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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (21)transporters (5) Show 26 proteins XML

enzymes (21)transporters (5) Show 26 proteins

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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:37 UTC

HMDB ID

HMDB0000216

Secondary Accession Numbers

HMDB00216
HMDB0037685
HMDB37685

Metabolite Identification

Common Name

Norepinephrine

Description

Norepinephrine 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 17-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.7878665.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.1208664.386   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.7878666.698   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0    8668.4578665.156   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0    8660.4458665.156   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.4458662.073   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8664.4488664.386   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.1158665.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.7818664.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.7818662.846   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.1158662.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.4488662.846   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5    9                                                            
CONECT    6   10                                                            
CONECT    7    8   12    1                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10    5                                                  
CONECT   10    9   11    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Arterenol	ChEBI
(-)-Noradrenaline	ChEBI
(-)-Norepinephrine	ChEBI
(R)-(-)-Norepinephrine	ChEBI
(R)-4-(2-amino-1-Hydroxyethyl)-1,2-benzenediol	ChEBI
(R)-Norepinephrine	ChEBI
4-[(1R)-2-amino-1-Hydroxyethyl]-1,2-benzenediol	ChEBI
Arterenol	ChEBI
L-Noradrenaline	ChEBI
L-Norepinephrine	ChEBI
Noradrenaline	ChEBI
Norepinefrina	ChEBI
Norepinephrinum	ChEBI
(-)-(R)-Norepinephrine	HMDB
(-)-alpha-(Aminomethyl)protocatechuyl alcohol	HMDB
(R)-Noradrenaline	HMDB
4-(2-amino-1-Hydroxyethyl)-1,2-benzenediol	HMDB
Adrenor	HMDB
Aktamin	HMDB
L-2-amino-1-(3,4-Dihydroxyphenyl)ethanol	HMDB
L-3,4-Dihydroxyphenylethanolamine	HMDB
L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol	HMDB
L-Arterenol	HMDB
Levarterenol	HMDB, MeSH
Levoarterenol	HMDB
Levonor	HMDB, MeSH
Levonoradrenaline	HMDB
Levonorepinephrine	HMDB, MeSH
Levophed	HMDB, MeSH
Nor-epirenan	HMDB
Noradrenalin	HMDB
Norartrinal	HMDB
Norepirenamine	HMDB
Sympathin E	HMDB

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 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

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

noradrenaline (CHEBI:18357 )
Biogenic amines (C00547 )
Adrenalines (C00547 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	131.987	30932474
[M-H]-	Not Available	133.7	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000287

