Human Metabolome Database Version 3.5

Showing metabocard for Norepinephrine (HMDB00216)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:06 -0700
HMDB ID HMDB00216
Secondary Accession Numbers None
Metabolite Identification
Common Name Norepinephrine
Description 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.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-(R)-Norepinephrine
  2. (-)-alpha-(Aminomethyl)protocatechuyl alcohol
  3. (-)-Arterenol
  4. (-)-Noradrenaline
  5. (-)-Norepinephrine
  6. (R)-(-)-Norepinephrine
  7. (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol
  8. (R)-Noradrenaline
  9. (R)-Norepinephrine
  10. 4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol
  11. 4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol
  12. Adrenor
  13. Aktamin
  14. Arterenol
  15. L-2-Amino-1-(3,4-dihydroxyphenyl)ethanol
  16. L-3,4-Dihydroxyphenylethanolamine
  17. L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol
  18. L-Arterenol
  19. L-Noradrenaline
  20. L-Norepinephrine
  21. Levarterenol
  22. Levoarterenol
  23. Levonor
  24. Levonoradrenaline
  25. Levonorepinephrine
  26. Levophed
  27. Nor-Epirenan
  28. Noradrenalin
  29. Noradrenaline
  30. Norartrinal
  31. Norepirenamine
  32. Sympathin E
Chemical Formula C8H11NO3
Average Molecular Weight 169.1778
Monoisotopic Molecular Weight 169.073893223
IUPAC Name 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
Traditional IUPAC Name norepinephrine
CAS Registry Number 51-41-2
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 Key SFLSHLFXELFNJZ-QMMMGPOBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Benzenediols
Other Descriptors
  • Adrenalines(KEGG)
  • Aromatic Homomonocyclic Compounds
  • Biogenic amines(KEGG)
  • noradrenaline(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • 1,2 Diphenol
  • Benzyl Alcohol Derivative
  • Phenethylamine
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct Parent Catecholamines and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tyrosine metabolism
Application Not Available
Cellular locations
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 145.2 - 146.4 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 849 mg/mL Not Available
LogP -1.24 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 12.5 g/L ALOGPS
LogP -1.40 ALOGPS
LogP -0.68 ChemAxon
LogS -1.13 ALOGPS
pKa (strongest acidic) 9.5 ChemAxon
pKa (strongest basic) 8.85 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 86.71 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 44.46 ChemAxon
Polarizability 16.96 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Lymphocyte
  • Neuron
  • Pancreas
  • Placenta
  • Kidney
  • Epidermis
  • Brain
  • Prostate
  • Adrenal Gland
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Medulla
  • Nerve Cells
  • Platelet
  • Gonads
  • Heart
  • Central Nervous System
Pathways
Name SMPDB Link KEGG Link
Catecholamine Biosynthesis SMP00012 map00350 Link_out
Tyrosine Metabolism SMP00006 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0070 (0.0034-0.011) uM Adult (>18 years old) Both Comment Normal
Blood Detected and Quantified
0.0016 +/- 0.00012 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.00165 +/- 0.001 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.00112 +/- 6.506e-05 uM Not Specified Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0001 +/- 0.00002 uM Adult (>18 years old) Male Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0014 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.02 (0.0096-0.031) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.047 +/- 0.0050 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0185 (0.00342-0.0336) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0138 (0.0062-0.032) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.001 +/- 0.0013 uM Adult (>18 years old) Both Heat stress
Blood Detected and Quantified 0.004 +/- 0.022 uM Adult (>18 years old) Both Pheochromocytoma
Blood Detected and Quantified 0.0037 +/- 0.00048 uM Adult (>18 years old) Both Subarachnoid haemorrhage
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00005 (0.00003-0.00007) uM Adult (>18 years old) Both Hypothyroidism
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00141 +/- 8.872e-05 uM Adult (>18 years old) Not Specified borderline hypertensives
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000757 +/- 0.000266 uM Adult (>18 years old) Not Specified Cerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00101 uM Adult (>18 years old) Not Specified Cerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value but renal insufficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00108 uM Adult (>18 years old) Not Specified Haemorrhagic infraction
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00432 uM Adult (>18 years old) Not Specified Bacterial meningitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00214 uM Adult (>18 years old) Not Specified Leucemic meningiosa
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000745 uM Adult (>18 years old) Not Specified Encephalitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0001 +/- 0.00002 uM Adult (>18 years old) Both Hypothyroidism
Urine Detected and Quantified 0.084 +/- 0.0068 umol/mmol creatinine Adult (>18 years old) Both Exercise
Associated Disorders and Diseases
Disease References
Hypothyroidism
  • 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 Link_out
      Subarachnoid hemorrhage
      • 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 Link_out
          Heat stress
          • 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 Link_out
              Pheochromocytoma
              • 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 Link_out
                  Associated OMIM IDs
                  DrugBank ID DB00368 Link_out
                  DrugBank Metabolite ID Not Available
                  Phenol Explorer Compound ID Not Available
                  Phenol Explorer Metabolite ID Not Available
                  FoodDB ID FDB000895
                  KNApSAcK ID C00001424 Link_out
                  Chemspider ID 388394 Link_out
                  KEGG Compound ID C00547 Link_out
                  BioCyc ID NOREPINEPHRINE Link_out
                  BiGG ID 35313 Link_out
                  Wikipedia Link Norepinephrine Link_out
                  NuGOwiki Link HMDB00216 Link_out
                  Metagene Link HMDB00216 Link_out
                  METLIN ID 5226 Link_out
                  PubChem Compound 439260 Link_out
                  PDB ID LNR Link_out
                  ChEBI ID 18357 Link_out
                  References
                  Synthesis Reference Goodall, 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. 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 Link_out
                  2. 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 Link_out
                  3. 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 Link_out
                  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 Link_out
                  5. 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 Link_out
                  6. 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 Link_out
                  7. 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 Link_out
                  8. 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 Link_out
                  9. 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 Link_out
                  10. 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 Link_out
                  11. 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 Link_out
                  12. Fernqvist E, Linde B: Potent mental stress and insulin absorption in normal subjects. Diabetes Care. 1988 Sep;11(8):650-5. Pubmed: 3065003 Link_out
                  13. 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 Link_out
                  14. 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 Link_out
                  15. 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 Link_out
                  16. 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 Link_out
                  17. 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 Link_out
                  18. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. Pubmed: 6085021 Link_out
                  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 Link_out
                  20. 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.

