Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2018-05-28 23:03:53 UTC
Primary IDFDB000895
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-Norepinephrine
DescriptionNoradrenaline (BAN) (abbreviated NA or NAd) or norepinephrine (INN) (abbreviated norepi or NE) is a catecholamine with dual roles as a hormone and a neurotransmitter.; Noradrenaline acts on both alpha-1 and alpha-2 adrenergic receptors to cause vasoconstriction. Its effect in-vitro is often limited to the increasing of blood pressure through antagonising alpha-1 and alpha-2 receptors and causing a resultant increase in systemic vascular resistance.; Norepinephrine is a catecholamine and a phenethylamine. The natural stereoisomer is L-(?)-(R)-norepinephrine. The prefix nor-, is derived from the German abbreviation for "N ohne Radikal" (N, the symbol for nitrogen, without radical), referring to the absence of the methyl functional group at the nitrogen atom.; Norepinephrine, along with dopamine, has come to be recognized as playing a large role in attention and focus. For people with ADHD, psychostimulant medications such as methylphenidate (Ritalin/Concerta), dextroamphetamine (Dexedrine), and Adderall (a mixture of dextroamphetamine and racemic amphetamine salts) are prescribed to help increase levels of norepinephrine and dopamine. Atomoxetine (Strattera) is a selective norepinephrine reuptake inhibitor, and is a unique ADHD medication, as it affects only norepinephrine, rather than dopamine. As a result, Strattera has a lower abuse potential. However, it may not be as effective as the psychostimulants are with many people who have ADHD. Consulting with a physician, physician assistant or nurse practitioner is needed to find the appropriate medication and dosage. (Other SNRIs, currently approved as antidepressants, have also been used off-label for treatment of ADHD.); 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.; ?-methyltyrosine is a substance that intervenes in norepinephrine synthesis by substituting tyrosine for tyrosine hydroxylase, and blocking this enzyme. Norepinephrine is elevated in the urine of people who consume bananas. .
CAS Number51-41-2
Structure
Thumb
Synonyms
SynonymSource
(-)-ArterenolChEBI
(-)-NoradrenalineChEBI
(-)-NorepinephrineChEBI
(R)-(-)-NorepinephrineChEBI
(R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediolChEBI
(R)-NorepinephrineChEBI
4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediolChEBI
ArterenolChEBI
L-NoradrenalineChEBI
L-NOREPINEPHRINEChEBI
NoradrenalineChEBI
NorepinefrinaChEBI
NorepinephrinumChEBI
Nor adrenalinKegg
(-)-(R)-NorepinephrineHMDB
(-)-alpha-(Aminomethyl)protocatechuyl alcoholHMDB
(R)-NoradrenalineHMDB
4-(2-Amino-1-hydroxyethyl)-1,2-benzenediolHMDB
AdrenorHMDB
AktaminHMDB
L-2-Amino-1-(3,4-dihydroxyphenyl)ethanolHMDB
L-3,4-DihydroxyphenylethanolamineHMDB
L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcoholHMDB
L-ArterenolHMDB
LevarterenolHMDB
LevoarterenolHMDB
LevonorHMDB
LevonoradrenalineHMDB
LevonorepinephrineHMDB
LevophedHMDB
Nor-epirenanHMDB
NoradrenalinHMDB
NorartrinalHMDB
NorepirenamineHMDB
Sympathin eHMDB
Hydrochloride, norepinephrineHMDB
Levophed bitartrateHMDB
Noradrénaline tartrate renaudinHMDB
Norepinephrine hydrochloride, (+)-isomerHMDB
Norepinephrine hydrochloride, (+,-)-isomerHMDB
Norepinephrine L-tartrate (1:1), monohydrateHMDB
Norepinephrine, (+,-)-isomerHMDB
Renaudin brand OF norepinephrine bitartrateHMDB
Bitartrate, noradrenalineHMDB
Noradrenaline bitartrateHMDB
Norepinephrine L-tartrate (1:1)HMDB
Norepinephrine L-tartrate (1:1), (+,-)-isomerHMDB
Norepinephrine L-tartrate (1:1), monohydrate, (+)-isomerHMDB
Abbott brand OF levophed bitartrateHMDB
Aventis brand OF norepinephrine hydrochlorideHMDB
Bitartrate, norepinephrineHMDB
Norepinephrin D-tartrate (1:1)HMDB
Norepinephrine bitartrateHMDB
Norepinephrine hydrochlorideHMDB
Norepinephrine D-tartrate (1:1)HMDB
Norepinephrine L-tartrate, (+)-isomerHMDB
Tartrate renaudin, noradrénalineHMDB
Bitartrate, levophedHMDB
Norepinephrine L-tartrate (1:2)HMDB
Norepinephrine, (+)-isomerHMDB
Renaudin, noradrénaline tartrateHMDB
(-)-(r)-norepinephrinebiospider
(-)-alpha-(aminomethyl)protocatechuyl alcoholbiospider
(-)-arterenolbiospider
(-)-noradrenalinebiospider
(-)-norepinephrinebiospider
(CF2Cl)2biospider
(r)-(-)-norepinephrinebiospider
(r)-noradrenalinebiospider
(r)-norepinephrinebiospider
[11c]norepinephrine Hydrochloridebiospider
1,1,2,2-Tetrafluoro-1,2-Dichloroethanebiospider
1,2-Benzenediol, 4-((1R)-2-amino-1-hydroxyethyl)-biospider
1,2-Benzenediol, 4-((R)-2-amino-1-hydroxyethyl)-biospider
1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)-biospider
1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)- (9CI)biospider
1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)-(-)-biospider
1,2-Benzenediol, 4-[(1R)-2-amino-1-hydroxyethyl]-biospider
1,2-Dichlorotetrafluoroethanebiospider
4-(2-amino-1-hydroxyethyl)-1,2-benzenediolbiospider
4-(2-Amino-1-hydroxyethyl)benzene-1,2-diolbiospider
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diolbiospider
51-40-1 (l-tartrate (1:1))biospider
Arcton 114biospider
Arcton 33biospider
Benzyl alcohol, alpha-(aminomethyl)-3,4-dihydroxy-, (-)-biospider
Cryofluoranbiospider
Cryofluoranebiospider
D-(-)-noradrenalinebiospider
Dichloro-1,1,2,2-tetrafluoroethanebiospider
Dichlorotetrafluoroethanebiospider
Ethane, 1,2-dichloro-1,1,2,2-tetrafluoro-biospider
Ethane, 1,2-dichlorotetrafluoro-biospider
Freon 114biospider
Frigen 114biospider
Frigidermbiospider
Genetron 114biospider
Genetron 316biospider
Halocarbon 114biospider
Halon 242biospider
Isotron 114biospider
l-1-(3,4-Dihydroxyphenyl)-2-aminoethanolbiospider
l-2-Amino-1-(3,4-dihydroxyphenyl)ethanolbiospider
l-3,4-Dihydroxyphenylethanolaminebiospider
l-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcoholbiospider
L-arterenolbiospider
L-noradrenalinebiospider
L-norepinephrinebiospider
L(-)-norepinephrine bitartratebiospider
Ledon 114biospider
Levarterenolobiospider
Levarterenolo [dcit]biospider
Nor adrenalin (TN)biospider
Noradrenalin, l-biospider
Noradrenalinabiospider
Noradrenaline (JP15)biospider
Noradrenalinumbiospider
Noreinefrinabiospider
Norepinephrinebiospider
Norepinephrine (inn)biospider
Norepinephrine [inn:jan]biospider
Norepinephrine l-Tartrate (1:1)biospider
Norepinephrine noradrenalinbiospider
Propellant 114biospider
Refrigerant 114biospider
Refrigerant R114biospider
S-dichlorotetrafluoroethanebiospider
SYM-dichlorotetrafluoroethanebiospider
Predicted Properties
PropertyValueSource
Water Solubility12.5 g/LALOGPS
logP-1.4ALOGPS
logP-0.68ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)8.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.46 m³·mol⁻¹ChemAxon
Polarizability16.96 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H11NO3
IUPAC name4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
InChI IdentifierInChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2
InChI KeySFLSHLFXELFNJZ-UHFFFAOYSA-N
Isomeric SMILESNCC(O)C1=CC(O)=C(O)C=C1
Average Molecular Weight169.1778
Monoisotopic Molecular Weight169.073893223
Classification
Description belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 56.80%; H 6.55%; N 8.28%; O 28.37%DFC
Melting PointMp 216.5-218°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-1.24HANSCH,C ET AL. (1995)
Experimental pKapKa3 12 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -37.3DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-7c276dc87ffc587a13a2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-7c276dc87ffc587a13a2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9700000000-f689a79fc40dd7d610c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0089-8079000000-9a53f611d3693ebb51c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0900000000-3d6d08077184bc7a41e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-470ddb022c86b9ee2fdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgr-7900000000-c1bd5e2d31685ca3b0c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-9eabcf1f0c800fc62a37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gi9-0900000000-2ff1cb280b5fe5254689View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4900000000-c16efed37585b9aac58aView in MoNA
ChemSpider ID388394
ChEMBL IDCHEMBL1437
KEGG Compound IDC00547
Pubchem Compound ID439260
Pubchem Substance IDNot Available
ChEBI ID18357
Phenol-Explorer IDNot Available
DrugBank IDDB00368
HMDB IDHMDB00216
CRC / DFC (Dictionary of Food Compounds) IDBLS56-O:BLS57-P
EAFUS IDNot Available
Dr. Duke IDNORADRENALIN|L-NORADRENALINE|NOREPINEPHRINE
BIGG ID35313
KNApSAcK IDC00001424
HET IDLNR
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNorepinephrine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
adrenergic37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
anti shockDUKE
hypertensiveDUKE
inotropicDUKE
neurotransmitter25512 An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.DUKE
sympathomimetic35524 A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.DUKE
vasoconstrictor50514 Drug used to cause constriction of the blood vessels.DUKE
Enzymes
NameGene NameUniProt ID
Alpha-2A adrenergic receptorADRA2AP08913
Alpha-2B adrenergic receptorADRA2BP18089
Phenylalanine-4-hydroxylasePAHP00439
Glycerol kinaseGKP32189
Beta-1 adrenergic receptorADRB1P08588
Beta-2 adrenergic receptorADRB2P07550
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012 map00350
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).