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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:37 UTC
HMDB IDHMDB0000216
Secondary Accession Numbers
  • HMDB00216
  • HMDB0037685
  • HMDB37685
Metabolite Identification
Common NameNorepinephrine
DescriptionNorepinephrine is the precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. Norepinephrine is elevated in the urine of people who consume bananas. Norepinephrine is also a microbial metabolite; urinary noradrenaline is produced by Escherichia, Bacillus, and Saccharomyces (PMID: 24621061 ). Norepinephrine is found in alcoholic beverages, banana peels and pulp (Musa paradisiaca), red plum fruit (Prunus domestica), orange pulp (Citrus sinensis), potato tubers (Solanum tuberosum), and whole purslane (Portulaca oleracea). P. oleracea is the richest of these sources. Norepinephrine has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
Data?1676999677
Synonyms
ValueSource
(-)-ArterenolChEBI
(-)-NoradrenalineChEBI
(-)-NorepinephrineChEBI
(R)-(-)-NorepinephrineChEBI
(R)-4-(2-amino-1-Hydroxyethyl)-1,2-benzenediolChEBI
(R)-NorepinephrineChEBI
4-[(1R)-2-amino-1-Hydroxyethyl]-1,2-benzenediolChEBI
ArterenolChEBI
L-NoradrenalineChEBI
L-NorepinephrineChEBI
NoradrenalineChEBI
NorepinefrinaChEBI
NorepinephrinumChEBI
(-)-(R)-NorepinephrineHMDB
(-)-alpha-(Aminomethyl)protocatechuyl alcoholHMDB
(R)-NoradrenalineHMDB
4-(2-amino-1-Hydroxyethyl)-1,2-benzenediolHMDB
AdrenorHMDB
AktaminHMDB
L-2-amino-1-(3,4-Dihydroxyphenyl)ethanolHMDB
L-3,4-DihydroxyphenylethanolamineHMDB
L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcoholHMDB
L-ArterenolHMDB
LevarterenolHMDB, MeSH
LevoarterenolHMDB
LevonorHMDB, MeSH
LevonoradrenalineHMDB
LevonorepinephrineHMDB, MeSH
LevophedHMDB, MeSH
Nor-epirenanHMDB
NoradrenalinHMDB
NorartrinalHMDB
NorepirenamineHMDB
Sympathin EHMDB
Chemical FormulaC8H11NO3
Average Molecular Weight169.1778
Monoisotopic Molecular Weight169.073893223
IUPAC Name4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
Traditional Namenorepinephrine
CAS Registry Number51-41-2
SMILES
NC[C@H](O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
InChI KeySFLSHLFXELFNJZ-QMMMGPOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point145.2 - 146.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility849 mg/mLNot Available
LogP-1.24HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg131.98730932474
[M-H]-Not Available133.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00000287
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.5 g/LALOGPS
logP-0.68ChemAxon
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)8.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.46 m³·mol⁻¹ChemAxon
Polarizability16.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.03131661259
DarkChem[M-H]-134.39531661259
AllCCS[M+H]+138.13132859911
AllCCS[M-H]-134.92832859911
DeepCCS[M+H]+140.38630932474
DeepCCS[M-H]-137.9930932474
DeepCCS[M-2H]-173.07130932474
DeepCCS[M+Na]+147.78930932474
AllCCS[M+H]+138.132859911
AllCCS[M+H-H2O]+133.832859911
AllCCS[M+NH4]+142.132859911
AllCCS[M+Na]+143.332859911
AllCCS[M-H]-134.932859911
AllCCS[M+Na-2H]-136.132859911
AllCCS[M+HCOO]-137.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorepinephrineNC[C@H](O)C1=CC(O)=C(O)C=C13054.2Standard polar33892256
NorepinephrineNC[C@H](O)C1=CC(O)=C(O)C=C12138.8Standard non polar33892256
NorepinephrineNC[C@H](O)C1=CC(O)=C(O)C=C11905.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norepinephrine,1TMS,isomer #1C[Si](C)(C)O[C@@H](CN)C1=CC=C(O)C(O)=C11947.9Semi standard non polar33892256
Norepinephrine,1TMS,isomer #2C[Si](C)(C)OC1=CC([C@@H](O)CN)=CC=C1O1892.5Semi standard non polar33892256
Norepinephrine,1TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@@H](O)CN)C=C1O1900.6Semi standard non polar33892256
Norepinephrine,1TMS,isomer #4C[Si](C)(C)NC[C@H](O)C1=CC=C(O)C(O)=C12034.7Semi standard non polar33892256
Norepinephrine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H](CN)O[Si](C)(C)C)C=C1O1861.9Semi standard non polar33892256
Norepinephrine,2TMS,isomer #2C[Si](C)(C)OC1=CC([C@H](CN)O[Si](C)(C)C)=CC=C1O1849.1Semi standard non polar33892256
Norepinephrine,2TMS,isomer #3C[Si](C)(C)NC[C@H](O[Si](C)(C)C)C1=CC=C(O)C(O)=C11959.1Semi standard non polar33892256
Norepinephrine,2TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@@H](O)CN)C=C1O[Si](C)(C)C1897.4Semi standard non polar33892256
Norepinephrine,2TMS,isomer #5C[Si](C)(C)NC[C@H](O)C1=CC=C(O)C(O[Si](C)(C)C)=C11920.1Semi standard non polar33892256
