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Chemical Compound Review

NORMETANEPHRINE     4-(2-amino-1-hydroxy-ethyl)- 2-methoxy-phenol

Synonyms: CHEMBL774, SureCN137755, AG-C-58214, HMDB00819, CPD-11875, ...
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Disease relevance of NORMETANEPHRINE


Psychiatry related information on NORMETANEPHRINE


High impact information on NORMETANEPHRINE


Chemical compound and disease context of NORMETANEPHRINE


Biological context of NORMETANEPHRINE

  • The disproportionate decrease in excretion of normetanephrine by patients with MSA is consistent with observations in experimental animals that O-methylation is the primary metabolic route for active released norepinephrine, whereas deamination is the predominant metabolic route for intraneuronal degradation of the catecholamine [16].
  • Plasma NMN (r = 0.27; P = 0.02) but not MN positively correlated with age, whereas only plasma catecholamines (and not metanephrines) were positively correlated (P <0.05) with diastolic blood pressure [17].
  • In this method for measuring metanephrine and normetanephrine in urine, they are freed from their conjugates by hydrolysis in acid, neutralized, and isolated on a cation-exchange resin [18].
  • The level of the initial methylation product, normetanephrine, also showed a biphasic decline, which did not correspond to that of [3H]noradrenaline but rather was faster throughout the experiment [19].
  • 4. NA (10(-2) M by pressure ejection) did not alter membrane potential even in the presence of NMN and DMI (each 10(-6) M) [20].

Anatomical context of NORMETANEPHRINE


Associations of NORMETANEPHRINE with other chemical compounds



  • The excretion of normetanephrine, a marker for sympathetic nervous activity, was reduced during ST in COX-1(+/+) (6.9+/-0.9 versus 3.2+/-0.6 g . g(-1) creatinine . 10(-3); P<0.01) [31].
  • Normetanephrine, the COMT-dependent metabolite of NE, was formed in large quantities during post-uptake incubation [32].
  • The trauma patients differed from the elective neurosurgery patients with regard to D-dimer levels, PT, PTT, protein C levels, and urinary normetanephrine concentrations [33].
  • 4. Both clorgyline (a selective MAO-A inhibitor) and selegiline (a selective MAO-B inhibitor) reduced the formation of dihydroxyphenylglycol (DOPEG), DOMA and O-methylated-deaminated metabolites (OMDA), and increased that of normetanephrine (NMN) [34].
  • A cytosol fraction of chorio-decidua was incubated with [14C]-S-adenosyl-L-methionine and normetanephrine for 60 min to measure PNMT activity [35].

