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Chemistry

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Also known as: Noradrenaline, L-noradrenaline, 51-41-2, Arterenol, Levarterenol, (r)-noradrenaline
Molecular Formula
C8H11NO3
Molecular Weight
169.18  g/mol
InChI Key
SFLSHLFXELFNJZ-QMMMGPOBSA-N
FDA UNII
X4W3ENH1CV

Norepinephrine
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 that arises from the LOCUS CERULEUS. It is also found in plants and is used pharmacologically as a sympathomimetic.
Norepinephrine is a Catecholamine.
1 2D Structure

Norepinephrine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
2.1.2 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
2.1.3 InChI Key
SFLSHLFXELFNJZ-QMMMGPOBSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1C(CN)O)O)O
2.1.5 Isomeric SMILES
C1=CC(=C(C=C1[C@H](CN)O)O)O
2.2 Other Identifiers
2.2.1 UNII
X4W3ENH1CV
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Arterenol

2. Levarterenol

3. Levonor

4. Levonorepinephrine

5. Levophed

6. Levophed Bitartrate

7. Noradrnaline Tartrate Renaudin

8. Noradrenaline

9. Noradrenaline Bitartrate

10. Norepinephrin D-tartrate (1:1)

11. Norepinephrine Bitartrate

12. Norepinephrine D-tartrate (1:1)

13. Norepinephrine Hydrochloride

14. Norepinephrine Hydrochloride, (+)-isomer

15. Norepinephrine Hydrochloride, (+,-)-isomer

16. Norepinephrine L-tartrate (1:1)

17. Norepinephrine L-tartrate (1:1), (+,-)-isomer

18. Norepinephrine L-tartrate (1:1), Monohydrate

19. Norepinephrine L-tartrate (1:1), Monohydrate, (+)-isomer

20. Norepinephrine L-tartrate (1:2)

21. Norepinephrine L-tartrate, (+)-isomer

22. Norepinephrine, (+)-isomer

23. Norepinephrine, (+,-)-isomer

2.3.2 Depositor-Supplied Synonyms

1. Noradrenaline

2. L-noradrenaline

3. 51-41-2

4. Arterenol

5. Levarterenol

6. (r)-noradrenaline

7. Levophed

8. (-)-norepinephrine

9. L-norepinephrine

10. (-)-noradrenaline

11. (r)-norepinephrine

12. Levonor

13. L-arterenol

14. 4-[(1r)-2-amino-1-hydroxyethyl]benzene-1,2-diol

15. (-)-arterenol

16. Aktamin

17. Levonoradrenaline

18. Levonorepinephrine

19. Adrenor

20. Sympathin E

21. (r)-(-)-norepinephrine

22. Noradrenalin

23. Norepirenamine

24. Nor-epirenan

25. Norepinephrinum

26. Levoarterenol

27. (r)-4-(2-amino-1-hydroxyethyl)-1,2-benzenediol

28. Norartrinal

29. Nor Adrenalin

30. L-3,4-dihydroxyphenylethanolamine

31. L-1-(3,4-dihydroxyphenyl)-2-aminoethanol

32. L-2-amino-1-(3,4-dihydroxyphenyl)ethanol

33. (-)-(r)-norepinephrine

34. (-)-alpha-(aminomethyl)protocatechuyl Alcohol

35. Nor Adrenalin (tn)

36. L-alpha-(aminomethyl)-3,4-dihydroxybenzyl Alcohol

37. 4-[(1r)-2-amino-1-hydroxyethyl]-1,2-benzenediol

38. 1,2-benzenediol, 4-[(1r)-2-amino-1-hydroxyethyl]-

39. Noradrenalina

40. 1,2-benzenediol, 4-(2-amino-1-hydroxyethyl)-, (r)-

41. Norepinephrine (inn)

42. X4w3enh1cv

43. Nsc-757246

44. Chembl1437

45. 51-41-2 (free Base)

