen, H.F., Dennehy, M.K., Liebler, D.C., Ischiropoulos, H. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  9. Tyrosine nitration by peroxynitrite formed from nitric oxide and superoxide generated by xanthine oxidase. Sawa, T., Akaike, T., Maeda, H. J. Biol. Chem. (2000) [Pubmed]
  10. Methionine adenosyltransferase S-nitrosylation is regulated by the basic and acidic amino acids surrounding the target thiol. Pérez-Mato, I., Castro, C., Ruiz, F.A., Corrales, F.J., Mato, J.M. J. Biol. Chem. (1999) [Pubmed]
  11. Isolation, purification, and characterization of amadoriase isoenzymes (fructosyl amine-oxygen oxidoreductase EC 1.5.3) from Aspergillus sp. Takahashi, M., Pischetsrieder, M., Monnier, V.M. J. Biol. Chem. (1997) [Pubmed]
  12. Inducement of respiratory mucosal immunogenicity for nasal vaccine due to amine- and amide-inactivation of parainfluenza virus type 1, Sendai. Miyamae, T. Microbiol. Immunol. (1994) [Pubmed]
  13. Energy dependence of different steps in the autophagic-lysosomal pathway. Plomp, P.J., Gordon, P.B., Meijer, A.J., Høyvik, H., Seglen, P.O. J. Biol. Chem. (1989) [Pubmed]
  14. Molecular cloning and expression of amadoriase isoenzyme (fructosyl amine:oxygen oxidoreductase, EC 1.5.3) from Aspergillus fumigatus. Takahashi, M., Pischetsrieder, M., Monnier, V.M. J. Biol. Chem. (1997) [Pubmed]
  15. Comprehensive analysis of the substituent distribution in the glucosyl units and along the polymer chain of hydroxyethylmethyl celluloses and statistical evaluation. Adden, R., Niedner, W., Müller, R., Mischnick, P. Anal. Chem. (2006) [Pubmed]
  16. Role of cytochrome P450 in DNA damage induced by N-nitrosodialkylamines in cultured rat hepatocytes. Shu, L., Hollenberg, P.F. Carcinogenesis (1996) [Pubmed]
  17. Transgenic mice overexpressing ornithine and S-adenosylmethionine decarboxylases maintain a physiological polyamine homoeostasis in their tissues. Heljasvaara, R., Veress, I., Halmekytö, M., Alhonen, L., Jänne, J., Laajala, P., Pajunen, A. Biochem. J. (1997) [Pubmed]
  18. Synthesis and selective class III antiarrhythmic activity of novel N-heteroaralkyl-substituted 1-(aryloxy)-2-propanolamine and related propylamine derivatives. Butera, J.A., Spinelli, W., Anantharaman, V., Marcopulos, N., Parsons, R.W., Moubarak, I.F., Cullinan, C., Bagli, J.F. J. Med. Chem. (1991) [Pubmed]
  19. 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]
  20. An ultrastructural study of the cytoplasmic aspects of erythrocyte membranes by a quick-freezing and deep-etching method. Ohno, S. J. Anat. (1992) [Pubmed]
  21. Weak-base amines inhibit the anterograde-to-retrograde conversion of axonally transported vesicles in nerve terminals. Sahenk, Z., Brown, A. J. Neurocytol. (1991) [Pubmed]
  22. Nitric oxide-induced damage to mtDNA and its subsequent repair. Grishko, V.I., Druzhyna, N., LeDoux, S.P., Wilson, G.L. Nucleic Acids Res. (1999) [Pubmed]
  23. Degradation of short and long lived proteins in isolated rat liver lysosomes. Effects of pH, temperature, and proteolytic inhibitors. Ahlberg, J., Berkenstam, A., Henell, F., Glaumann, H. J. Biol. Chem. (1985) [Pubmed]
  24. Peroxynitrite modulates MnSOD gene expression in lung epithelial cells. Jackson, R.M., Parish, G., Helton, E.S. Free Radic. Biol. Med. (1998) [Pubmed]
  25. The inhibition of glucose-stimulated insulin secretion by primary amines. A role for transglutaminase in the secretory mechanism. Bungay, P.J., Potter, J.M., Griffin, M. Biochem. J. (1984) [Pubmed]
  26. Optical sensor for amine vapors based on dimer-monomer equilibrium of indium(III) octaethylporphyrin in a polymeric film. Qin, W., Parzuchowski, P., Zhang, W., Meyerhoff, M.E. Anal. Chem. (2003) [Pubmed]
  27. Polyamine synthesis in mammalian tissues. Isolation and characterization of spermidine synthase from bovine brain. Raina, A., Hyvönen, T., Eloranta, T., Voutilainen, M., Samejima, K., Yamanoha, B. Biochem. J. (1984) [Pubmed]
  28. Substitution of tyrosine 293 of GLUT1 locks the transporter into an outward facing conformation. Mori, H., Hashiramoto, M., Clark, A.E., Yang, J., Muraoka, A., Tamori, Y., Kasuga, M., Holman, G.D. J. Biol. Chem. (1994) [Pubmed]
  29. Specificity of mammalian spermidine synthase and spermine synthase. Pegg, A.E., Shuttleworth, K., Hibasami, H. Biochem. J. (1981) [Pubmed]
  30. Structure of B-DNA with cations tethered in the major groove. Moulaei, T., Maehigashi, T., Lountos, G.T., Komeda, S., Watkins, D., Stone, M.P., Marky, L.A., Li, J.S., Gold, B., Williams, L.D. Biochemistry (2005) [Pubmed]
  31. Neuroprotective effects of NPS 846, a novel N-methyl-D-aspartate receptor antagonist, after closed head trauma in rats. Gurevich, B., Artru, A.A., Lam, A.M., Mueller, A.L., Merkind, V., Talmor, D., Katchko, L., Shapira, Y. J. Neurosurg. (1998) [Pubmed]
  32. Design and synthesis of water-soluble glycopolymers bearing breast tumor marker and enhanced lipophilicity for solid-phase assays. Baek, M.G., Roy, R. Biomacromolecules (2000) [Pubmed]
  33. Analysis of mucin-derived oligosaccharides by medium-pressure gel-permeation and amino-plate thin-layer chromatography conducted in conjunction. Goso, Y., Hotta, K. Anal. Biochem. (1990) [Pubmed]
  34. Polymeric reagents for derivatizations in micellar electrokinetic chromatography. Szulc, M., Krull, I.S. Biomed. Chromatogr. (1994) [Pubmed]
  35. Frontal type dementia preceding amyotrophic lateral sclerosis: a neuropsychological and SPECT study of five clinical cases. Vercelletto, M., Ronin, M., Huvet, M., Magne, C., Feve, J.R. Eur. J. Neurol. (1999) [Pubmed]
  36. Identification of ejaculate derived propylamine found in collagen sponge contraceptives. Eskelson, C.D., Chvapil, M., Chang, S.Y., Chvapil, T. Biomed. Mass Spectrom. (1978) [Pubmed]
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