Analytical, diagnostic and therapeutic context of NORMETANEPHRINE


  1. Plasma normetanephrine and metanephrine for detecting pheochromocytoma in von Hippel-Lindau disease and multiple endocrine neoplasia type 2. Eisenhofer, G., Lenders, J.W., Linehan, W.M., Walther, M.M., Goldstein, D.S., Keiser, H.R. N. Engl. J. Med. (1999) [Pubmed]
  2. The relationships of free to conjugated normetanephrine in plasma and spinal fluid of hypertensive patients. Foti, A., Adachi, M., DeQuattro, V. J. Clin. Endocrinol. Metab. (1982) [Pubmed]
  3. Pheochromocytomas in von Hippel-Lindau syndrome and multiple endocrine neoplasia type 2 display distinct biochemical and clinical phenotypes. Eisenhofer, G., Walther, M.M., Huynh, T.T., Li, S.T., Bornstein, S.R., Vortmeyer, A., Mannelli, M., Goldstein, D.S., Linehan, W.M., Lenders, J.W., Pacak, K. J. Clin. Endocrinol. Metab. (2001) [Pubmed]
  4. Determination of urinary normetanephrine and metanephrine by radial-compression liquid chromatography and electrochemical detection. Orsulak, P.J., Kizuka, P., Grab, E., Schildkraut, J.J. Clin. Chem. (1983) [Pubmed]
  5. Adrenocortical, autonomic, and inflammatory causes of the metabolic syndrome: nested case-control study. Brunner, E.J., Hemingway, H., Walker, B.R., Page, M., Clarke, P., Juneja, M., Shipley, M.J., Kumari, M., Andrew, R., Seckl, J.R., Papadopoulos, A., Checkley, S., Rumley, A., Lowe, G.D., Stansfeld, S.A., Marmot, M.G. Circulation (2002) [Pubmed]
  6. Urinary excretion of metabolites of norepinephrine in Tourette's syndrome. Baker, G.B., Bornstein, R.A., Douglass, A.B., Carroll, A., King, G. Mol. Chem. Neuropathol. (1990) [Pubmed]
  7. In situ analysis of alpha-adrenoceptors on arteriolar and venular smooth muscle in rat skeletal muscle microcirculation. Faber, J.E. Circ. Res. (1988) [Pubmed]
  8. Phenotypic properties of catecholamine-positive cells that differentiate in avian neural crest cultures. Christie, D.S., Forbes, M.E., Maxwell, G.D. J. Neurosci. (1987) [Pubmed]
  9. Identification of alpha-adrenergic receptors in uterine smooth muscle membranes by [3H]dihydroergocryptine binding. Williams, L.T., Mullikin, D., Lefkowitz, R.J. J. Biol. Chem. (1976) [Pubmed]
  10. Detecting pheochromocytoma: defining the most sensitive test. Guller, U., Turek, J., Eubanks, S., Delong, E.R., Oertli, D., Feldman, J.M. Ann. Surg. (2006) [Pubmed]
  11. Toward a rapidly acting antidepressant: the normetanephrine and extraneuronal monoamine transporter (uptake 2) hypothesis. Schildkraut, J.J., Mooney, J.J. The American journal of psychiatry. (2004) [Pubmed]
  12. Biochemical and clinical manifestations of dopamine-producing paragangliomas: utility of plasma methoxytyramine. Eisenhofer, G., Goldstein, D.S., Sullivan, P., Csako, G., Brouwers, F.M., Lai, E.W., Adams, K.T., Pacak, K. J. Clin. Endocrinol. Metab. (2005) [Pubmed]
  13. Remarkably suppressed manganese superoxide dismutase activity in malignant pheochromocytoma. Nakada, T., Kubota, Y., Sasagawa, I., Yagisawa, T., Watanabe, M., Ishigooka, M. J. Urol. (1995) [Pubmed]
  14. Analysis of urinary metanephrines by reversed-phase high-performance liquid chromatography and electrochemical detection. Bertani-Dziedzic, L.M., Krstulovic, A.M., Dziedzic, S.W., Gitlow, S.E., Cerqueira, S. Clin. Chim. Acta (1981) [Pubmed]
  15. Adrenal incidentaloma: review of 197 patients and report of a drug-related false-positive urinary normetanephrine result. Ito, T., Imai, T., Kikumori, T., Shibata, A., Horiba, T., Kobayashi, H., Sawaki, M., Watanabe, R., Nakao, A., Kiuchi, T. Surg. Today (2006) [Pubmed]
  16. Urinary catecholamine metabolites distinguish different types of sympathetic neuronal dysfunction in patients with orthostatic hypotension. Kopin, I.J., Polinsky, R.J., Oliver, J.A., Oddershede, I.R., Ebert, M.H. J. Clin. Endocrinol. Metab. (1983) [Pubmed]
  17. Quantification of unconjugated metanephrines in human plasma without interference by acetaminophen. Roden, M., Raffesberg, W., Raber, W., Bernroider, E., Niederle, B., Waldhäusl, W., Gasic, S. Clin. Chem. (2001) [Pubmed]
  18. Urinary metanephrines as measured by liquid chromatography with an on-line post-column reaction detector. Flood, J.G., McComb, R.B. Clin. Chem. (1981) [Pubmed]
  19. Time course of the metabolite patterns of intraventricularly injected [3H]noradrenaline in rat brain regions. Köster, G. J. Neurochem. (1986) [Pubmed]
  20. The electrical and mechanical responses of the rabbit saphenous artery to nerve stimulation and drugs. Nally, J.E., Muir, T.C. Br. J. Pharmacol. (1992) [Pubmed]