46. Benzyl Alcohol, Alpha-(aminomethyl)-3,4-dihydroxy-, (-)-

47. Noradrenalinum

48. Chebi:18357

49. 4-[(1r)-2-amino-1-hydroxy-ethyl]benzene-1,2-diol

50. Levarterenolo

51. Noreinefrina

52. Levarterenolo [dcit]

53. D-(-)-noradrenaline

54. Noradrenalina [italian]

55. Noradrenalin, L-

56. Norepinephrine [inn]

57. 65277-62-5

58. D-arterenol

59. Noreinefrina [inn-spanish]

60. Norepinephrinum [inn-latin]

61. Norepinefrina

62. Ecteinascidins

63. (+)-noradrenaline

64. 1,2-benzenediol, 4-[(1r)-2-amino-1-hydroxyethyl]-, Homopolymer

65. (?)-norepinephrine

66. Noradrenaline (jp15)

67. Einecs 200-096-6

68. Unii-x4w3enh1cv

69. (-)-arterenol Free Base

70. Norepinephrine Noradrenalin

71. 1,2-benzenediol, 4-((1r)-2-amino-1-hydroxyethyl)-

72. Brn 4231961

73. Nor-adrenaline

74. R-norepinephrine

75. Dermx

76. Norepinephrine [inn:ban:jan]

77. Hsdb 7772

78. E5e

79. (r)-4-(2-amino-1-hydroxyethyl)benzene-1,2-diol

80. Albb-006229

81. Norepinephirine

82. Spectrum_001009

83. Noradrenaline (jp17)

84. Spectrum2_001064

85. Spectrum3_000520

86. Spectrum4_000078

87. Spectrum5_001068

88. Dsstox_cid_3378

89. Bmse000404

90. 1,2-benzenediol,4-(2-amino-1-hydroxyethyl)-

91. Noradrenaline [jan]

92. Norepinephrine [mi]

93. Schembl2609

94. Dsstox_rid_77004

95. Dsstox_gsid_23378

96. Bspbio_002079

97. Gtpl505

98. Kbiogr_000635

99. Kbioss_001489

100. Norepinephrine [hsdb]

101. 4-(2-amino-1-hydroxyethyl)-1,2-benzenediol

102. Mls006010883

103. Divk1c_000230

104. Noradrenaline [mart.]

105. Norepinephrine [vandf]

106. Spectrum1500436

107. Spbio_001048

108. Levarterenol;levophed;arterenol

109. 1,2-benzenediol, 4-((r)-2-amino-1-hydroxyethyl)-

110. Sgcut00123

111. Norepinephrine [who-dd]

112. Dtxsid5023378

113. Hms500l12

114. Kbio1_000230

115. Kbio2_001489

116. Kbio2_004057

117. Kbio2_006625

118. Kbio3_001579

119. Zinc57624

120. D53d5e3a-2360-4ca9-8031-6c2cd4062fd5

121. Ninds_000230

122. Hms1920b08

123. Hms2089e18

124. Hms2091j08

125. Hms3887i07

126. Pharmakon1600-01500436

127. To_000024

128. Tox21_301944

129. Bdbm50029051

130. Ccg-40104

131. Mfcd00025592

132. Norepinephrine [usp Impurity]

133. Nsc757246

134. Pdsp1_001111

135. Pdsp2_001095

136. S9507

137. Stk503776

138. Akos006345192

139. Akos015854572

140. Db00368

141. Nsc 757246

142. Sdccgsbi-0050082.p004

143. Cas-51-41-2

144. Idi1_000230

145. Ncgc00159406-03

146. Ncgc00159406-04

147. Ncgc00159406-05

148. Ncgc00159406-06

149. Ncgc00159406-07

150. Ncgc00159406-08

151. Ncgc00159406-09

152. Ncgc00159406-10

153. Ncgc00159406-11

154. Ncgc00159406-17

155. Ncgc00255328-01

156. As-56654

157. Hy-13715

158. Smr000058585

159. (-)-norepinephrine, >=98%, Crystalline

160. (r)-4-(2-amino-1-hydroxyethyl)catechol

161. Sbi-0050082.p003

162. Adrenaline Impurity B [ep Impurity]

163. Cs-0007744

164. C00547

165. D00076

166. Ab00052424-06

167. Ab00052424_07

168. Ab00052424_08

169. 025n592

170. Q186242

171. Adrenaline Tartrate Impurity B [ep Impurity]

172. W-105896

173. (1r)-2-amino-1-(3,4-dihydroxyphenyl)ethanol

174. (-)-.alpha.-(aminomethyl)-3,4-dihydroxybenzyl Alcohol

175. 1,2-benzenediol, 4-(2-amino-1-hydroxyethyl)-, (r)-(-)-

176. Benzyl Alcohol, .alpha.-(aminomethyl)-3,4-dihydroxy-, (+)-

177. (-)-noradrenaline/ 1,?2-?benzenediol, 4-?[(1r)?-?2-?amino-?1-?hydroxyethyl]?-

178. 1,2-benzenediol, 4-(2-amino-1-hydroxyethyl)-, (r)-(r-(r*,r*))-2,3-dihydroxybutanedioate

179. 86941-27-7

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 169.18 g/mol
Molecular Formula C8H11NO3
XLogP3-1.2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass169.07389321 g/mol
Monoisotopic Mass169.07389321 g/mol
Topological Polar Surface Area86.7 Ų
Heavy Atom Count12
Formal Charge0
Complexity142
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Norepinephrine is used to produce vasoconstriction and cardiac stimulation as an adjunct to correct hemodynamic imbalances in the treatment of shock that persists after adequate fluid volume replacement. /Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1397


