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Substance Name: Norepinephrine [INN:BAN:JAN]
RN: 51-41-2
UNII: X4W3ENH1CV
InChIKey: SFLSHLFXELFNJZ-QMMMGPOBSA-N

Note

  • 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.

Molecular Formula

  • C8-H11-N-O3

Molecular Weight

  • 169.1789
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Agonists
  • Adrenergic alpha-Agonists
  • Autonomic Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Mutation Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sympathomimetics
  • Vasoconstrictor Agents

Names and Synonyms

Name of Substance

  • Norepinephrine
  • Norepinephrine [INN:BAN:JAN]

MeSH Heading

  • Norepinephrine

Synonyms

  • (-)-alpha-(Aminomethyl)protocatechuyl alcohol
  • (-)-Arterenol
  • (-)-Noradrenaline
  • (-)-Norepinephrine
  • (R)-(-)-Norepinephrine
  • (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol
  • (R)-Noradrenaline
  • (R)-Norepinephrine
  • Adrenor
  • Aktamin
  • Arterenol
  • BRN 4231961
  • D-(-)-Noradrenaline
  • EINECS 200-096-6
  • HSDB 7772
  • l-1-(3,4-Dihydroxyphenyl)-2-aminoethanol
  • 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
  • Levarterenolo
  • Levarterenolo [DCIT]
  • Levonor
  • Levonoradrenaline
  • Levonorepinephrine
  • Levophed
  • Nor-Epirenan
  • Noradrenalin
  • Noradrenalin, l-
  • Noradrenalina
  • Noradrenalina [Italian]
  • Noradrenaline
  • Noradrenalinum
  • Norartrinal
  • Noreinefrina
  • Noreinefrina [INN-Spanish]
  • Norepinephrine
  • Norepinephrinum
  • Norepinephrinum [INN-Latin]
  • Norepirenamine
  • Sympathin E
  • UNII-X4W3ENH1CV

Systematic Names

  • 1,2-Benzenediol, 4-((1R)-2-amino-1-hydroxyethyl)-
  • 1,2-Benzenediol, 4-((R)-2-amino-1-hydroxyethyl)-
  • 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)- (9CI)
  • Benzyl alcohol, alpha-(aminomethyl)-3,4-dihydroxy-, (-)-
  • Norepinephrine

Registry Numbers

CAS Registry Number

  • 51-41-2

FDA UNII

  • X4W3ENH1CV

Other Registry Numbers

  • 4899-05-2
  • 66197-73-7

Related Registry Number

  • 51-40-1 (l-tartrate (1:1))

System Generated Number

  • 0000051412

Structure Descriptors

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

InChIKey

SFLSHLFXELFNJZ-QMMMGPOBSA-N

Smiles

c1cc(c(cc1[C@H](CN)O)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 6mg/kg (6mg/kg)   Drugs in Japan Vol. 6, Pg. 567, 1982.
mouse LD50 intravenous 550ug/kg (0.55mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 226, Pg. 493, 1955.
mouse LD50 oral 20mg/kg (20mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 49, 1972.
mouse LD50 subcutaneous 5mg/kg (5mg/kg)   Naturwissenschaften. Vol. 56, Pg. 615, 1969.
rabbit LDLo intravenous 250ug/kg (0.25mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 41, Pg. 365, 1931.
rat LD50 intravenous 100ug/kg (0.1mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 502, 1949.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 217 dec deg C   EXP
pKa Dissociation Constant 8.58 (none)   EXP
log P (octanol-water) -1.24E+00 (none)   EXP
Water Solubility 1.00E+06 mg/L 25 EST
Vapor Pressure 8.19E-07 mm Hg 25 EST
Henry's Law Constant 3.21E-19 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.49E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.