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Chemical Compound Review

agmatine     2-(4-aminobutyl)guanidine

Synonyms: Argmatine, AmbotzHNN1040, Lopac-A-7127, Tocris-0842, CHEMBL58343, ...
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Disease relevance of agmatine

  • As a result of its ability to inhibit both hyperalgesia and tolerance to, and withdrawal from, morphine, and its neuroprotective activity, agmatine has potential as a treatment of chronic pain, addictive states and brain injury [1].
  • Biosynthesis of polyamines in ornithine decarboxylase, arginine decarboxylase, and agmatine ureohydrolase deletion mutants of Escherichia coli strain K-12 [2].
  • To test this hypothesis, mRt6.1 and rat RT6.2 were synthesized in Sf9 insect cells and rat mammary adenocarcinoma (NMU) cells. mRt6.1, but not rat RT6.2, catalyzed the ADP-ribosylation of guanidino-containing compounds (e.g. agmatine) [3].
  • Homologs of PvlArgDC are found in several bacterial genomes, including those of Chlamydia spp., which have no agmatine ureohydrolase enzyme to convert agmatine (decarboxylated arginine) into putrescine [4].
  • In the extreme thermophile Thermus thermophilus, a disruption mutant of a gene homologous to speB (coding for agmatinase = agmatine ureohydrolase) accumulated N1-aminopropylagmatine (N8-amidino-1,8-diamino-4-azaoctane, N8-amidinospermidine), a new compound, whereas all other polyamines produced by the wild-type strain were absent from the cells [5].

Psychiatry related information on agmatine


High impact information on agmatine

  • Agmatine binds to alpha 2-adrenergic and imidazoline receptors and stimulates release of catecholamines from adrenal chromaffin cells [11].
  • The presence of agmatine and its biosynthetic enzyme in synaptosomes and specific neuronal pathways as well as serum suggests that it may be a novel neurotransmitter/hormone [12].
  • Diamine oxidase, an enzyme shown here to metabolize agmatine, was localized by immunohistochemistry in kidney glomeruli and other nonrenal cells [13].
  • Microperfusion of agmatine into renal interstitium and into the urinary space of surface glomeruli of Wistar-Frömter rats produced reversible increases in nephron filtration rate (SNGFR) and absolute proximal reabsorption (APR) [13].
  • Agmatine binds to alpha2-adrenoceptors and imidazoline binding sites, and blocks NMDA receptor channels and other ligand-gated cationic channels [1].

Chemical compound and disease context of agmatine


Biological context of agmatine


Anatomical context of agmatine


Associations of agmatine with other chemical compounds


Gene context of agmatine

  • A strong correlation was observed between the effects of LPS on the agmatine-related enzymes and iNOS [28].
  • Consequently, agmatine affects selection between the monocistronic and the polycistronic modes of speB transcription [29].
  • Uptake of agmatine via EMT and OCT2 was saturable, with K(m) values of 1 to 2 mM [30].
  • In conclusion, both EMT and OCT2 must be considered for the control of agmatine levels in rat and human [30].
  • This loss of mitogenic response in cells expressing ART1 activity was reversed by the addition of agmatine (an ART1 substrate) [31].