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.5 g/L	ALOGPS
logP	-0.68	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	8.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.46 m³·mol⁻¹	ChemAxon
Polarizability	16.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.031	31661259
DarkChem	[M-H]-	134.395	31661259
AllCCS	[M+H]+	138.131	32859911
AllCCS	[M-H]-	134.928	32859911
DeepCCS	[M+H]+	140.386	30932474
DeepCCS	[M-H]-	137.99	30932474
DeepCCS	[M-2H]-	173.071	30932474
DeepCCS	[M+Na]+	147.789	30932474
AllCCS	[M+H]+	138.1	32859911
AllCCS	[M+H-H2O]+	133.8	32859911
AllCCS	[M+NH4]+	142.1	32859911
AllCCS	[M+Na]+	143.3	32859911
AllCCS	[M-H]-	134.9	32859911
AllCCS	[M+Na-2H]-	136.1	32859911
AllCCS	[M+HCOO]-	137.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norepinephrine	NC[C@H](O)C1=CC(O)=C(O)C=C1	3054.2	Standard polar	33892256
Norepinephrine	NC[C@H](O)C1=CC(O)=C(O)C=C1	2138.8	Standard non polar	33892256
Norepinephrine	NC[C@H](O)C1=CC(O)=C(O)C=C1	1905.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norepinephrine,1TMS,isomer #1	C[Si](C)(C)O[C@@H](CN)C1=CC=C(O)C(O)=C1	1947.9	Semi standard non polar	33892256
Norepinephrine,1TMS,isomer #2	C[Si](C)(C)OC1=CC([C@@H](O)CN)=CC=C1O	1892.5	Semi standard non polar	33892256
Norepinephrine,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C([C@@H](O)CN)C=C1O	1900.6	Semi standard non polar	33892256
Norepinephrine,1TMS,isomer #4	C[Si](C)(C)NC[C@H](O)C1=CC=C(O)C(O)=C1	2034.7	Semi standard non polar	33892256
Norepinephrine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@H](CN)O[Si](C)(C)C)C=C1O	1861.9	Semi standard non polar	33892256
Norepinephrine,2TMS,isomer #2	C[Si](C)(C)OC1=CC([C@H](CN)O[Si](C)(C)C)=CC=C1O	1849.1	Semi standard non polar	33892256
Norepinephrine,2TMS,isomer #3	C[Si](C)(C)NC[C@H](O[Si](C)(C)C)C1=CC=C(O)C(O)=C1	1959.1	Semi standard non polar	33892256
Norepinephrine,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@@H](O)CN)C=C1O[Si](C)(C)C	1897.4	Semi standard non polar	33892256
Norepinephrine,2TMS,isomer #5	C[Si](C)(C)NC[C@H](O)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1920.1	Semi standard non polar	33892256
Norepinephrine,2TMS,isomer #6	C[Si](C)(C)NC[C@H](O)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1950.9	Semi standard non polar	33892256
Norepinephrine,2TMS,isomer #7	C[Si](C)(C)N(C[C@H](O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C	2151.3	Semi standard non polar	33892256
Norepinephrine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@H](CN)O[Si](C)(C)C)C=C1O[Si](C)(C)C	1890.2	Semi standard non polar	33892256
Norepinephrine,3TMS,isomer #2	C[Si](C)(C)NC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1906.9	Semi standard non polar	33892256
Norepinephrine,3TMS,isomer #3	C[Si](C)(C)NC[C@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1895.1	Semi standard non polar	33892256
Norepinephrine,3TMS,isomer #4	C[Si](C)(C)O[C@@H](CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=C(O)C(O)=C1	2146.3	Semi standard non polar	33892256
Norepinephrine,3TMS,isomer #5	C[Si](C)(C)NC[C@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1949.6	Semi standard non polar	33892256
Norepinephrine,3TMS,isomer #6	C[Si](C)(C)OC1=CC([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2104.7	Semi standard non polar	33892256
Norepinephrine,3TMS,isomer #7	C[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)C=C1O	2135.1	Semi standard non polar	33892256
Norepinephrine,4TMS,isomer #1	C[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)=C1	1943.9	Semi standard non polar	33892256
Norepinephrine,4TMS,isomer #1	C[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)=C1	1989.8	Standard non polar	33892256
Norepinephrine,4TMS,isomer #1	C[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)=C1	1953.7	Standard polar	33892256
Norepinephrine,4TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1O	2161.8	Semi standard non polar	33892256
Norepinephrine,4TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1O	2148.6	Standard non polar	33892256
Norepinephrine,4TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1O	2061.0	Standard polar	33892256
Norepinephrine,4TMS,isomer #3	C[Si](C)(C)OC1=CC([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	2151.4	Semi standard non polar	33892256
Norepinephrine,4TMS,isomer #3	C[Si](C)(C)OC1=CC([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	2162.6	Standard non polar	33892256
Norepinephrine,4TMS,isomer #3	C[Si](C)(C)OC1=CC([C@H](CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	2108.0	Standard polar	33892256
Norepinephrine,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2133.6	Semi standard non polar	33892256
Norepinephrine,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2129.4	Standard non polar	33892256
Norepinephrine,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@@H](O)CN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2161.1	Standard polar	33892256
Norepinephrine,5TMS,isomer #1	C[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)C	2240.1	Semi standard non polar	33892256
Norepinephrine,5TMS,isomer #1	C[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)C	2101.6	Standard non polar	33892256
Norepinephrine,5TMS,isomer #1	C[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)C	1966.1	Standard polar	33892256
Norepinephrine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](CN)C1=CC=C(O)C(O)=C1	2174.7	Semi standard non polar	33892256
Norepinephrine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC([C@@H](O)CN)=CC=C1O	2128.4	Semi standard non polar	33892256
Norepinephrine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN)C=C1O	2145.1	Semi standard non polar	33892256
Norepinephrine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC[C@H](O)C1=CC=C(O)C(O)=C1	2262.7	Semi standard non polar	33892256
Norepinephrine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN)O[Si](C)(C)C(C)(C)C)C=C1O	2357.5	Semi standard non polar	33892256
Norepinephrine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC([C@H](CN)O[Si](C)(C)C(C)(C)C)=CC=C1O	2344.2	Semi standard non polar	33892256
Norepinephrine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1	2454.1	Semi standard non polar	33892256
Norepinephrine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN)C=C1O[Si](C)(C)C(C)(C)C	2388.8	Semi standard non polar	33892256
Norepinephrine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC[C@H](O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2431.6	Semi standard non polar	33892256
Norepinephrine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2464.7	Semi standard non polar	33892256
