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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:49:40 UTC
HMDB IDHMDB0000819
Secondary Accession Numbers
  • HMDB00819
Metabolite Identification
Common NameNormetanephrine
DescriptionNormetanephrine is a methylated metabolite of norepinephrine that is excreted in the urine and found in certain tissues. It is a marker for tumors.
Structure
Thumb
Synonyms
ValueSource
(+/-)-normetanephrineChEMBL
(+/-)-alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanolHMDB
3-Methoxy-noradrenalineHMDB
3-O-Methyl-noradrenalineHMDB
4-(2-amino-1-Hydroxyethyl)-2-methoxyphenolHMDB
alpha-(Aminomethyl)-4-hydroxy-3-methoxy-benzenemethanolHMDB
DL-N-NormetanephrineHMDB
DL-NormetanephrineHMDB
L-NormetanephrineHMDB
m-O-MethylnorepinephrineHMDB
N111HMDB
NormetadrenalineHMDB
O-MethylnoradrenalineHMDB
3 MethoxynoradrenalineMeSH
3-MethoxynoradrenalineMeSH
Chemical FormulaC9H13NO3
Average Molecular Weight183.2044
Monoisotopic Molecular Weight183.089543287
IUPAC Name4-(2-amino-1-hydroxyethyl)-2-methoxyphenol
Traditional Name(+/-)-normetanephrine
CAS Registry Number97-31-4
SMILES
COC1=CC(=CC=C1O)C(O)CN
InChI Identifier
InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3
InChI KeyYNYAYWLBAHXHLL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Ether
  • Primary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

    Endocrine gland:

  Cell and elements:

    Element:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point204 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.05HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility8.44 g/LALOGPS
logP-0.71ALOGPS
logP-0.39ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.99ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.71 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.94 m³·mol⁻¹ChemAxon
Polarizability19.1 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-2920000000-906a2c3ec3c929834c7bView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00di-2920000000-906a2c3ec3c929834c7bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-cb28fbf84eae6ad4628eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05e9-4900000000-65aa73bd819270237f34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9200000000-de463de74a0d6a9bfdb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-b19888f59670d542cc35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-26872ea42b5102a407ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdt-4900000000-2416e3adcd40b107923dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-f95a5de2b99b6807a9aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gx0-0900000000-e2ba422610b39356fe57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-3900000000-f9f0aaa8b3c0fcfee29aView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Location
  • Adrenal Gland
  • Adrenal Medulla
  • Brain
  • Platelet
Pathways
NameSMPDB/PathwhizKEGG
AlkaptonuriaPw000180Pw000180 greyscalePw000180 simpleNot Available
Disulfiram PathwayPw000431Pw000431 greyscalePw000431 simpleNot Available
Dopamine beta-hydroxylase deficiencyPw000474Pw000474 greyscalePw000474 simpleNot Available
HawkinsinuriaPw000181Pw000181 greyscalePw000181 simpleNot Available
Monoamine oxidase-a deficiency (MAO-A)Pw000509Pw000509 greyscalePw000509 simpleNot Available
Displaying entries 1 - 5 of 8 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00035 +/- 0.00016 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.00022 +/- 0.00052 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00045 +/- 0.00120 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0052 uMNot SpecifiedNot SpecifiedNormal details
FecesDetected but not Quantified Children (6 - 18 years old)BothNormal details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.85 +/- 3.17 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.00085 +/- 0.00317 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<0.322 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.062 +/- 0.037 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00093 +/- 0.00158 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
BloodDetected and Quantified0.00077 +/- 0.00129 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
BloodDetected and Quantified0.00063 +/- 0.00101 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
BloodDetected and Quantified0.00023 +/- 0.00039 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
BloodDetected and Quantified0.00029 +/- 0.00048 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
BloodDetected and Quantified0.00018 +/- 0.00029 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
BloodDetected and Quantified0.00023 +/- 0.00034 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
BloodDetected and Quantified0.00050 +/- 0.00061 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000846 +/- 0.00037 uMNot SpecifiedNot SpecifiedAlcohol abstinence details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000185 +/- 4.424e-05 uMNot SpecifiedNot Specifiedpheochromocytoma details
Cerebrospinal Fluid (CSF)Detected and Quantified4.533e-05 +/- 1.256e-05 uMNot SpecifiedNot SpecifiedPrimary hypertension details
FecesDetected but not Quantified Children (6 - 18 years old)BothCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD details
Associated Disorders and Diseases
Disease References
Amphetamine psychosis
  1. Yui K, Goto K, Ikemoto S, Ishiguro T: Plasma monoamine metabolites and spontaneous recurrence of methamphetamine-induced paranoid-hallucinatory psychosis: relation of noradrenergic activity to the occurrence of flashbacks. Psychiatry Res. 1996 Jul 31;63(2-3):93-107. [PubMed:8878306 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022265
KNApSAcK IDNot Available
Chemspider ID1200
KEGG Compound IDC05589
BioCyc IDNot Available
BiGG ID46080
Wikipedia LinkNormetanephrine
METLIN ID66
PubChem Compound1237
PDB IDNot Available
ChEBI ID144308
References
Synthesis ReferenceSejbal, Jan; Krecek, Vaclav. Method of preparing normetanephrine. Czech. (1992), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
  2. Eisenhofer G, Keiser H, Friberg P, Mezey E, Huynh TT, Hiremagalur B, Ellingson T, Duddempudi S, Eijsbouts A, Lenders JW: Plasma metanephrines are markers of pheochromocytoma produced by catechol-O-methyltransferase within tumors. J Clin Endocrinol Metab. 1998 Jun;83(6):2175-85. [PubMed:9626157 ]
  3. Wester P, Bergstrom U, Eriksson A, Gezelius C, Hardy J, Winblad B: Ventricular cerebrospinal fluid monoamine transmitter and metabolite concentrations reflect human brain neurochemistry in autopsy cases. J Neurochem. 1990 Apr;54(4):1148-56. [PubMed:1968956 ]
  4. Schmidt J, Mohr VD, Metzger P, Zirngibl H: Posttraumatic hypertension secondary to adrenal hemorrhage mimicking pheochromocytoma: case report. J Trauma. 1999 May;46(5):973-5. [PubMed:10338428 ]
  5. Eisenhofer G, Huysmans F, Pacak K, Walther MM, Sweep FC, Lenders JW: Plasma metanephrines in renal failure. Kidney Int. 2005 Feb;67(2):668-77. [PubMed:15673315 ]
  6. Orsulak PJ, Kizuka P, Grab E, Schildkraut JJ: Determination of urinary normetanephrine and metanephrine by radial-compression liquid chromatography and electrochemical detection. Clin Chem. 1983 Feb;29(2):305-9. [PubMed:6821934 ]
  7. Linos DA: Management approaches to adrenal incidentalomas (adrenalomas). A view from Athens, Greece. Endocrinol Metab Clin North Am. 2000 Mar;29(1):141-57. [PubMed:10732269 ]
  8. Oishi S, Sasaki M, Sato T, Isogai M: Coexistence of MEN 2A and papillary thyroid carcinoma and a recurrent pheochromocytoma 23 years after surgery: report of a case and a review of the Japanese literature. Jpn J Clin Oncol. 1995 Aug;25(4):153-8. [PubMed:7666591 ]
  9. Filaire E, Legrand B, Bret K, Sagnol M, Cottet-Emard JM, Pequignot JM: Psychobiologic responses to 4 days of increased training and recovery in cyclists. Int J Sports Med. 2002 Nov;23(8):588-94. [PubMed:12439775 ]
  10. Filaire E, Legrand B, Lac G, Pequignot JM: Training of elite cyclists: effects on mood state and selected hormonal responses. J Sports Sci. 2004 Nov-Dec;22(11-12):1025-33. [PubMed:15801496 ]
  11. Higa S, Suzuki T, Sakoda S, Kishimoto S, Takaba Y, Nakajima A, Markey SP: Disturbed function of the pineal gland in familial amyloid polyneuropathy. J Neural Transm. 1987;69(1-2):97-103. [PubMed:3035087 ]
  12. Eisenhofer G, Goldstein DS, Sullivan P, Csako G, Brouwers FM, Lai EW, Adams KT, Pacak K: Biochemical and clinical manifestations of dopamine-producing paragangliomas: utility of plasma methoxytyramine. J Clin Endocrinol Metab. 2005 Apr;90(4):2068-75. Epub 2005 Jan 11. [PubMed:15644397 ]
  13. Pacak K, Ilias I, Adams KT, Eisenhofer G: Biochemical diagnosis, localization and management of pheochromocytoma: focus on multiple endocrine neoplasia type 2 in relation to other hereditary syndromes and sporadic forms of the tumour. J Intern Med. 2005 Jan;257(1):60-8. [PubMed:15606377 ]
  14. Guller U, Turek J, Eubanks S, Delong ER, Oertli D, Feldman JM: Detecting pheochromocytoma: defining the most sensitive test. Ann Surg. 2006 Jan;243(1):102-7. [PubMed:16371743 ]
  15. Eisenhofer G, Lenders JW, Goldstein DS, Mannelli M, Csako G, Walther MM, Brouwers FM, Pacak K: Pheochromocytoma catecholamine phenotypes and prediction of tumor size and location by use of plasma free metanephrines. Clin Chem. 2005 Apr;51(4):735-44. Epub 2005 Feb 17. [PubMed:15718487 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + Norepinephrine → S-Adenosylhomocysteine + Normetanephrinedetails