Norepinephrine,2TMS,isomer #6C[Si](C)(C)NC[C@H](O)C1=CC=C(O[Si](C)(C)C)C(O)=C11950.9Semi standard non polar33892256
Norepinephrine,2TMS,isomer #7C[Si](C)(C)N(C[C@H](O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C2151.3Semi standard non polar33892256
Norepinephrine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H](CN)O[Si](C)(C)C)C=C1O[Si](C)(C)C1890.2Semi standard non polar33892256
Norepinephrine,3TMS,isomer #2C[Si](C)(C)NC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C11906.9Semi standard non polar33892256
Norepinephrine,3TMS,isomer #3C[Si](C)(C)NC[C@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C11895.1Semi standard non polar33892256
Norepinephrine,3TMS,isomer #4C[Si](C)(C)O[C@@H](CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=C(O)C(O)=C12146.3Semi standard non polar33892256
Norepinephrine,3TMS,isomer #5C[Si](C)(C)NC[C@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11949.6Semi standard non polar33892256
Norepinephrine,3TMS,isomer #6C[Si](C)(C)OC1=CC([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O2104.7Semi standard non polar33892256
Norepinephrine,3TMS,isomer #7C[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)C=C1O2135.1Semi standard non polar33892256
Norepinephrine,4TMS,isomer #1C[Si](C)(C)NC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11943.9Semi standard non polar33892256
Norepinephrine,4TMS,isomer #1C[Si](C)(C)NC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11989.8Standard non polar33892256
Norepinephrine,4TMS,isomer #1C[Si](C)(C)NC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11953.7Standard polar33892256
Norepinephrine,4TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1O2161.8Semi standard non polar33892256
Norepinephrine,4TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1O2148.6Standard non polar33892256
Norepinephrine,4TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1O2061.0Standard polar33892256
Norepinephrine,4TMS,isomer #3C[Si](C)(C)OC1=CC([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O2151.4Semi standard non polar33892256
Norepinephrine,4TMS,isomer #3C[Si](C)(C)OC1=CC([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O2162.6Standard non polar33892256
Norepinephrine,4TMS,isomer #3C[Si](C)(C)OC1=CC([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O2108.0Standard polar33892256
Norepinephrine,4TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2133.6Semi standard non polar33892256
Norepinephrine,4TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2129.4Standard non polar33892256
Norepinephrine,4TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2161.1Standard polar33892256
Norepinephrine,5TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1O[Si](C)(C)C2240.1Semi standard non polar33892256
Norepinephrine,5TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1O[Si](C)(C)C2101.6Standard non polar33892256
Norepinephrine,5TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1O[Si](C)(C)C1966.1Standard polar33892256
Norepinephrine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H](CN)C1=CC=C(O)C(O)=C12174.7Semi standard non polar33892256
Norepinephrine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC([C@@H](O)CN)=CC=C1O2128.4Semi standard non polar33892256
Norepinephrine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN)C=C1O2145.1Semi standard non polar33892256
Norepinephrine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC[C@H](O)C1=CC=C(O)C(O)=C12262.7Semi standard non polar33892256
Norepinephrine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN)O[Si](C)(C)C(C)(C)C)C=C1O2357.5Semi standard non polar33892256
Norepinephrine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC([C@H](CN)O[Si](C)(C)C(C)(C)C)=CC=C1O2344.2Semi standard non polar33892256
Norepinephrine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12454.1Semi standard non polar33892256
Norepinephrine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN)C=C1O[Si](C)(C)C(C)(C)C2388.8Semi standard non polar33892256
Norepinephrine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC[C@H](O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12431.6Semi standard non polar33892256
Norepinephrine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12464.7Semi standard non polar33892256
Norepinephrine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C[C@H](O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C2565.3Semi standard non polar33892256
