Normetanefrina

Normetanefrina
	Struttura chimica della normetanefrina
Nome IUPAC
	4-(2-amino-1-idrossi-etile)- 2-metossi-fenolo
Caratteristiche generali
Formula bruta o molecolare	C9H13NO3
Massa molecolare (u)	183.204
Numero CAS	97-31-4
PubChem	1237
SMILES	COC1=C(C=CC(=C1)C(CN)O)O
Indicazioni di sicurezza
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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

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

Bibliografia

Anton AH, Sayre DF. J Pharmacol Exp Ther. 1966 Jul;153(1):15-29. Distribution of metanephrine and normetanephrine in various animals and their analysis in diverse biologic material. PMID 5921354
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
Griffin A, O'Shea P, FitzGerald R, O'Connor G, Tormey W. Ann Clin Biochem. 2011 Jan;48(Pt 1):41-4. Epub 2010 Dec 1. Establishment of a paediatric age-related reference interval for the measurement of urinary total fractionated metanephrines. PMID 21123298
Iwaoka T, Umeda T, Sato T. Nippon Rinsho. 1989 Dec;48 Suppl:1186-9. Japanese. Clinical significance of metanephrine and normetanephrine analysis in endocrine tests of the adrenal medulla and sympathetic nervous system. PMID 2621844
Käser H, Türler K, Burri PH. Schweiz Med Wochenschr. 1971 Apr 3;101(13):484-7. German. Catecholamine metabolism in the tissue of malignant and benign tumors of the sympathetic nervous system. PMID 5558918
Murakami M, Tomita K. Nippon Rinsho. 1999 Dec;57 Suppl:219-22. Review. Japanese. Metanephrine (M) and normetanephrine (NM). PMID 10778105
Bertani LM, Dziedzic SW, Clarke DD, Gitlow SE. Clin Chim Acta. 1970 Nov;30(2):227-33. A gas-liquid chromatographic method for the separation and quantitation of normetanephrine and metanephrine in human urine. PMID 5478310
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

Portale Chimica

Portale Medicina

[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"

[1]

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