Analytical, diagnostic and therapeutic context of agmatine


  1. Is agmatine a novel neurotransmitter in brain? Reis, D.J., Regunathan, S. Trends Pharmacol. Sci. (2000) [Pubmed]
  2. Biosynthesis of polyamines in ornithine decarboxylase, arginine decarboxylase, and agmatine ureohydrolase deletion mutants of Escherichia coli strain K-12. Panagiotidis, C.A., Blackburn, S., Low, K.B., Canellakis, E.S. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  3. Characterization of mouse Rt6.1 NAD:arginine ADP-ribosyltransferase. Moss, J., Stevens, L.A., Cavanaugh, E., Okazaki, I.J., Bortell, R., Kanaitsuka, T., Mordes, J.P., Greiner, D.L., Rossini, A.A. J. Biol. Chem. (1997) [Pubmed]
  4. Methanococcus jannaschii uses a pyruvoyl-dependent arginine decarboxylase in polyamine biosynthesis. Graham, D.E., Xu, H., White, R.H. J. Biol. Chem. (2002) [Pubmed]
  5. N1-aminopropylagmatine, a new polyamine produced as a key intermediate in polyamine biosynthesis of an extreme thermophile, Thermus thermophilus. Ohnuma, M., Terui, Y., Tamakoshi, M., Mitome, H., Niitsu, M., Samejima, K., Kawashima, E., Oshima, T. J. Biol. Chem. (2005) [Pubmed]
  6. IRAS, a candidate for I1-imidazoline receptor, mediates inhibitory effect of agmatine on cellular morphine dependence. Wu, N., Su, R.B., Xu, B., Lu, X.Q., Liu, Y., Zheng, J.Q., Piletz, J.E., Li, J., Qin, B.Y. Biochem. Pharmacol. (2005) [Pubmed]
  7. Effect of intrathecal agmatine on inflammation-induced thermal hyperalgesia in rats. Horváth, G., Kékesi, G., Dobos, I., Szikszay, M., Klimscha, W., Benedek, G. Eur. J. Pharmacol. (1999) [Pubmed]
  8. Agmatine and a cannabinoid agonist, WIN 55212-2, interact to produce a hypothermic synergy. Rawls, S.M., Tallarida, R.J., Zisk, J. Eur. J. Pharmacol. (2006) [Pubmed]
  9. Effects of agmatine on ethanol withdrawal syndrome in rats. Uzbay, I.T., Yeşilyurt, O., Celik, T., Ergün, H., Işimer, A. Behav. Brain Res. (2000) [Pubmed]
  10. Anxiolytic effect of agmatine in rats and mice. Gong, Z.H., Li, Y.F., Zhao, N., Yang, H.J., Su, R.B., Luo, Z.P., Li, J. Eur. J. Pharmacol. (2006) [Pubmed]
  11. Agmatine: an endogenous clonidine-displacing substance in the brain. Li, G., Regunathan, S., Barrow, C.J., Eshraghi, J., Cooper, R., Reis, D.J. Science (1994) [Pubmed]
  12. Imidazoline receptors and their endogenous ligands. Regunathan, S., Reis, D.J. Annu. Rev. Pharmacol. Toxicol. (1996) [Pubmed]
  13. Agmatine, a bioactive metabolite of arginine. Production, degradation, and functional effects in the kidney of the rat. Lortie, M.J., Novotny, W.F., Peterson, O.W., Vallon, V., Malvey, K., Mendonca, M., Satriano, J., Insel, P., Thomson, S.C., Blantz, R.C. J. Clin. Invest. (1996) [Pubmed]
  14. Agmatine transport into spinal nerve terminals is modulated by polyamine analogs. Goracke-Postle, C.J., Overland, A.C., Stone, L.S., Fairbanks, C.A. J. Neurochem. (2007) [Pubmed]
  15. Suppression of inducible nitric oxide generation by agmatine aldehyde: beneficial effects in sepsis. Satriano, J., Schwartz, D., Ishizuka, S., Lortie, M.J., Thomson, S.C., Gabbai, F., Kelly, C.J., Blantz, R.C. J. Cell. Physiol. (2001) [Pubmed]
  16. Metabolic pathway for the utilization of L-arginine, L-ornithine, agmatine, and putrescine as nitrogen sources in Escherichia coli K-12. Shaibe, E., Metzer, E., Halpern, Y.S. J. Bacteriol. (1985) [Pubmed]
  17. Central cardiovascular actions of agmatine, a putative clonidine-displacing substance, in conscious rabbits. Head, G.A., Chan, C.K., Godwin, S.J. Neurochem. Int. (1997) [Pubmed]
  18. Molecular characterization and regulation of the aguBA operon, responsible for agmatine utilization in Pseudomonas aeruginosa PAO1. Nakada, Y., Jiang, Y., Nishijyo, T., Itoh, Y., Lu, C.D. J. Bacteriol. (2001) [Pubmed]