Norepinephrine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2552.2Semi standard non polar33892256
Norepinephrine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12615.7Semi standard non polar33892256
Norepinephrine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12618.3Semi standard non polar33892256
Norepinephrine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12786.9Semi standard non polar33892256
Norepinephrine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12673.8Semi standard non polar33892256
Norepinephrine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC([C@@H](O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2795.7Semi standard non polar33892256
Norepinephrine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O2829.6Semi standard non polar33892256
Norepinephrine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12818.3Semi standard non polar33892256
Norepinephrine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12742.2Standard non polar33892256
Norepinephrine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12458.6Standard polar33892256
Norepinephrine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O3033.0Semi standard non polar33892256
Norepinephrine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O2890.0Standard non polar33892256
Norepinephrine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O2484.8Standard polar33892256
Norepinephrine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC([C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O3030.1Semi standard non polar33892256
Norepinephrine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC([C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O2917.4Standard non polar33892256
Norepinephrine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC([C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O2520.1Standard polar33892256
Norepinephrine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3062.5Semi standard non polar33892256
Norepinephrine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2887.2Standard non polar33892256
Norepinephrine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2564.4Standard polar33892256
Norepinephrine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3271.8Semi standard non polar33892256
Norepinephrine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2984.6Standard non polar33892256
Norepinephrine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2514.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Norepinephrine GC-MS (5 TMS)splash10-00di-1900000000-c9b4a0a230d610dd0e612014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Norepinephrine EI-B (Non-derivatized)splash10-000l-4900000000-b0893c23c186c5f8a3442017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Norepinephrine GC-MS (Non-derivatized)splash10-00di-1900000000-c9b4a0a230d610dd0e612017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-7900000000-ce77a851a3951304f4d02017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (3 TMS) - 70eV, Positivesplash10-0229-5974000000-c3ce7fc56442d79ae5b92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norepinephrine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0udi-0900000000-5610e21bd478a4ca7bde2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0a6r-5900000000-5d7cd24a6af23a36af3a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-004i-9000000000-3c8de1511861fa1d028c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine EI-B (HITACHI M-80) , Positive-QTOFsplash10-000l-4900000000-b0893c23c186c5f8a3442012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0udi-0900000000-11725b1d61843966aa7c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0udi-1900000000-6931e73a397f3917ad962012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0a4i-3900000000-bddd6ee748aa9ebecb152012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-056r-9500000000-6abd3337785c1b5806682012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-004i-9100000000-ede02e0e3e74bdddc9f42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOFsplash10-0udi-0900000000-11725b1d61843966aa7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOFsplash10-0udi-1900000000-6931e73a397f3917ad962017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOFsplash10-0a4i-3900000000-918c4cbdffc5e02eafd52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOFsplash10-056r-9500000000-6abd3337785c1b5806682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOFsplash10-004i-9100000000-ede02e0e3e74bdddc9f42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine 