| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (-)-(R)-Norepinephrine
- (-)-alpha-(Aminomethyl)protocatechuyl alcohol
- (-)-Arterenol
- (-)-Noradrenaline
- (-)-Norepinephrine
- (R)-(-)-Norepinephrine
- (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol
- (R)-Noradrenaline
- (R)-Norepinephrine
- 4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol
- 4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol
- Adrenor
- Aktamin
- Arterenol
- L-2-Amino-1-(3,4-dihydroxyphenyl)ethanol
- L-3,4-Dihydroxyphenylethanolamine
- L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol
- L-Arterenol
- L-Noradrenaline
- L-Norepinephrine
- Levarterenol
- Levoarterenol
- Levonor
- Levonoradrenaline
- Levonorepinephrine
- Levophed
- Nor-Epirenan
- Noradrenalin
- Noradrenaline
- Norartrinal
- Norepirenamine
- 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 |
|
| Biofunction |
- Component of Tyrosine metabolism
|
| Application |
Not Available |
| Cellular locations |
|
| 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) |
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| Predicted Properties |
|
| Spectra |
|
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| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
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| 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 |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.0070 (0.0034-0.011) uM |
Adult (>18 years old) |
Both |
Normal |
Exercise
|
| Blood |
Detected and Quantified |
|
0.0016 +/- 0.00012 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.00165 +/- 0.001 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00112 +/- 6.506e-05 uM |
Not Specified |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0001 +/- 0.00002 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0014 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.02 (0.0096-0.031) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.047 +/- 0.0050 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.0185 (0.00342-0.0336) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.0138 (0.0062-0.032) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.001 +/- 0.0013 uM |
Adult (>18 years old) |
Both |
Heat stress |
Not Available |
| Blood |
Detected and Quantified |
|
0.004 +/- 0.022 uM |
Adult (>18 years old) |
Both |
Pheochromocytoma |
Not Available |
| Blood |
Detected and Quantified |
|
0.0037 +/- 0.00048 uM |
Adult (>18 years old) |
Both |
Subarachnoid haemorrhage |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00005 (0.00003-0.00007) uM |
Adult (>18 years old) |
Both |
Hypothyroidism |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00141 +/- 8.872e-05 uM |
Adult (>18 years old) |
Not Specified |
borderline hypertensives |
Not Available |
| 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 |
Not Available |
| 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 |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00108 uM |
Adult (>18 years old) |
Not Specified |
Haemorrhagic infraction |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00432 uM |
Adult (>18 years old) |
Not Specified |
Bacterial meningitis |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00214 uM |
Adult (>18 years old) |
Not Specified |
Leucemic meningiosa |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000745 uM |
Adult (>18 years old) |
Not Specified |
Encephalitis |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0001 +/- 0.00002 uM |
Adult (>18 years old) |
Both |
Hypothyroidism |
Not Available |
| Urine |
Detected and Quantified |
|
0.084 +/- 0.0068 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Exercise |
Not Available |
|
| 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
|
| 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
|
| 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
|
| 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
|
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| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
DB00368  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB000895 |
| KNApSAcK ID |
C00001424  |
| Chemspider ID |
388394  |
| KEGG Compound ID |
C00547  |
| BioCyc ID |
NOREPINEPHRINE  |
| BiGG ID |
35313  |
| Wikipedia Link |
Norepinephrine  |
| NuGOwiki Link |
HMDB00216  |
| Metagene Link |
HMDB00216  |
| METLIN ID |
5226  |
| PubChem Compound |
439260  |
| PDB ID |
LNR  |
| ChEBI ID |
18357  |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Fernqvist E, Linde B: Potent mental stress and insulin absorption in normal subjects. Diabetes Care. 1988 Sep;11(8):650-5.
Pubmed: 3065003
- 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
- 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
- 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
- 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
- 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
- Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9.
Pubmed: 6085021
- 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
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| Enzymes |
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| Name: |
Dopamine beta-hydroxylase
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| Reactions: |
- 3,4-dihydroxyphenethylamine + ascorbate + O2 = noradrenaline + dehydroascorbate + H2O [RN:R02535]
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| Gene Name: |
DBH |
| Uniprot ID: |
P09172  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Phenylalanine-4-hydroxylase
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| Reactions: |
- L-phenylalanine + tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin [RN:R07211]
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| Gene Name: |
PAH |
| Uniprot ID: |
P00439  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Glycerol kinase
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| Reactions: |
- ATP + glycerol = ADP + sn-glycerol 3-phosphate [RN:R00847]
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| Gene Name: |
GK |
| Uniprot ID: |
P32189  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 1A2
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP1A2 |
| Uniprot ID: |
P05177  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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