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Chemical Compound Review

IMAC     2-(3H-imidazol-4-yl)ethanoic acid

Synonyms: SureCN49, CHEMBL784, Lopac-I-0375, zlchem 872, SureCN637983, ...
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Disease relevance of C02835


Psychiatry related information on C02835


High impact information on C02835

  • Complete chemical ionization mass spectra and mass ion abundance ratios established the identity of N tau - and N pi - methylimidazoleacetic acids in the biological extracts and of imidazoleacetic acid in urine, but not in cerebrospinal fluid, plasma, and brain [3].
  • In this study, the kinetics of reaction of His side-chain chloramines with other protein components have been investigated by UV/visible spectroscopy and stopped flow methods at pH 7.4 and 22 degrees C, using the chloramines of the model compound 4-imidazoleacetic acid and N-alpha-acetyl-histidine [4].
  • We previously showed that imidazoleacetic acid (IAA), a GABA agonist, and histamine's metabolite in the periphery, is present in brain where its concentration increased after inhibition of HMT [5].
  • Imidazoleacetic acid (IAA) was unequivocally demonstrated in rat brain, human CSF, and human plasma by a gas chromatographic-mass spectrometric method that can reliably quantify as little as 8 pmol, i.e., 1 ng [6].
  • Most notably, the partial agonists, (+/-)-trans-2-(aminomethyl)cyclopropanoic acid ((+/-)-TAMP) and imidazole-4-acetic acid (I4AA) were converted to antagonists at rho1P2'G and rho1P2'S receptors and the partial agonist CACA acted as an antagonist at rho1P2'S receptors [7].

Biological context of C02835


Anatomical context of C02835


Associations of C02835 with other chemical compounds


Gene context of C02835

  • However, histamine's oxidative metabolite in the periphery, imidazoleacetic acid (IAA), is also present in brain and CSF, and its levels in brain increase after inhibition of HMT [17].

Analytical, diagnostic and therapeutic context of C02835

  • A sensitive method for the simultaneous determination of urinary imidazoleacetic acid and N tau- and N pi-methylimidazoleacetic acids which employs high-performance liquid chromatography with fluorescence detection is described [18].
  • Of clinical relevance also is the impaired inactivation of increased brain Hm by antimalarials such as the widely used aminoisoquinolines leading to elevated brain levels of imidazole-4-acetic acid (IAA), a potent inducer of a sleep-like state often accompanied by seizures, analgesia, decreased blood pressure and other effects [19].


  1. Histamine in the insect nervous system: distribution, synthesis and metabolism. Elias, M.S., Evans, P.D. J. Neurochem. (1983) [Pubmed]
  2. Letter: Huntington's disease: treatment with imidazole-4-acetic acid. Shoulson, I., Chase, T.N., Roberts, E., Van Balgooy, J.N. N. Engl. J. Med. (1975) [Pubmed]
  3. Presence and measurement of methylimidazoleacetic acids in brain and body fluids. Khandelwal, J.K., Hough, L.B., Pazhenchevsky, B., Morrishow, A.M., Green, J.P. J. Biol. Chem. (1982) [Pubmed]
  4. Kinetic analysis of the role of histidine chloramines in hypochlorous acid mediated protein oxidation. Pattison, D.I., Davies, M.J. Biochemistry (2005) [Pubmed]
  5. Disposition of histamine, its metabolites, and pros-methylimidazoleacetic acid in brain regions of rats chronically infused with alpha-fluoromethylhistidine. Prell, G.D., Douyon, E., Sawyer, W.F., Morrishow, A.M. J. Neurochem. (1996) [Pubmed]
  6. Presence and measurement of imidazoleacetic acid, a gamma-aminobutyric acid agonist, in rat brain and human cerebrospinal fluid. Khandelwal, J.K., Prell, G.D., Morrishow, A.M., Green, J.P. J. Neurochem. (1989) [Pubmed]
  7. Mutations of the 2' proline in the M2 domain of the human GABAC rho1 subunit alter agonist responses. Carland, J.E., Moore, A.M., Hanrahan, J.R., Mewett, K.N., Duke, R.K., Johnston, G.A., Chebib, M. Neuropharmacology (2004) [Pubmed]
  8. Baclofen selectively inhibits transmission at synapses made by axons of CA3 pyramidal cells in the hippocampal slice. Ault, B., Nadler, J.V. J. Pharmacol. Exp. Ther. (1982) [Pubmed]
  9. The effects of imidazole-4-acetic acid upon the energy metabolism of normoxic and hypoxic rat brain. MacMillan, V. Brain Res. (1982) [Pubmed]
  10. Ontogenesis of GABA receptor sites in chick embryo cerebellum. Fiszer De Plazas, S. Brain Res. (1982) [Pubmed]
  11. The effects of imidazole-4-acetic acid on cerebral carbohydrate metabolism. Bovell, M., Chung, T., MacMillan, V., Shankaran, R. Can. J. Physiol. Pharmacol. (1982) [Pubmed]
  12. A comparison of the effects of GABA, 3-aminopropanesulphonic acid and imidazoleacetic acid on the frog spinal cord. Nistri, A., Corradetti, R. Neuropharmacology (1978) [Pubmed]
  13. A comparison of gamma-aminobutyric acid and the semi-rigid analogues 4-aminotetrolic acid, 4-aminocrotonic acid and imidazole-4-acetic acid on the isolated superior cervical ganglion of the rat. Bowery, N.G., Jones, G.P. Br. J. Pharmacol. (1976) [Pubmed]
  14. Rapid determination of histamine and its metabolites in mice hair by ultra-performance liquid chromatography with time-of-flight mass spectrometry. Kawanishi, H., Toyo'oka, T., Ito, K., Maeda, M., Hamada, T., Fukushima, T., Kato, M., Inagaki, S. Journal of chromatography. A. (2006) [Pubmed]
  15. Effects of central imidazolinergic and alpha2-adrenergic activation on water intake. Sugawara, A.M., Miguel, T.T., Pereira, D.T., Menani, J.V., De Luca, L.A. Braz. J. Med. Biol. Res. (2001) [Pubmed]
  16. Diamine oxidase activity and imidazoleacetic acid formation in the foetal and maternal guinea pig liver. Fogel, W.A., Biegański, T., Bechtold, E., Maśliński, C. Agents Actions (1982) [Pubmed]
  17. Imidazoleacetic acid, a gamma-aminobutyric acid receptor agonist, can be formed in rat brain by oxidation of histamine. Thomas, B., Prell, G.D. J. Neurochem. (1995) [Pubmed]
  18. Simultaneous determination of imidazoleacetic acid and N tau- and N pi-methylimidazoleacetic acids in human urine by high-performance liquid chromatography with fluorescence detection. Tsuruta, Y., Tomida, H., Kohashi, K., Ohkura, Y. J. Chromatogr. (1987) [Pubmed]
  19. Increased plasma levels of histidine and histamine in falciparum malaria: relevance to severity of infection. Enwonwu, C.O., Afolabi, B.M., Salako, L.O., Idigbe, E.O., Bashirelah, N. Journal of neural transmission (Vienna, Austria : 1996) (2000) [Pubmed]
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