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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:57:09 UTC
HMDB IDHMDB0000819
Secondary Accession Numbers
  • HMDB00819
Metabolite Identification
Common NameNormetanephrine
DescriptionNormetanephrine, also known as normetadrenaline or N111, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Normetanephrine is a solid that is soluble in water. Normetanephrine is a metabolite of norepinephrine created by action of catechol-O-methyl transferase on norepinephrine. Within humans, normetanephrine participates in a number of enzymatic reactions. In particular, normetanephrine can be converted into 3-methoxy-4-hydroxyphenylglycolaldehyde through its interaction with the enzyme amine oxidase [flavin-containing] A. It is also involved in the metabolic disorder called transient tyrosinemia of the newborn. This compound is excreted in the urine and is found in certain tissues. It is a marker for catecholamine-secreting tumors such as pheochromocytoma (PMID: 30538672 ).
Structure
Data?1582752158
Synonyms
ValueSource
(+/-)-normetanephrineHMDB
(+/-)-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 MethoxynoradrenalineHMDB
3-MethoxynoradrenalineHMDB
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
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point204 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.05HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability19.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.3431661259
DarkChem[M-H]-136.96231661259
AllCCS[M+H]+141.5532859911
AllCCS[M-H]-139.64932859911
DeepCCS[M+H]+138.06730932474
DeepCCS[M-H]-135.57530932474
DeepCCS[M-2H]-171.18630932474
DeepCCS[M+Na]+146.43730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NormetanephrineCOC1=CC(=CC=C1O)C(O)CN2905.2Standard polar33892256
NormetanephrineCOC1=CC(=CC=C1O)C(O)CN1732.8Standard non polar33892256
NormetanephrineCOC1=CC(=CC=C1O)C(O)CN1716.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Normetanephrine,1TMS,isomer #1COC1=CC(C(O)CN)=CC=C1O[Si](C)(C)C1829.6Semi standard non polar33892256
Normetanephrine,1TMS,isomer #2COC1=CC(C(CN)O[Si](C)(C)C)=CC=C1O1749.6Semi standard non polar33892256
Normetanephrine,1TMS,isomer #3COC1=CC(C(O)CN[Si](C)(C)C)=CC=C1O1913.0Semi standard non polar33892256
Normetanephrine,2TMS,isomer #1COC1=CC(C(CN)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1769.9Semi standard non polar33892256
Normetanephrine,2TMS,isomer #2COC1=CC(C(O)CN[Si](C)(C)C)=CC=C1O[Si](C)(C)C1889.9Semi standard non polar33892256
Normetanephrine,2TMS,isomer #3COC1=CC(C(CN[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O1818.7Semi standard non polar33892256
Normetanephrine,2TMS,isomer #4COC1=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O2055.9Semi standard non polar33892256
Normetanephrine,3TMS,isomer #1COC1=CC(C(CN[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1806.7Semi standard non polar33892256
Normetanephrine,3TMS,isomer #1COC1=CC(C(CN[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1928.6Standard non polar33892256
Normetanephrine,3TMS,isomer #1COC1=CC(C(CN[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2102.6Standard polar33892256
Normetanephrine,3TMS,isomer #2COC1=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2060.8Semi standard non polar33892256
Normetanephrine,3TMS,isomer #2COC1=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2092.4Standard non polar33892256
Normetanephrine,3TMS,isomer #2COC1=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2295.0Standard polar33892256
Normetanephrine,3TMS,isomer #3COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O2045.1Semi standard non polar33892256
Normetanephrine,3TMS,isomer #3COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O2148.0Standard non polar33892256
Normetanephrine,3TMS,isomer #3COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O2262.5Standard polar33892256
Normetanephrine,4TMS,isomer #1COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2094.8Semi standard non polar33892256
Normetanephrine,4TMS,isomer #1COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2068.0Standard non polar33892256
Normetanephrine,4TMS,isomer #1COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2074.0Standard polar33892256
Normetanephrine,1TBDMS,isomer #1COC1=CC(C(O)CN)=CC=C1O[Si](C)(C)C(C)(C)C2061.9Semi standard non polar33892256
Normetanephrine,1TBDMS,isomer #2COC1=CC(C(CN)O[Si](C)(C)C(C)(C)C)=CC=C1O2021.1Semi standard non polar33892256
Normetanephrine,1TBDMS,isomer #3COC1=CC(C(O)CN[Si](C)(C)C(C)(C)C)=CC=C1O2164.5Semi standard non polar33892256
Normetanephrine,2TBDMS,isomer #1COC1=CC(C(CN)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2264.0Semi standard non polar33892256
Normetanephrine,2TBDMS,isomer #2COC1=CC(C(O)CN[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2376.4Semi standard non polar33892256
Normetanephrine,2TBDMS,isomer #3COC1=CC(C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O2316.7Semi standard non polar33892256
Normetanephrine,2TBDMS,isomer #4COC1=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2500.1Semi standard non polar33892256
Normetanephrine,3TBDMS,isomer #1COC1=CC(C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2527.4Semi standard non polar33892256
Normetanephrine,3TBDMS,isomer #1COC1=CC(C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2550.6Standard non polar33892256
Normetanephrine,3TBDMS,isomer #1COC1=CC(C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2482.3Standard polar33892256
Normetanephrine,3TBDMS,isomer #2COC1=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2763.3Semi standard non polar33892256
Normetanephrine,3TBDMS,isomer #2COC1=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2712.9Standard non polar33892256
Normetanephrine,3TBDMS,isomer #2COC1=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2587.1Standard polar33892256
Normetanephrine,3TBDMS,isomer #3COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O2702.8Semi standard non polar33892256
Normetanephrine,3TBDMS,isomer #3COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O2736.7Standard non polar33892256
Normetanephrine,3TBDMS,isomer #3COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O2550.9Standard polar33892256
Normetanephrine,4TBDMS,isomer #1COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2941.6Semi standard non polar33892256