Norepinephrine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C[C@H](O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	2565.3	Semi standard non polar	33892256
Norepinephrine,3TBDMS,isomer #1	CC(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)C	2552.2	Semi standard non polar	33892256
Norepinephrine,3TBDMS,isomer #2	CC(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)=C1	2615.7	Semi standard non polar	33892256
Norepinephrine,3TBDMS,isomer #3	CC(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)=C1	2618.3	Semi standard non polar	33892256
Norepinephrine,3TBDMS,isomer #4	CC(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)=C1	2786.9	Semi standard non polar	33892256
Norepinephrine,3TBDMS,isomer #5	CC(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)=C1	2673.8	Semi standard non polar	33892256
Norepinephrine,3TBDMS,isomer #6	CC(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=C1O	2795.7	Semi standard non polar	33892256
Norepinephrine,3TBDMS,isomer #7	CC(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	2829.6	Semi standard non polar	33892256
Norepinephrine,4TBDMS,isomer #1	CC(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)=C1	2818.3	Semi standard non polar	33892256
Norepinephrine,4TBDMS,isomer #1	CC(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)=C1	2742.2	Standard non polar	33892256
Norepinephrine,4TBDMS,isomer #1	CC(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)=C1	2458.6	Standard polar	33892256
Norepinephrine,4TBDMS,isomer #2	CC(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	3033.0	Semi standard non polar	33892256
Norepinephrine,4TBDMS,isomer #2	CC(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	2890.0	Standard non polar	33892256
Norepinephrine,4TBDMS,isomer #2	CC(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	2484.8	Standard polar	33892256
Norepinephrine,4TBDMS,isomer #3	CC(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=C1O	3030.1	Semi standard non polar	33892256
Norepinephrine,4TBDMS,isomer #3	CC(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=C1O	2917.4	Standard non polar	33892256
Norepinephrine,4TBDMS,isomer #3	CC(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=C1O	2520.1	Standard polar	33892256
Norepinephrine,4TBDMS,isomer #4	CC(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)C	3062.5	Semi standard non polar	33892256
Norepinephrine,4TBDMS,isomer #4	CC(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)C	2887.2	Standard non polar	33892256
Norepinephrine,4TBDMS,isomer #4	CC(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)C	2564.4	Standard polar	33892256
Norepinephrine,5TBDMS,isomer #1	CC(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)C	3271.8	Semi standard non polar	33892256
Norepinephrine,5TBDMS,isomer #1	CC(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)C	2984.6	Standard non polar	33892256
Norepinephrine,5TBDMS,isomer #1	CC(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)C	2514.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Norepinephrine GC-MS (5 TMS)	splash10-00di-1900000000-c9b4a0a230d610dd0e61	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Norepinephrine EI-B (Non-derivatized)	splash10-000l-4900000000-b0893c23c186c5f8a344	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Norepinephrine GC-MS (Non-derivatized)	splash10-00di-1900000000-c9b4a0a230d610dd0e61	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-7900000000-ce77a851a3951304f4d0	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (3 TMS) - 70eV, Positive	splash10-0229-5974000000-c3ce7fc56442d79ae5b9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norepinephrine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0udi-0900000000-5610e21bd478a4ca7bde	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0a6r-5900000000-5d7cd24a6af23a36af3a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-004i-9000000000-3c8de1511861fa1d028c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine EI-B (HITACHI M-80) , Positive-QTOF	splash10-000l-4900000000-b0893c23c186c5f8a344	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0udi-0900000000-11725b1d61843966aa7c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0udi-1900000000-6931e73a397f3917ad96	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0a4i-3900000000-bddd6ee748aa9ebecb15	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-056r-9500000000-6abd3337785c1b580668	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-004i-9100000000-ede02e0e3e74bdddc9f4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOF	splash10-0udi-0900000000-11725b1d61843966aa7c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOF	splash10-0udi-1900000000-6931e73a397f3917ad96	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOF	splash10-0a4i-3900000000-918c4cbdffc5e02eafd5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOF	splash10-056r-9500000000-6abd3337785c1b580668	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine LC-ESI-QQ , positive-QTOF	splash10-004i-9100000000-ede02e0e3e74bdddc9f4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine 40V, Positive-QTOF	splash10-0pdi-9200000000-3d99ed9123eec62ff62d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine 30V, Positive-QTOF	splash10-0a6r-9800000000-de86d31e5e71d6797483	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine 40V, Positive-QTOF	splash10-004i-9000000000-f80ee469d3be93674e92	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine 10V, Positive-QTOF	splash10-0udi-4900000000-fcf1ba1ad34b038d9ecd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norepinephrine 20V, Positive-QTOF	splash10-0a4i-9700000000-a7986bc2f2986d323df1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norepinephrine 10V, Positive-QTOF	splash10-0uk9-0900000000-3d6d08077184bc7a41e2	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norepinephrine 20V, Positive-QTOF	splash10-0f79-0900000000-470ddb022c86b9ee2fdc	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norepinephrine 40V, Positive-QTOF	splash10-0zgr-7900000000-c1bd5e2d31685ca3b0c1	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norepinephrine 10V, Negative-QTOF	splash10-014i-0900000000-9eabcf1f0c800fc62a37	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norepinephrine 20V, Negative-QTOF	splash10-0gi9-0900000000-2ff1cb280b5fe5254689	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norepinephrine 40V, Negative-QTOF	splash10-0a4i-4900000000-c16efed37585b9aac58a	2017-06-28	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View 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