                  Enzymes
                  Name: Amine oxidase [flavin-containing] B
                  Reactions:
                  Norepinephrine + Water + Oxygen unknown 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxide details
                  Gene Name: MAOB
                  Uniprot ID: P27338 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Amine oxidase [flavin-containing] A
                  Reactions:
                  Norepinephrine + Water + Oxygen unknown 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxide details
                  Gene Name: MAOA
                  Uniprot ID: P21397 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Dopamine beta-hydroxylase
                  Reactions:
                  Dopamine + Ascorbic acid + Oxygen unknown Norepinephrine + Dehydroascorbic acid + Water details
                  Gene Name: DBH
                  Uniprot ID: P09172 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Catechol O-methyltransferase
                  Reactions:
                  S-Adenosylmethionine + Norepinephrine unknown S-Adenosylhomocysteine + Normetanephrine details
                  Gene Name: COMT
                  Uniprot ID: P21964 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Phenylalanine-4-hydroxylase
                  Reactions: Not Available
                  Gene Name: PAH
                  Uniprot ID: P00439 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Phenylethanolamine N-methyltransferase
                  Reactions:
                  S-Adenosylmethionine + Norepinephrine unknown S-Adenosylhomocysteine + Epinephrine details
                  Gene Name: PNMT
                  Uniprot ID: P11086 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Glycerol kinase
                  Reactions: Not Available
                  Gene Name: GK
                  Uniprot ID: P32189 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Cytochrome P450 1A2
                  Reactions: Not Available
                  Gene Name: CYP1A2
                  Uniprot ID: P05177 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Alpha-2A adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRA2A
                  Uniprot ID: P08913 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Alpha-2B adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRA2B
                  Uniprot ID: P18089 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Beta-1 adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRB1
                  Uniprot ID: P08588 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Beta-2 adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRB2
                  Uniprot ID: P07550 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Alpha-1A adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRA1A
                  Uniprot ID: P35348 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Alpha-1B adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRA1B
                  Uniprot ID: P35368 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Alpha-1D adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRA1D
                  Uniprot ID: P25100 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Synaptotagmin-5
                  Reactions: Not Available
                  Gene Name: SYT5
                  Uniprot ID: O00445 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Beta-3 adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRB3
                  Uniprot ID: P13945 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Norepinephrine transporter isoform 2
                  Reactions: Not Available
                  Gene Name: Not Available
                  Uniprot ID: Q9Y6W9 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Alpha-2C adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRA2C
                  Uniprot ID: P18825 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Norepinephrine transporter isoform 1
                  Reactions: Not Available
                  Gene Name: Not Available
                  Uniprot ID: Q9UQ04 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Norepinephrine transporter
                  Reactions: Not Available
                  Gene Name: NET
                  Uniprot ID: Q71UR5 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Transporters
                  Name: Solute carrier family 22 member 5
                  Reactions: Not Available
                  Gene Name: SLC22A5
                  Uniprot ID: O76082 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Sodium-dependent noradrenaline transporter
                  Reactions: Not Available
                  Gene Name: SLC6A2
                  Uniprot ID: P23975 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Solute carrier family 22 member 1
                  Reactions: Not Available
                  Gene Name: SLC22A1
                  Uniprot ID: O15245 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Solute carrier family 22 member 2
                  Reactions: Not Available
                  Gene Name: SLC22A2
                  Uniprot ID: O15244 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Solute carrier family 22 member 3
                  Reactions: Not Available
                  Gene Name: SLC22A3
                  Uniprot ID: O75751 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA