Normetanefrina

Normetanefrina
Propriedades
Fórmula química	C9H13NO3
Massa molar	183,204 g/mol

Normetanefrina
Identificadores
Número CAS	97-31-4
PubChem	1237
ChemSpider	1200
MeSH	Normetanephrine
SMILES	Oc1ccc(cc1OC)C(O)CN;
InChI	InChI=1/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3 Key:YNYAYWLBAHXHLL-UHFFFAOYAR;

Normetanefrina
Nomes
Nome IUPAC	4-(2-amino-1-hydroxy-ethyl)- 2-methoxy-phenol
Normetanefrina
Identificadores
Número CAS	97-31-4
PubChem	1237
ChemSpider	1200
MeSH	Normetanephrine
SMILES	Oc1ccc(cc1OC)C(O)CN;
InChI	InChI=1/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3 Key:YNYAYWLBAHXHLL-UHFFFAOYAR;
Normetanefrina
Propriedades
Fórmula química	C9H13NO3
Massa molar	183,204 g/mol
Página de dados suplementares
Estrutura e propriedades	n, εr, etc.
Dados termodinâmicos	Comportamento de fases; Sólido, líquido e gás
Dados espectrais	UV, IV, RMN, EM
	Exceto onde denotado, os dados referem-se a; materiais sob condições normais de temperatura e pressão.; Referências e avisos gerais sobre esta caixa.; Alerta sobre risco à saúde.

Normetanefrina, 4-(2-amino-1-hidroxi-etil)-2-metoxi-fenol, é um metabólito intermediário do metabolismo da catecolamina, metabólito da norepinefrina criado pela ação da catecol O-metiltransferase (catecol-O-metilase) sobre a norepinefrina. É excretada na urina e encontrada em certos tecidos.

Tanto a normetanefrina quanto a metanefrina são excretadas na urina e sua dosagem os torna um marcador para tumores secretores de catecolamina, como feocromocitoma. Juntamente com a metanefrina, representa 20-40% dos catabólitos urinários decorrentes do metabolismo da catecolamina. É um marcador para tumores secretores de catecolamina tais como o feocromocitoma.

Marcador tumoral

Os valores normais de metanefrina e normetanefrina, tomando-se como referência a urina de 24 horas, estão entre 310-510 µg / 24, seu aumento está associado ao aparecimento de feocromocitomas, sendo falso-positivos possíveis, pois os valores dessas moléculas no sangue também podem aumentar após tratamentos com IMAO, catecolaminas, L-Dopa, betabloqueadores e em indivíduos que sofrem de etilismo crônico.

Referências

↑ D. Andreani,G. Menzinger, D. Andreani; (1984) "Trattato di diagnostica funzionale endocrinologica" ISBN 88-299-0196-2
↑ Kambur O, Kaunisto MA, Tikkanen E, Leal SM, Ripatti S, Kalso EA. Effect of catechol-o-methyltransferase-gene (COMT) variants on experimental and acute postoperative pain in 1,000 women undergoing surgery for breast cancer. Anesthesiology. 2013 Dec;119(6):1422-33. doi: 10.1097/ALN.0000000000000013.
↑ M. Mannelli1, T. Ercolino1, L. Becherini1, G. Bernini2, L. Simi1, G. Parenti1; Ligand Assay (2006); "Diagnosi genetica e biochimica del ferocromocitoma"
↑ Figura 11-4 em: Flower, R.; Rang, H. P.; Dale, M. M.; Ritter, J. M. (2007). Rang & Dale's Pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-06911-5
↑ Brain, K. L., Kay, J., & Shine, B. (2006). Measurement of urinary metanephrines to screen for pheochromocytoma in an unselected hospital referral population. Clinical chemistry, 52(11), 2060–2064.
↑ Oishi S, Sasaki M, Ohno M, Sato T. Urinary normetanephrine and metanephrine measured by radioimmunoassay for the diagnosis of pheochromocytoma: utility of 24-hour and random 1-hour urine determinations. J Clin Endocrinol Metab. 1988 Sep;67(3):614-8.
↑ Eisenhofer, G., Walther, M., Keiser, H.R., Lenders, J.W.M., Friberg, P., & Pacak, K.. (2000). Plasma metanephrines: a novel and cost-effective test for pheochromocytoma. Brazilian Journal of Medical and Biological Research, 33(10), 1157-1169.
↑ Ogata M, Mendelson JH, Mello NK, Majchrowicz E. Adrenal function and alcoholism. II. Catecholamines.Psychosom Med. 1971 Mar-Apr;33(2):159-80. PMID: 5549660 DOI: 10.1097/00006842-197103000-00007
↑ Recent Advances in Studies of Alcoholism: An Interdisciplinary Symposium; National Institute on Alcohol Abuse and Alcoholism, 1971. pág. 152.
↑ Charles S. Lieber; Metabolic Aspects of Alcoholism. Springer Science & Business Media, 2012. pág. 266.
↑ Bulletin, Problems of Drug Dependence: Report of the Thirty-first Meeting, 24, 25, and 26 February, 1969, Palo Alto, California. National Research Council (U.S.). Committee on Problems of Drug Dependence. pág. 6276.

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

[1] D. Andreani,G. Menzinger, D. Andreani; (1984) "Trattato di diagnostica funzionale endocrinologica" ISBN 88-299-0196-2

[2] Kambur O, Kaunisto MA, Tikkanen E, Leal SM, Ripatti S, Kalso EA. Effect of catechol-o-methyltransferase-gene (COMT) variants on experimental and acute postoperative pain in 1,000 women undergoing surgery for breast cancer. Anesthesiology. 2013 Dec;119(6):1422-33. doi: 10.1097/ALN.0000000000000013.

[3] M. Mannelli1, T. Ercolino1, L. Becherini1, G. Bernini2, L. Simi1, G. Parenti1; Ligand Assay (2006); "Diagnosi genetica e biochimica del ferocromocitoma"

[Rang&Dale6th-11-4-4] Figura 11-4 em: Flower, R.; Rang, H. P.; Dale, M. M.; Ritter, J. M. (2007). Rang & Dale's Pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-06911-5

[5] Brain, K. L., Kay, J., & Shine, B. (2006). Measurement of urinary metanephrines to screen for pheochromocytoma in an unselected hospital referral population. Clinical chemistry, 52(11), 2060–2064.

[6] Oishi S, Sasaki M, Ohno M, Sato T. Urinary normetanephrine and metanephrine measured by radioimmunoassay for the diagnosis of pheochromocytoma: utility of 24-hour and random 1-hour urine determinations. J Clin Endocrinol Metab. 1988 Sep;67(3):614-8.

[7] Eisenhofer, G., Walther, M., Keiser, H.R., Lenders, J.W.M., Friberg, P., & Pacak, K.. (2000). Plasma metanephrines: a novel and cost-effective test for pheochromocytoma. Brazilian Journal of Medical and Biological Research, 33(10), 1157-1169.

[8] Ogata M, Mendelson JH, Mello NK, Majchrowicz E. Adrenal function and alcoholism. II. Catecholamines.Psychosom Med. 1971 Mar-Apr;33(2):159-80. PMID: 5549660 DOI: 10.1097/00006842-197103000-00007

[9] Recent Advances in Studies of Alcoholism: An Interdisciplinary Symposium; National Institute on Alcohol Abuse and Alcoholism, 1971. pág. 152.

[10] Charles S. Lieber; Metabolic Aspects of Alcoholism. Springer Science & Business Media, 2012. pág. 266.

[11] Bulletin, Problems of Drug Dependence: Report of the Thirty-first Meeting, 24, 25, and 26 February, 1969, Palo Alto, California. National Research Council (U.S.). Committee on Problems of Drug Dependence. pág. 6276.