  19. Ifosfamide-induced nephrotoxicity: mechanism and prevention. Nissim, I., Horyn, O., Daikhin, Y., Nissim, I., Luhovyy, B., Phillips, P.C., Yudkoff, M. Cancer Res. (2006) [Pubmed]
  20. Agmatine suppresses proliferation by frameshift induction of antizyme and attenuation of cellular polyamine levels. Satriano, J., Matsufuji, S., Murakami, Y., Lortie, M.J., Schwartz, D., Kelly, C.J., Hayashi, S., Blantz, R.C. J. Biol. Chem. (1998) [Pubmed]
  21. A bacterial arginine-agmatine exchange transporter involved in extreme Acid resistance. Fang, Y., Kolmakova-Partensky, L., Miller, C. J. Biol. Chem. (2007) [Pubmed]
  22. Agmatine stimulates hepatic fatty acid oxidation: a possible mechanism for up-regulation of ureagenesis. Nissim, I., Daikhin, Y., Nissim, I., Luhovyy, B., Horyn, O., Wehrli, S.L., Yudkoff, M. J. Biol. Chem. (2006) [Pubmed]
  23. Agmatine reverses pain induced by inflammation, neuropathy, and spinal cord injury. Fairbanks, C.A., Schreiber, K.L., Brewer, K.L., Yu, C.G., Stone, L.S., Kitto, K.F., Nguyen, H.O., Grocholski, B.M., Shoeman, D.W., Kehl, L.J., Regunathan, S., Reis, D.J., Yezierski, R.P., Wilcox, G.L. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  24. Agmatine inhibits cell proliferation and improves renal function in anti-thy-1 glomerulonephritis. Ishizuka, S., Cunard, R., Poucell-Hatton, S., Wead, L., Lortie, M., Thomson, S.C., Gabbai, F.B., Satriano, J., Blantz, R.C. J. Am. Soc. Nephrol. (2000) [Pubmed]
  25. Activation of imidazoline receptors in adrenal gland to lower plasma glucose in streptozotocin-induced diabetic rats. Hwang, S.L., Liu, I.M., Tzeng, T.F., Cheng, J.T. Diabetologia (2005) [Pubmed]
  26. Enhancement of choleragen ADP-ribosyltransferase activities by guanyl nucleotides and a 19-kDa membrane protein. Tsai, S.C., Noda, M., Adamik, R., Moss, J., Vaughan, M. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  27. Regulation of arginine metabolism in Saccharomyces cerevisiae. Association of arginase and ornithine transcarbamoylase. Eisenstein, E., Duong, L.T., Ornberg, R.L., Osborne, J.C., Hensley, P. J. Biol. Chem. (1986) [Pubmed]
  28. Metabolism of agmatine in macrophages: modulation by lipopolysaccharide and inhibitory cytokines. Sastre, M., Galea, E., Feinstein, D., Reis, D.J., Regunathan, S. Biochem. J. (1998) [Pubmed]
  29. Influence of cyclic AMP, agmatine, and a novel protein encoded by a flanking gene on speB (agmatine ureohydrolase) in Escherichia coli. Szumanski, M.B., Boyle, S.M. J. Bacteriol. (1992) [Pubmed]
  30. Agmatine is efficiently transported by non-neuronal monoamine transporters extraneuronal monoamine transporter (EMT) and organic cation transporter 2 (OCT2). Gründemann, D., Hahne, C., Berkels, R., Schömig, E. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  31. Inactivation of platelet-derived growth factor-BB following modification by ADP-ribosyltransferase. Saxty, B.A., Yadollahi-Farsani, M., Upton, P.D., Johnstone, S.R., MacDermot, J. Br. J. Pharmacol. (2001) [Pubmed]
  32. Improved method for HPLC analysis of polyamines, agmatine and aromatic monoamines in plant tissue. Slocum, R.D., Flores, H.E., Galston, A.W., Weinstein, L.H. Plant Physiol. (1989) [Pubmed]
  33. Agmatine potentiates the analgesic effect of morphine by an alpha(2)-adrenoceptor-mediated mechanism in mice. Yeşilyurt, O., Uzbay, I.T. Neuropsychopharmacology (2001) [Pubmed]
  34. Agmatine inhibits the proliferation of rat hepatoma cells by modulation of polyamine metabolism. Gardini, G., Cravanzola, C., Autelli, R., Testore, G., Cesa, R., Morando, L., Solinas, S.P., Muzio, G., Grillo, M.A., Colombatto, S. J. Hepatol. (2003) [Pubmed]
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