Norepinephrine (medication)

Norepinephrine
	Skeletal formula of noradrenaline
	Ball-and-stick model of the zwitterionic form of noradrenaline found in the crystal structure
Clinical data
Trade names	Levarterenol, Levophed, Norepin, other
Other names	Noradrenaline; (R)-(–)-Norepinephrine; l-1-(3,4-Dihydroxyphenyl)-2-aminoethanol; 3,4,β-Trihydroxyphenethylamine
AHFS/Drugs.com	Monograph
License data	US DailyMed: Norepinephrine; US FDA: Norepinephrine;
Pregnancy; category	AU: B3;
Routes of; administration	Intravenous
Drug class	Adrenergic receptor agonist; Sympathomimetic
ATC code	C01CA03 (WHO) ;
Physiological data
Source tissues	Locus coeruleus; sympathetic nervous system; adrenal medulla
Target tissues	System-wide
Receptors	α1, α2, β1, β3
Agonists	Sympathomimetic drugs, clonidine, isoprenaline
Antagonists	Tricyclic antidepressants, Beta blockers, antipsychotics
Metabolism	MAO-A; COMT
Legal status
Legal status	AU: S4 (Prescription only); CA: OTC; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Metabolism	MAO-A; COMT
Excretion	Urine (84–96%)
Identifiers
	IUPAC name 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol;
CAS Number	51-41-2 ;
PubChem CID	439260;
IUPHAR/BPS	505;
DrugBank	DB00368 ;
ChemSpider	388394 ;
UNII	X4W3ENH1CV;
KEGG	D00076 ; as salt: D05206 ;
ChEBI	CHEBI:18357 ;
ChEMBL	ChEMBL1437 ;
Chemical and physical data
Formula	C8H11NO3
Molar mass	169.180 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.397±0.06 g/cm3
Melting point	217 °C (423 °F) (decomposes)
Boiling point	442.6 °C (828.7 °F) ±40.0°C
	SMILES Oc1ccc(cc1O)[C@@H](O)CN;
	InChI 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 ; Key:SFLSHLFXELFNJZ-QMMMGPOBSA-N ;
	(verify)

Norepinephrine, also known as noradrenaline and sold under the brand name Levophed among others, is a medication used to treat people with very low blood pressure.^[2] It is the typical medication used in sepsis if low blood pressure does not improve following intravenous fluids.^[3] It is the same molecule as the hormone and neurotransmitter norepinephrine.^[2] It is given by slow injection into a vein.^[2]

Common side effects include headache, slow heart rate, and anxiety.^[2] Other side effects include an irregular heartbeat.^[2] If it leaks out of the vein at the site it is being given, norepinephrine can result in limb ischemia.^[2] If leakage occurs the use of phentolamine in the area affected may improve outcomes.^[2] Norepinephrine works by binding and activating alpha adrenergic receptors.^[2]

Norepinephrine was discovered in 1946 and was approved for medical use in the United States in 1950.^[2]^[4] It is available as a generic medication.^[2]

^ Andersen AM (1975). "Structural studies of metabolic products of dopamine. IV. Crystal and molecular structure of (-)-noradrenaline". Acta Chemica Scandinavica B. 29 (8): 871–876. doi:10.3891/acta.chem.scand.29b-0871. PMID 1202890.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Norepinephrine Bitartrate". The American Society of Health-System Pharmacists. Archived from the original on 26 March 2017. Retrieved 26 March 2017.
^ Latifi R (2016). Surgical Decision Making: Beyond the Evidence Based Surgery. Springer. p. 67. ISBN 9783319298245. Archived from the original on 2017-03-27.
^ Encyclopedia of the Neurological Sciences. Academic Press. 2014. p. 224. ISBN 9780123851581. Archived from the original on 2017-03-27.

[1] Andersen AM (1975). "Structural studies of metabolic products of dopamine. IV. Crystal and molecular structure of (-)-noradrenaline". Acta Chemica Scandinavica B. 29 (8): 871–876. doi:10.3891/acta.chem.scand.29b-0871. PMID 1202890.

[AHFS2017-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Norepinephrine Bitartrate". The American Society of Health-System Pharmacists. Archived from the original on 26 March 2017. Retrieved 26 March 2017.

[3] Latifi R (2016). Surgical Decision Making: Beyond the Evidence Based Surgery. Springer. p. 67. ISBN 9783319298245. Archived from the original on 2017-03-27.

[4] Encyclopedia of the Neurological Sciences. Academic Press. 2014. p. 224. ISBN 9780123851581. Archived from the original on 2017-03-27.

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