Back to Compounds

(R)-Norepinephrine (PC000339)

Record Information
Version1.0
Creation date2015-10-09 22:30:01 UTC
Update date2017-01-19 02:36:20 UTC
FoodComEx IDPC000339
FoodDB RecordNot Available
Chemical Information
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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-(r)-norepinephrinebiospider
(-)-alpha-(aminomethyl)protocatechuyl alcoholbiospider
(-)-arterenolbiospider
(-)-noradrenalinebiospider
(-)-norepinephrinebiospider
(CF2Cl)2biospider
(r)-(-)-norepinephrinebiospider
(R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediolbiospider
(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]-1,2-benzenediolbiospider
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diolbiospider
51-40-1 (l-tartrate (1:1))biospider
Adrenordb_source
Aktaminbiospider
Arcton 114biospider
Arcton 33biospider
Arterenolbiospider
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
Levarterenoldb_source
Levarterenolobiospider
Levarterenolo [dcit]biospider
Levoarterenolbiospider
Levonorbiospider
Levonoradrenalinebiospider
Levonorepinephrinebiospider
Levopheddb_source
Levophed bitartratebiospider
Nor adrenalinbiospider
Nor adrenalin (TN)biospider
Nor-epirenanbiospider
Noradrenalinbiospider
Noradrenalin, l-biospider
Noradrenalinabiospider
Noradrenalinebiospider
Noradrenaline (JP15)biospider
Noradrenaline bitartratebiospider
Noradrenalinumbiospider
Norartrinalbiospider
Noreinefrinabiospider
Norepinefrinabiospider
Norepinephrinebiospider
Norepinephrine (inn)biospider
Norepinephrine [inn:jan]biospider
Norepinephrine l-Tartrate (1:1)biospider
Norepinephrine noradrenalinbiospider
Norepinephrinumbiospider
Norepirenaminebiospider
Propellant 114biospider
Refrigerant 114biospider
Refrigerant R114biospider
S-dichlorotetrafluoroethanebiospider
SYM-dichlorotetrafluoroethanebiospider
Sympathin ebiospider
Chemical FormulaNot Available
IUPAC nameNot Available
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-1.24HANSCH,C ET AL. (1995)
Experimental Water SolubilityNot Available
Melting PointMp 216.5-218°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 500 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available