Epinephrine is the drug of choice in the emergency treatment of severe acute anaphylactic reactions, including anaphylactic shock. Once adequate ventilation is assured, maintenance of blood pressure in patients with anaphylactic shock may be achieved with other pressor agents, such as norepinephrine. /Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1397


In hypotension associated with myocardial infarction, cautious administration of norepinephrine may be of value and some clinicians consider it to be the pressor drug of choice. However, this type of shock generally has a poor prognosis even when pressor agents are used, and norepinephrine-induced increases in myocardial oxygen demand and the work of the heart may outweigh the beneficial effects of the drug. In addition, cardiac arrhythmias due to the drug are more likely to occur in patients with myocardial infarction. If severe congestive heart failure is also present, dopamine may be preferable because it increases renal blood flow as well as stroke volume. If peripheral vascular resistance is elevated, isoproterenol may be used in conjunction with norepinephrine, but dosage of both drugs must be carefully adjusted according to the specific hemodynamic imbalances present. /Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1397


Norepinephrine may be used to treat hypotension occurring during spinal anesthesia, but other vasopressors having a longer duration of action and which can be administered IM such as metaraminol, methoxamine, or phenylephrine are more commonly used. Norepinephrine may be used to treat hypotension occurring during general anesthesia; however, the possibility of cardiac arrhythmias should be considered. /Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1398


For more Therapeutic Uses (Complete) data for Norepinephrine (7 total), please visit the HSDB record page.


4.2 Drug Warning

Norepinephrine can cause severe peripheral and visceral vasoconstriction, reduced blood flow to vital organs, decreased renal perfusion and therefore decreased urine output, tissue hypoxia, and metabolic acidosis. These effects are most likely to occur in hypovolemic patients. In addition, prolonged use of norepinephrine may cause plasma volume depletion which may result in perpetuation of the shock state or recurrence of hypotension when the drug is discontinued.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1398


Prolonged administration of norepinephrine has caused edema, hemorrhage, focal myocarditis, subpericardial hemorrhage, necrosis of the intestine, or hepatic and renal necrosis. These effects have generally occurred in patients with severe shock and it is not clear if the drug or the shock state itself was the cause.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1399


Norepinephrine can cause tissue necrosis and sloughing at the site of injection as a result of local vasoconstriction. Impairment of circulation and sloughing of tissue may also occur without obvious extravasation. Gangrene of the extremities has been reported rarely and has occurred in a lower extremity when norepinephrine was injected into an ankle vein.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1398


Norepinephrine increases myocardial oxygen consumption and the work of the heart. Cardiac output may be decreased following prolonged use of the drug or administration of large doses because venous return to the heart may be diminished because of increased peripheral vascular resistance. Decreased cardiac output may be especially harmful to elderly patients or those with initially poor cerebral or coronary circulation. Norepinephrine may cause palpitation and bradycardia as well as potentially fatal cardiac arrhythmias, including ventricular tachycardia, bigeminal rhythm, nodal rhythm, atrioventricular dissociation, and fibrillation. Bradycardia may be treated by administration of atropine. Arrhythmias are especially likely to occur in patients with acute myocardial infarction, hypoxia, or hypercapnia, or those receiving other drugs which may increase cardiac irritability such as cyclopropane or halogenated hydrocarbon general anesthetics.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1398


For more Drug Warnings (Complete) data for Norepinephrine (19 total), please visit the HSDB record page.