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Tyrosine metabolism	Not Available
Aromatic L-Aminoacid Decarboxylase Deficiency		Not Available
Tyrosine hydroxylase deficiency		Not Available
Alkaptonuria		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0070 (0.0034-0.011) uM	Adult (>18 years old)	Both	Normal	16324927	details
Blood	Detected and Quantified	0.0016 +/- 0.00012 uM	Adult (>18 years old)	Both	Normal	12121816	details
Blood	Detected and Quantified	0.00165 +/- 0.001 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.001 +/- 0.0004 uM	Adult (>18 years old)	Both	Normal	22626821	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00112 +/- 0.00006506 uM	Not Specified	Not Specified	Normal	6744640	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0001 +/- 0.00002 uM	Adult (>18 years old)	Male	Normal	8884658	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0014 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.02 (0.0096-0.031) uM	Adult (>18 years old)	Both	Normal	12834252	details
Urine	Detected and Quantified	0.047 +/- 0.0050 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	3122251	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.06 (0.002-0.371) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	21670092	details
Urine	Detected and Quantified	0.0185 (0.00342-0.0336) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9931050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25729574	details
Urine	Detected and Quantified	0.0236-0.171 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	23363473	details
Urine	Detected and Quantified	0.0138 (0.0062-0.032) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.000150 uM	Adult (>18 years old)	Not Specified	Dopamine Beta-Hydroxylase Deficiency	GeneReviews:...	details
Blood	Detected and Quantified	0.001 +/- 0.0013 uM	Adult (>18 years old)	Both	Heat stress	16309771	details
Blood	Detected and Quantified	0.004 +/- 0.022 uM	Adult (>18 years old)	Both	Pheochromocytoma	9626157	details
Blood	Detected and Quantified	0.012 +/- 0.005 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected and Quantified	0.0037 +/- 0.00048 uM	Adult (>18 years old)	Both	Subarachnoid hemorrhage	12121816	details
Blood	Detected and Quantified	0.00077 +/- 0.00129 uM	Adult (>18 years old)	Both	Methamphetamine (MAP) psychosis	8878306	details
Blood	Detected and Quantified	0.00093 +/- 0.00158 uM	Adult (>18 years old)	Both	Methamphetamine (MAP) psychosis	8878306	details
Blood	Detected and Quantified	0.00063 +/- 0.00101 uM	Adult (>18 years old)	Both	Methamphetamine (MAP) psychosis	8878306	details
Blood	Detected and Quantified	0.00050 +/- 0.00061 uM	Adult (>18 years old)	Both	Methamphetamine (MAP) psychosis	8878306	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00005 (0.00003-0.00007) uM	Adult (>18 years old)	Both	Hypothyroidism	9849813	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00141 +/- 0.00008872 uM	Adult (>18 years old)	Not Specified	borderline hypertensives	6744640	details
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	4031843	details
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	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00108 uM	Adult (>18 years old)	Not Specified	Haemorrhagic infarction	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00432 uM	Adult (>18 years old)	Not Specified	Bacterial meningitis	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00214 uM	Adult (>18 years old)	Not Specified	Leucemic meningiosa	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000745 uM	Adult (>18 years old)	Not Specified	Encephalitis	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0001 +/- 0.00002 uM	Adult (>18 years old)	Both	Hypothyroidism	9849813	details
Urine	Detected and Quantified	0.084 +/- 0.0068 umol/mmol creatinine	Adult (>18 years old)	Both	Exercise	3122251	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	25729574	details
Urine	Detected and Quantified	0.00591 umol/mmol creatinine	Adolescent (13-18 years old)	Female	Dopamine-serotonin Vesicular Transport Defect	23363473	details