  21. Adipocyte beta-adrenergic receptors. Identification and subcellular localization by (-)-[3H]dihydroalprenolol binding. Williams, L.T., Jarett, L., Lefkowitz, R.J. J. Biol. Chem. (1976) [Pubmed]
  22. Conjugated normetanephrine in human and rat plasma and erythrocytes. Yoneda, S., Alexander, N., Vlachakis, N.D. Biochem. Pharmacol. (1984) [Pubmed]
  23. Microinjection of opioids into the nucleus reticularis gigantocellularis of the rat: analgesia and increase in the normetanephrine level in the spinal cord. Kuraishi, Y., Fukui, K., Shiomi, H., Akaike, A., Takagi, H. Biochem. Pharmacol. (1978) [Pubmed]
  24. Destruction of meningeal cells over the medial cerebral hemisphere of newborn hamsters prevents the formation of the infrapyramidal blade of the dentate gyrus. Hartmann, D., Sievers, J., Pehlemann, F.W., Berry, M. J. Comp. Neurol. (1992) [Pubmed]
  25. Urinary monoamines and monoamine metabolites in subtypes of unipolar depressive disorder and normal controls. Roy, A., Pickar, D., Douillet, P., Karoum, F., Linnoila, M. Psychological medicine. (1986) [Pubmed]
  26. Urinary metanephrine and normetanephrine determined without extraction by using liquid chromatography and coulometric array detection. Gamache, P.H., Kingery, M.L., Acworth, I.N. Clin. Chem. (1993) [Pubmed]
  27. Measurement of urinary metanephrines to screen for pheochromocytoma in an unselected hospital referral population. Brain, K.L., Kay, J., Shine, B. Clin. Chem. (2006) [Pubmed]
  28. Urinary catecholamines in attention-deficit hyperactivity disorder with and without comorbid anxiety. Pliszka, S.R., Maas, J.W., Javors, M.A., Rogeness, G.A., Baker, J. Journal of the American Academy of Child and Adolescent Psychiatry. (1994) [Pubmed]
  29. Catecholamine functioning in children with traumatic brain injuries and children with attention-deficit/hyperactivity disorder. Konrad, K., Gauggel, S., Schurek, J. Brain research. Cognitive brain research. (2003) [Pubmed]
  30. Kinetic analyses of the mechanisms of action of inhibitors of the extraneuronal uptake of adrenaline in smooth muscle cells of guinea-pig trachea. Bryan, L.J., O'Donnell, S.R. Naunyn Schmiedebergs Arch. Pharmacol. (1981) [Pubmed]
  31. Cyclooxygenase-1-deficient mice have high sleep-to-wake blood pressure ratios and renal vasoconstriction. Kawada, N., Solis, G., Ivey, N., Connors, S., Dennehy, K., Modlinger, P., Hamel, R., Kawada, J.T., Imai, E., Langenbach, R., Welch, W.J., Wilcox, C.S. Hypertension (2005) [Pubmed]
  32. Catechol-O-methyltransferase activity in CHO cells expressing norepinephrine transporter. Percy, E., Kaye, D.M., Lambert, G.W., Gruskin, S., Esler, M.D., Du, X.J. Br. J. Pharmacol. (1999) [Pubmed]
  33. Coagulopathy and catecholamines in severe head injury. Kearney, T.J., Bentt, L., Grode, M., Lee, S., Hiatt, J.R., Shabot, M.M. The Journal of trauma. (1992) [Pubmed]
  34. The role of MAO-A and MAO-B in the metabolic degradation of noradrenaline in human arteries. Figueiredo, I.V., Caramona, M., Paiva, M.Q., Guimarães, S. Journal of autonomic pharmacology. (1998) [Pubmed]
  35. Effect of labor and prostaglandins on phenylethanolamine N-methyltransferase in human fetal membranes. Morimoto, T., Sekizawa, A., Hirose, K., Suzuki, A., Saito, H., Yanaihara, T. Endocr. J. (1993) [Pubmed]
  36. Urinary normetanephrine and metanephrine measured by radioimmunoassay for the diagnosis of pheochromocytoma: utility of 24-hour and random 1-hour urine determinations. Oishi, S., Sasaki, M., Ohno, M., Sato, T. J. Clin. Endocrinol. Metab. (1988) [Pubmed]
  37. Sympathetic activity and cardiac adrenergic receptors in one-kidney, one clip hypertension in rats. Vlachakis, N.D., Ransom, F., Kogosov, E., Woodcock, E., Alexander, N., Maronde, R.F. Hypertension (1984) [Pubmed]
  38. Determination of metanephrines in plasma by liquid chromatography with electrochemical detection. Lenders, J.W., Eisenhofer, G., Armando, I., Keiser, H.R., Goldstein, D.S., Kopin, I.J. Clin. Chem. (1993) [Pubmed]
  39. Evaluation of urinary metanephrine and normetanephrine enzyme immunoassay (ELISA) kits by comparison with isotope dilution mass spectrometry. Wolthers, B.G., Kema, I.P., Volmer, M., Wesemann, R., Westermann, J., Manz, B. Clin. Chem. (1997) [Pubmed]
  40. Urinary catecholamines before and after tracheostomy in patients with obstructive sleep apnea and hypertension. Fletcher, E.C., Miller, J., Schaaf, J.W., Fletcher, J.G. Sleep. (1987) [Pubmed]
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