4.3 Drug Indication

Mainly used to treat patients in vasodilatory shock states such as septic shock and neurogenic shock and has shown a survival benefit over dopamine. Also used as a vasopressor medication for patients with critical hypotension.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 MeSH Pharmacological Classification

Adrenergic alpha-Agonists

Drugs that selectively bind to and activate alpha adrenergic receptors. (See all compounds classified as Adrenergic alpha-Agonists.)


Sympathomimetics

Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)


Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
NOREPINEPHRINE
5.3.2 FDA UNII
X4W3ENH1CV
5.3.3 Pharmacological Classes
Catecholamines [CS]; Catecholamine [EPC]
5.4 ATC Code

C01CA03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CA - Adrenergic and dopaminergic agents

C01CA03 - Norepinephrine


5.5 Absorption, Distribution and Excretion

Norepinephrine localizes mainly in sympathetic nervous tissue. The drug crosses the placenta but not the blood-brain barrier.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1400


Orally ingested norepinephrine is destroyed in the GI tract, and the drug is poorly absorbed after subcutaneous injection. After IV administration, a pressor response occurs rapidly. The drug has a short duration of action, and the pressor action stops within 1-2 minutes after the infusion is discontinued.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1400


Norepinephrine, like epinephrine, is ineffective when given orally and is absorbed poorly from sites of subcutaneous injection. It is rapidly inactivated in the body by the same enzymes that methylate and oxidatively deaminate epinephrine. Small amounts normally are found in the urine. The excretion rate may be greatly increased in patients with pheochromocytoma.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 248


5.6 Metabolism/Metabolites

The pharmacologic actions of norepinephrine are terminated primarily by uptake and metabolism in sympathetic nerve endings. The drug is metabolized in the liver and other tissues by a combination of reactions involving the enzymes catechol-O-methyltransferase (COMT) and monoamine oxidase (MAO). The major metabolites are normetanephrine and 3-methoxy-4-hydroxy mandelic acid (vanillylmandelic acid, VMA), both of which are inactive. Other inactive metabolites include 3-methoxy-4-hydroxyphenylglycol, 3,4-dihydroxymandelic acid, and 3,4-dihydroxyphenylglycol. Norepinephrine metabolites are excreted in urine primarily as the sulfate conjugates and, to a lesser extent, as the glucuronide conjugates. Only small quantities of norepinephrine are excreted unchanged.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1400


5.7 Mechanism of Action

Norepinephrine functions as a peripheral vasoconstrictor by acting on alpha-adrenergic receptors. It is also an inotropic stimulator of the heart and dilator of coronary arteries as a result of it's activity at the beta-adrenergic receptors.


The pharmacological actions of norepinephrine and epinephrine have been extensively compared in vivo and in vitro. Both drugs are direct agonists on effector cells, and their actions differ mainly in the ratio of their effectiveness in stimulating alpha and beta2-receptors. They are approximately equipotent in stimulating beta1-receptors. Norepinephrine is a potent alpha agonist and has relatively little action on beta-2 receptors; however, it is somewhat less potent than epinephrine on the alpha receptors of most organs.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 248


During cold exposures there is an immediate release of catecholamines (e.g., norepinephrine, dopamine), which activate the sympathetic nervous system to reduce heat loss via peripheral vasoconstriction and shift substrate utilization toward fatty acid metabolism for heat production.

Mahar H; Patty's Toxicology CD-ROM (2005). NY, NY: John Wiley & Sons; Cold Stress and Strain. Online Posting Date: April 16, 2001.


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22-Feb-2021
09-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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(USD/KGS)
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