40V, Positive-QTOFsplash10-0pdi-9200000000-3d99ed9123eec62ff62d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine 30V, Positive-QTOFsplash10-0a6r-9800000000-de86d31e5e71d67974832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine 40V, Positive-QTOFsplash10-004i-9000000000-f80ee469d3be93674e922021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine 10V, Positive-QTOFsplash10-0udi-4900000000-fcf1ba1ad34b038d9ecd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norepinephrine 20V, Positive-QTOFsplash10-0a4i-9700000000-a7986bc2f2986d323df12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norepinephrine 10V, Positive-QTOFsplash10-0uk9-0900000000-3d6d08077184bc7a41e22017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norepinephrine 20V, Positive-QTOFsplash10-0f79-0900000000-470ddb022c86b9ee2fdc2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norepinephrine 40V, Positive-QTOFsplash10-0zgr-7900000000-c1bd5e2d31685ca3b0c12017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norepinephrine 10V, Negative-QTOFsplash10-014i-0900000000-9eabcf1f0c800fc62a372017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norepinephrine 20V, Negative-QTOFsplash10-0gi9-0900000000-2ff1cb280b5fe52546892017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norepinephrine 40V, Negative-QTOFsplash10-0a4i-4900000000-c16efed37585b9aac58a2017-06-28Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Heart
  • Intestine
  • Kidney
  • Leukocyte
  • Neuron
  • Ovary
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0070 (0.0034-0.011) uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0016 +/- 0.00012 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00165 +/- 0.001 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.001 +/- 0.0004 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00112 +/- 0.00006506 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0001 +/- 0.00002 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0014 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.02 (0.0096-0.031) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.047 +/- 0.0050 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.06 (0.002-0.371) umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified0.0185 (0.00342-0.0336) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0236-0.171 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.0138 (0.0062-0.032) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.000150 uMAdult (>18 years old)Not SpecifiedDopamine Beta-Hydroxylase Deficiency details
BloodDetected and Quantified0.001 +/- 0.0013 uMAdult (>18 years old)BothHeat stress details
BloodDetected and Quantified0.004 +/- 0.022 uMAdult (>18 years old)BothPheochromocytoma details
BloodDetected and Quantified0.012 +/- 0.005 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified0.0037 +/- 0.00048 uMAdult (>18 years old)BothSubarachnoid hemorrhage details
BloodDetected and Quantified0.00077 +/- 0.00129 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
BloodDetected and Quantified0.00093 +/- 0.00158 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 Quantified0.00050 +/- 0.00061 uMAdult (>18 years old)Both
Methamphetamine (MAP) psychosis
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00005 (0.00003-0.00007) uMAdult (>18 years old)BothHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00141 +/- 0.00008872 uMAdult (>18 years old)Not Specifiedborderline hypertensives details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000757 +/- 0.000266 uMAdult (>18 years old)Not SpecifiedCerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00101 uMAdult (>18 years old)Not SpecifiedCerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value but renal insufficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00108 uMAdult (>18 years old)Not SpecifiedHaemorrhagic infarction details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00432 uMAdult (>18 years old)Not SpecifiedBacterial meningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00214 uMAdult (>18 years old)Not SpecifiedLeucemic meningiosa details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000745 uMAdult (>18 years old)Not SpecifiedEncephalitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0001 +/- 0.00002 uMAdult (>18 years old)BothHypothyroidism details