Associated Disorders and Diseases

Disease References

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 ]
Uremia
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
GeneReviews: Dopamine Beta-Hydroxylase Deficiency [Link]
Methamphetamine (MAP) psychosis
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
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
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
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
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
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
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

105800 (Subarachnoid hemorrhage)
171300 (Pheochromocytoma)
223360 (Dopamine Beta-Hydroxylase Deficiency)
181500 (Schizophrenia)

External Links

DrugBank ID

DB00368

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18357

Food Biomarker Ontology

Not Available

VMH ID

NRPPHR

MarkerDB ID

MDB00000103

Good Scents ID

Not Available

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

Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
(). 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.. .
(). 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.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

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 peroxide	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

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 peroxide	details

Enzyme Details

3. Dopamine beta-hydroxylase

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 + Water	details
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Water	details

Enzyme Details

4. Catechol O-methyltransferase

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 + Normetanephrine	details

Enzyme Details

5. Phenylalanine-4-hydroxylase

General function:: Involved in amino acid binding
Specific function:: Not Available
Gene Name:: PAH
Uniprot ID:: P00439
Molecular weight:: 51861.565

References

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 ]
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 ]
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 ]
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 ]
Molinoff PB: The regulation of the noradrenergic neuron. J Psychiatr Res. 1974;11:339-45. [PubMed:4156788 ]

Enzyme Details

6. Phenylethanolamine N-methyltransferase

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 + Epinephrine	details

Enzyme Details

7. Glycerol kinase

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

Enzyme Details

8. Cytochrome P450 1A2

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

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 ]

Enzyme Details

9. Alpha-2A adrenergic receptor

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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]

Enzyme Details

10. Alpha-2B adrenergic receptor

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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

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

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 ]
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 ]

Enzyme Details

2. Sodium-dependent noradrenaline transporter

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

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 ]
Bonisch H, Bruss M: The norepinephrine transporter in physiology and disease. Handb Exp Pharmacol. 2006;(175):485-524. [PubMed:16722247 ]
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 ]
Gutman DA, Owens MJ: Serotonin and norepinephrine transporter binding profile of SSRIs. Essent Psychopharmacol. 2006;7(1):35-41. [PubMed:16989291 ]
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 ]

Enzyme Details

3. Solute carrier family 22 member 1

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

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 ]
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 ]

Enzyme Details

4. Solute carrier family 22 member 2

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

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 ]
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 ]
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 ]
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 ]

Enzyme Details

5. Solute carrier family 22 member 3

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

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 ]
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.

Show all enzymes and transporters

Showing metabocard for Norepinephrine (HMDB0000216)

MOL for HMDB0000216 (Norepinephrine)

3D MOL for HMDB0000216 (Norepinephrine)

3D SDF for HMDB0000216 (Norepinephrine)

3D-SDF for HMDB0000216 (Norepinephrine)

PDB for HMDB0000216 (Norepinephrine)

3D PDB for HMDB0000216 (Norepinephrine)

SMILES for HMDB0000216 (Norepinephrine)

INCHI for HMDB0000216 (Norepinephrine)

Structure for HMDB0000216 (Norepinephrine)

3D Structure for HMDB0000216 (Norepinephrine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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References

Reactions

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Transporters

References

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References