Normetanefrina

Normetanefrina
Struttura chimica della normetanefrina
Struttura chimica della normetanefrina
Nome IUPAC
4-(2-amino-1-idrossi-etile)- 2-metossi-fenolo
Caratteristiche generali
Formula bruta o molecolareC9H13NO3
Massa molecolare (u)183.204
Numero CAS97-31-4
PubChem1237
SMILES
COC1=C(C=CC(=C1)C(CN)O)O
Indicazioni di sicurezza
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La via di degradazione della noradrenalina, con la normetanefrina in alto a sinistra

La normetanefrina 4-(2-amino-1-idrossi-etile)- 2-metossi-fenolo è un metabolita intermedio del metabolismo delle catecolamine, si viene a formare in seguito all'azione dell'enzima catecol-O-metilasi sulla noradrenalina[1].

Sia la normetanefrina che la metanefrina vengono espulse nelle urine ed il loro dosaggio le rende un marcatore per i tumori secernenti catecolamine, come il feocromocitoma. Assieme alla metanefrina rappresenta il 20-40% dei cataboliti urinari provenienti dal metabolismo delle catecolamine[2].

Marcatore tumorale

I valori normali di metanefrina e normetanefrina, prendendo a riferimento le urine delle 24h sono compresi fra i 310-510 µg/24, un loro innalzamento viene associato all'insorgenza di feocromocitomi, sono possibili falsi positivi in quanto i valori di tali molecole nel sangue possono innalzarsi anche a seguito di terapie con IMAO, catecolamine, L-Dopa, beta-bloccanti e nei soggetti affetti da etilismo cronico.

Note

  1. ^ D. Andreani,G. Menzinger, D. Andreani; (1984) "Trattato di diagnostica funzionale endocrinologica" ISBN 88-299-0196-2
  2. ^ M. Mannelli1, T. Ercolino1, L. Becherini1, G. Bernini2, L. Simi1, G. Parenti1; Ligand Assay (2006); "Diagnosi genetica e biochimica del ferocromocitoma"

Bibliografia

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  • Sato T, Yoshinaga K. Tohoku J Exp Med. 1973 Jul;110(3):283-7. A metanephrine test for a screening of catecholamine-producing tumors. PMID 4757670
  • Eisenhofer G, Lenders JW. Adv Pharmacol. 1998;42:374-7. Clues to the diagnosis of pheochromocytoma from the differential tissue metabolism of catecholamines. PMID 9327920
  • Shimbo S. Naika Hokan. 1968 Sep;15(9):299-310. Japanese. Clinical studies on urinary metanephrine and normetanephrine in various endocrine diseases. 2. Clinical studies on urinary metanephrine and normetanephrine in patients with pheochromyocytoma and a patient with neuroblastoma. PMID 5752086
  • Wolf RL, Gherman CE, Lauer JD, Fish HL, Levey BR. Clin Sci Mol Med Suppl. 1973 Aug;45 Suppl 1:263s-7. A new urinary assay for separate normetanephrine and metanephrine with application for the diagnosis of phaeochromocytoma. PMID 4522173
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  • Yaworsky DC, Wu AH, Hill DW. Clin Chim Acta. 2005 Mar;353(1-2):31-44. The use of plasma metanephrine to normetanephrine ratio to determine epinephrine poisoning. PMID 15698588
  • Eisenhofer G, Lenders JW, Goldstein DS, Mannelli M, Csako G, Walther MM, Brouwers FM, Pacak K. Clin Chem. 2005 Apr;51(4):735-44. Epub 2005 Feb 17. Pheochromocytoma catecholamine phenotypes and prediction of tumor size and location by use of plasma free metanephrines. PMID 15718487
  • Lando LI, Krupenina LB, Aziavchik AV. Vopr Med Khim. 1973 Sep-Oct;19(5):501-5. Russian. Adrenaline and noradrenaline concentrations in rat tissues in different phases of single and repeated electroconvulsive seizures. PMID 4788174
  • Raum WJ. Methods Enzymol. 1987;142:550-71. Enzymatic radioimmunoassay of epinephrine, norepinephrine, metanephrine, and normetanephrine. PMID 3600381
  • Steinberg AB. Biol Psychol. 1974;2(2):135-49. Individual patterns of excretion of metanephrine and normetanephrine by children. PMID 4475599
  • Bigelow LB, Dairman W, Weil-Malherbe H, Udenfriend S. Mol Pharmacol. 1969 Nov;5(6):565-71. Increased synthesis of catecholamines and their metabolites following the administration of phenoxybenzamine. PMID 5373892
  • Canfell C, Binder SR, Khayam-Bashi H. Clin Chem. 1982 Jan;28(1):25-8. Quantitation of urinary normetanephrine and metanephrine by reversed-phase extraction and mass-fragmentographic analysis. PMID 7055927
  • Iwata H, Fujimoto S, Nishikawa T, Hano K. Experientia. 1968 Apr 15;24(4):378-80. German. Pharmacologic studies in thiamine deficiency. I. Changes in the catecholamine content of tissues. PMID 5705198
  • Miyoshi T, Tomita K.Nippon Rinsho. 2005 Aug;63 Suppl 8:395-8. Review. Japanese. Metanephrine (M), normetanephrine (NM) and fractionated metanephrines PMID 16149538

Voci correlate

  Portale Biologia