UrineDetected and Quantified0.084 +/- 0.0068 umol/mmol creatinineAdult (>18 years old)BothExercise details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothSchizophrenia details
UrineDetected and Quantified0.00591 umol/mmol creatinineAdolescent (13-18 years old)FemaleDopamine-serotonin Vesicular Transport Defect details
Associated Disorders and Diseases
Disease References
Subarachnoid hemorrhage
  1. Lambert G, Naredi S, Eden E, Rydenhag B, Friberg P: Monoamine metabolism and sympathetic nervous activation following subarachnoid haemorrhage: influence of gender and hydrocephalus. Brain Res Bull. 2002 May;58(1):77-82. [PubMed:12121816 ]
Heat stress
  1. McMorris T, Swain J, Smith M, Corbett J, Delves S, Sale C, Harris RC, Potter J: Heat stress, plasma concentrations of adrenaline, noradrenaline, 5-hydroxytryptamine and cortisol, mood state and cognitive performance. Int J Psychophysiol. 2006 Aug;61(2):204-15. Epub 2005 Nov 23. [PubMed:16309771 ]
Pheochromocytoma
  1. 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 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Dopamine Beta-Hydroxylase Deficiency
  1. GeneReviews: Dopamine Beta-Hydroxylase Deficiency [Link]
Methamphetamine (MAP) 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 ]
Hypothyroidism
  1. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
Cerebral infarction
  1. Ratge D, Bauersfeld W, Wisser H: The relationship of free and conjugated catecholamines in plasma and cerebrospinal fluid in cerebral and meningeal disease. J Neural Transm. 1985;62(3-4):267-84. [PubMed:4031843 ]
Bacterial meningitis
  1. Ratge D, Bauersfeld W, Wisser H: The relationship of free and conjugated catecholamines in plasma and cerebrospinal fluid in cerebral and meningeal disease. J Neural Transm. 1985;62(3-4):267-84. [PubMed:4031843 ]
Encephalitis
  1. Ratge D, Bauersfeld W, Wisser H: The relationship of free and conjugated catecholamines in plasma and cerebrospinal fluid in cerebral and meningeal disease. J Neural Transm. 1985;62(3-4):267-84. [PubMed:4031843 ]
Schizophrenia
  1. Fryar-Williams S, Strobel JE: Biomarkers of a five-domain translational substrate for schizophrenia and schizoaffective psychosis. Biomark Res. 2015 Feb 6;3:3. doi: 10.1186/s40364-015-0028-1. eCollection 2015. [PubMed:25729574 ]
Dopamine-serotonin Vesicular Transport Defect
  1. Rilstone JJ, Alkhater RA, Minassian BA: Brain dopamine-serotonin vesicular transport disease and its treatment. N Engl J Med. 2013 Feb 7;368(6):543-50. doi: 10.1056/NEJMoa1207281. Epub 2013 Jan 30. [PubMed:23363473 ]
Associated OMIM IDs
DrugBank IDDB00368
Phenol Explorer Compound IDNot Available
FooDB IDFDB016812
KNApSAcK IDC00001424
Chemspider ID388394
KEGG Compound IDC00547
BioCyc IDNot Available
BiGG ID35313
Wikipedia LinkNorepinephrine
METLIN ID5226
PubChem Compound439260
PDB IDNot Available
ChEBI ID18357
Food Biomarker OntologyNot Available
VMH IDNRPPHR
MarkerDB IDMDB00000103
Good Scents IDNot Available
References
Synthesis ReferenceGoodall, McC.; Kirshner, Norman. Biosynthesis of adrenaline and norepinephrine by sympathetic nerves and ganglia. Circulation (1958), 17 366-71.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
  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. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
  4. Panholzer TJ, Beyer J, Lichtwald K: Coupled-column liquid chromatographic analysis of catecholamines, serotonin, and metabolites in human urine. Clin Chem. 1999 Feb;45(2):262-8. [PubMed:9931050 ]
  5. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
  6. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [PubMed:8884658 ]
  7. Kaya M, Moriwaki Y, Ka T, Inokuchi T, Yamamoto A, Takahashi S, Tsutsumi Z, Tsuzita J, Oku Y, Yamamoto T: Plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine) and oxypurinol after rigorous exercise. Metabolism. 2006 Jan;55(1):103-7. [PubMed:16324927 ]
  8. Ahlskog JE, Uitti RJ, Tyce GM, O'Brien JF, Petersen RC, Kokmen E: Plasma catechols and monoamine oxidase metabolites in untreated Parkinson's and Alzheimer's diseases. J Neurol Sci. 1996 Mar;136(1-2):162-8. [PubMed:8815165 ]
  9. Rajda C, Bencsik K, Fuvesi J, Seres E, Vecsei L, Bergquist J: The norepinephrine level is decreased in the lymphocytes of long-term interferon-beta-treated multiple sclerosis patients. Mult Scler. 2006 Jun;12(3):265-70. [PubMed:16764338 ]
  10. Takahashi S, Gjessing LR: A fluorometric method combined with thin layer chromatography for the determination of norepinephrine, epinephrine and dopamine in human urine. Clin Chim Acta. 1972 Feb;36(2):369-78. [PubMed:5008799 ]