Normetanephrine,4TBDMS,isomer #1COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2813.2Standard non polar33892256
Normetanephrine,4TBDMS,isomer #1COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2510.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Normetanephrine GC-MS (4 TMS)splash10-00di-2920000000-906a2c3ec3c929834c7b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Normetanephrine GC-MS (Non-derivatized)splash10-00di-2920000000-906a2c3ec3c929834c7b2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9600000000-df1660d54bc99d55b9bb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1900000000-f8b939907bf23331b83f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014i-0900000000-cb28fbf84eae6ad4628e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-05e9-4900000000-65aa73bd819270237f342012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9200000000-de463de74a0d6a9bfdb12012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 40V, Positive-QTOFsplash10-004i-9200000000-efafce5afe4a7c15067b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 20V, Positive-QTOFsplash10-05ai-1900000000-93cae41cf9bbc8fb06fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 10V, Positive-QTOFsplash10-014i-0900000000-4f226dd2298708c36b4d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 35V, Positive-QTOFsplash10-0h3s-5900000000-7420f0a05449387c69eb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 10V, Positive-QTOFsplash10-014i-0900000000-fa66b6a75bb70a6e11cb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 20V, Positive-QTOFsplash10-05ai-1900000000-7eaa1d030beaeae5118f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 35V, Negative-QTOFsplash10-0002-0900000000-c2a7cb2d1889ec69b26a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 40V, Positive-QTOFsplash10-004i-9300000000-98a0488cc1211d99fa572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 10V, Negative-QTOFsplash10-0002-0900000000-9997c3e9112e4558aa632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 20V, Negative-QTOFsplash10-006t-0900000000-bd5a22c7a438d15be4bc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 40V, Negative-QTOFsplash10-00dl-7900000000-863bf83793f05b65058a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 35V, Negative-QTOFsplash10-0002-0900000000-2a2538378e0bbcaed15f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Normetanephrine 35V, Negative-QTOFsplash10-0002-0900000000-4414d75b49a2cc82bdb62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normetanephrine 10V, Positive-QTOFsplash10-0159-0900000000-b19888f59670d542cc352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normetanephrine 20V, Positive-QTOFsplash10-014j-0900000000-26872ea42b5102a407ff2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normetanephrine 40V, Positive-QTOFsplash10-0fdt-4900000000-2416e3adcd40b107923d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normetanephrine 10V, Negative-QTOFsplash10-001i-0900000000-f95a5de2b99b6807a9ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normetanephrine 20V, Negative-QTOFsplash10-0gx0-0900000000-e2ba422610b39356fe572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normetanephrine 40V, Negative-QTOFsplash10-0ab9-3900000000-f9f0aaa8b3c0fcfee29a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normetanephrine 10V, Positive-QTOFsplash10-001i-0900000000-ec4dd90d9b4a388fca9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normetanephrine 20V, Positive-QTOFsplash10-001i-2900000000-f0ee1c53996f65eaa5cc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normetanephrine 40V, Positive-QTOFsplash10-0zgi-9300000000-91b1e27073d44d8f50252021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Adrenal Gland
  • Adrenal Medulla
  • Brain
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 QuantifiedNot QuantifiedChildren (6 - 18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (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 Quantified0.0340-0.182 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.00100-0.0180 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0920-0.824 umol/mmol creatinineChildren (1-13 years old)Female
Normal
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.000846 +/- 0.00037 uMNot SpecifiedNot SpecifiedAlcohol abstinence details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000185 +/- 0.00004424 uMNot SpecifiedNot Specifiedpheochromocytoma details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00004533 +/- 0.00001256 uMNot SpecifiedNot SpecifiedPrimary hypertension details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
UrineDetected and Quantified0.392-0.666 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome details
UrineDetected and Quantified0.0520-0.0780 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome details
UrineDetected and Quantified0.016 umol/mmol creatinineChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency
details
UrineDetected and Quantified0.055 umol/mmol creatinineInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency
details
Associated Disorders and Diseases
Disease References
Pheochromocytoma
  1. Foti A, Adachi M, DeQuattro V: The relationships of free to conjugated normetanephrine in plasma and spinal fluid of hypertensive patients. J Clin Endocrinol Metab. 1982 Jul;55(1):81-5. [PubMed:7076810 ]
Essential hypertension
  1. Foti A, Adachi M, DeQuattro V: The relationships of free to conjugated normetanephrine in plasma and spinal fluid of hypertensive patients. J Clin Endocrinol Metab. 1982 Jul;55(1):81-5. [PubMed:7076810 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Aromatic L-amino acid decarboxylase deficiency
  1. Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Brunner Syndrome
  1. Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022265
KNApSAcK IDC00037562
Chemspider ID1200
KEGG Compound IDC05589
BioCyc IDNot Available
BiGG ID46080
Wikipedia LinkNormetanephrine
METLIN ID66
PubChem Compound1237
PDB IDNot Available
ChEBI ID144308
Food Biomarker OntologyNot Available
VMH IDNORMETE_L
MarkerDB IDMDB00000260
Good Scents IDNot Available
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 ]
  16. Alrezk R, Suarez A, Tena I, Pacak K: Update of Pheochromocytoma Syndromes: Genetics, Biochemical Evaluation, and Imaging. Front Endocrinol (Lausanne). 2018 Nov 27;9:515. doi: 10.3389/fendo.2018.00515. eCollection 2018. [PubMed:30538672 ]

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