  11. Ross HA, van Gurp PJ, Willemsen JJ, Lenders JW, Tack CJ, Sweep FC: Transport within the interstitial space, rather than membrane permeability, determines norepinephrine recovery in microdialysis. J Pharmacol Exp Ther. 2006 Nov;319(2):840-6. Epub 2006 Aug 10. [PubMed:16902052 ]
  12. Martinsons A, Rudzite V, Bratslavska O, Saulite V: The influence of kynurenine, neopterin, and norepinephrine on tubular epithelial cells and alveolar fibroblasts. Adv Exp Med Biol. 1999;467:347-52. [PubMed:10721076 ]
  13. Lake CR, Sternberg DE, van Kammen DP, Ballenger JC, Ziegler MG, Post RM, Kopin IJ, Bunney WE: Schizophrenia: elevated cerebrospinal fluid norepinephrine. Science. 1980 Jan 18;207(4428):331-3. [PubMed:7350667 ]
  14. Fernqvist E, Linde B: Potent mental stress and insulin absorption in normal subjects. Diabetes Care. 1988 Sep;11(8):650-5. [PubMed:3065003 ]
  15. Pasternak K, Dabrowski W, Wyciszczok T, Korycinska A, Dobija J, Biernacka J, Rzecki Z: The relationship between magnesium, epinephrine and norepinephrine blood concentrations during CABG with normovolemic hemodilution. Magnes Res. 2005 Dec;18(4):245-52. [PubMed:16548139 ]
  16. Albanese J, Leone M, Garnier F, Bourgoin A, Antonini F, Martin C: Renal effects of norepinephrine in septic and nonseptic patients. Chest. 2004 Aug;126(2):534-9. [PubMed:15302741 ]
  17. Shibahara J, Goto A, Niki T, Tanaka M, Nakajima J, Fukayama M: Primary pulmonary paraganglioma: report of a functioning case with immunohistochemical and ultrastructural study. Am J Surg Pathol. 2004 Jun;28(6):825-9. [PubMed:15166677 ]
  18. Wanner A, Horvath G, Brieva JL, Kumar SD, Mendes ES: Nongenomic actions of glucocorticosteroids on the airway vasculature in asthma. Proc Am Thorac Soc. 2004;1(3):235-8. [PubMed:16113440 ]
  19. Zhu Y, Zhang W, Chen M, Liu N, Guo J: [Study on expression of norepinephrine and dopamine placental tissues of normal pregnancy and pregnancy induced hypertension syndrome]. Zhonghua Fu Chan Ke Za Zhi. 2002 Mar;37(3):142-5. [PubMed:11953080 ]
  20. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  21. Mezzelani A, Landini M, Facchiano F, Raggi ME, Villa L, Molteni M, De Santis B, Brera C, Caroli AM, Milanesi L, Marabotti A: Environment, dysbiosis, immunity and sex-specific susceptibility: a translational hypothesis for regressive autism pathogenesis. Nutr Neurosci. 2015 May;18(4):145-61. doi: 10.1179/1476830513Y.0000000108. Epub 2014 Jan 21. [PubMed:24621061 ]
  22. (). Pastuszak I, Drake R, Elbein AD. Kidney N-acetylgalactosamine (GalNAc)-1-phosphate kinase, a new pathway of GalNAc activation. J Biol Chem. 1996 Aug 23;271(34):20776-82.. .
  23. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Only showing the first 10 proteins. There are 26 proteins in total.

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
Norepinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + 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
Norepinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in monooxygenase activity
Specific function:
Conversion of dopamine to noradrenaline.
Gene Name:
DBH
Uniprot ID:
P09172
Molecular weight:
69064.45
Reactions
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Waterdetails
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Waterdetails
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
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Molecular weight:
51861.565
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Martinez A, Andersson KK, Haavik J, Flatmark T: EPR and 1H-NMR spectroscopic studies on the paramagnetic iron at the active site of phenylalanine hydroxylase and its interaction with substrates and inhibitors. Eur J Biochem. 1991 Jun 15;198(3):675-82. [PubMed:1646718 ]
  4. Martinez A, Haavik J, Flatmark T: Cooperative homotropic interaction of L-noradrenaline with the catalytic site of phenylalanine 4-monooxygenase. Eur J Biochem. 1990 Oct 5;193(1):211-9. [PubMed:2226440 ]
  5. Molinoff PB: The regulation of the noradrenergic neuron. J Psychiatr Res. 1974;11:339-45. [PubMed:4156788 ]
General function:
Involved in methyltransferase activity
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P11086
Molecular weight:
30854.745
Reactions
S-Adenosylmethionine + Norepinephrine → S-Adenosylhomocysteine + Epinephrinedetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Key enzyme in the regulation of glycerol uptake and metabolism.
Gene Name:
GK
Uniprot ID:
P32189
Molecular weight:
57488.675
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Nyronen T, Pihlavisto M, Peltonen JM, Hoffren AM, Varis M, Salminen T, Wurster S, Marjamaki A, Kanerva L, Katainen E, Laaksonen L, Savola JM, Scheinin M, Johnson MS: Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine. Mol Pharmacol. 2001 May;59(5):1343-54. [PubMed:11306720 ]
  4. MacLennan SJ, Reynen PH, Martin RS, Eglen RM, Martin GR: Characterization of human recombinant alpha(2A)-adrenoceptors expressed in Chinese hamster lung cells using extracellular acidification rate changes. Br J Pharmacol. 2000 Apr;129(7):1333-8. [PubMed:10742288 ]
  5. Hieble JP, Hehr A, Li YO, Ruffolo RR Jr: Molecular basis for the stereoselective interactions of catecholamines with alpha-adrenoceptors. Proc West Pharmacol Soc. 1998;41:225-8. [PubMed:9836297 ]
  6. Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [PubMed:1980236 ]
  7. Giovannoni MP, Ghelardini C, Vergelli C, Dal Piaz V: Alpha2-agonists as analgesic agents. Med Res Rev. 2009 Mar;29(2):339-68. doi: 10.1002/med.20134. [PubMed:18680204 ]
  8. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Gobbi M, Frittoli E, Mennini T: The modulation of [3H]noradrenaline and [3H]serotonin release from rat brain synaptosomes is not mediated by the alpha 2B-adrenoceptor subtype. Naunyn Schmiedebergs Arch Pharmacol. 1990 Oct;342(4):382-6. [PubMed:1979424 ]
  4. Vizi ES, Katona I, Freund TF: Evidence for presynaptic cannabinoid CB(1) receptor-mediated inhibition of noradrenaline release in the guinea pig lung. Eur J Pharmacol. 2001 Nov 16;431(2):237-44. [PubMed:11728431 ]
  5. Rudling JE, Richardson J, Evans PD: A comparison of agonist-specific coupling of cloned human alpha(2)-adrenoceptor subtypes. Br J Pharmacol. 2000 Nov;131(5):933-41. [PubMed:11053214 ]
  6. Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [PubMed:1980236 ]
  7. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
References
  1. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]
  2. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528 ]
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
References
  1. Habecker BA, Willison BD, Shi X, Woodward WR: Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51. Epub 2006 Mar 29. [PubMed:16573647 ]
  2. Bonisch H, Bruss M: The norepinephrine transporter in physiology and disease. Handb Exp Pharmacol. 2006;(175):485-524. [PubMed:16722247 ]
  3. Mandela P, Ordway GA: KCl stimulation increases norepinephrine transporter function in PC12 cells. J Neurochem. 2006 Sep;98(5):1521-30. Epub 2006 Jul 31. [PubMed:16879714 ]
  4. Gutman DA, Owens MJ: Serotonin and norepinephrine transporter binding profile of SSRIs. Essent Psychopharmacol. 2006;7(1):35-41. [PubMed:16989291 ]
  5. Ksiazek P, Buraczynska K, Buraczynska M: Norepinephrine transporter gene (NET) polymorphism in patients with type 2 diabetes. Kidney Blood Press Res. 2006;29(6):338-43. Epub 2006 Nov 23. [PubMed:17124432 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
References
  1. Busch AE, Quester S, Ulzheimer JC, Gorboulev V, Akhoundova A, Waldegger S, Lang F, Koepsell H: Monoamine neurotransmitter transport mediated by the polyspecific cation transporter rOCT1. FEBS Lett. 1996 Oct 21;395(2-3):153-6. [PubMed:8898084 ]
  2. Breidert T, Spitzenberger F, Grundemann D, Schomig E: Catecholamine transport by the organic cation transporter type 1 (OCT1). Br J Pharmacol. 1998 Sep;125(1):218-24. [PubMed:9776363 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular weight:
62564.0
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
  2. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]
  3. Busch AE, Karbach U, Miska D, Gorboulev V, Akhoundova A, Volk C, Arndt P, Ulzheimer JC, Sonders MS, Baumann C, Waldegger S, Lang F, Koepsell H: Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52. [PubMed:9687576 ]
  4. Grundemann D, Koster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermuller N, Schomig E: Transport of monoamine transmitters by the organic cation transporter type 2, OCT2. J Biol Chem. 1998 Nov 20;273(47):30915-20. [PubMed:9812985 ]
General function:
Involved in transmembrane transport
Specific function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular weight:
61279.5
References
  1. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]
  2. Grundemann D, Schechinger B, Rappold GA, Schomig E: Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51. [PubMed:10196521 ]

Only showing the first 10 proteins. There are 26 proteins in total.