Norepinephrine
Title: Norepinephrine
CAS Registry Number: 51-41-2
CAS Name: 4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol
Additional Names: (-)-a-(aminomethyl)-3,4-dihydroxybenzyl alcohol; l-3,4-dihydroxyphenylethanolamine; noradrenaline; levarterenol
Trademarks: Adrenor; Levophed (Winthrop)
Molecular Formula: C8H11NO3
Molecular Weight: 169.18
Percent Composition: C 56.79%, H 6.55%, N 8.28%, O 28.37%
Literature References: Demethylated precursor of epinephrine, q.v. Occurs in animals and man, and is a sympathomimetic hormone of both adrenal origin and adrenergic orthosympathetic postganglionic origin in man. Physiologic review: Malmejac, Physiol. Rev. 44, 186 (1964). It has also been found in plants, e.g., Portulaca olerocea L., Portulacaceae: Fing et al., Nature 191, 1108 (1961). Synthesis of dl-form: Payne, Ind. Chem. 37, 523 (1961). Historic review of synthesis: Loewe, Arzneim.-Forsch. 4, 583 (1954). Resolution of dl-form: Tullar, J. Am. Chem. Soc. 70, 2067 (1948); idem, US 2774789 (1956 to Sterling Drug). Configuration: Pratesi et al., J. Chem. Soc. 1959, 4062. Comprehensive description: C. F. Schwender, Anal. Profiles Drug Subs. 1, 149-173 (1972); T. D. Wilson, ibid. 11, 555-586 (1982).
Properties: Microcrystals, dec 216.5-218°. [a]D25 -37.3° (c = 5 in water with 1 equiv HCl).
Optical Rotation: [a]D25 -37.3° (c = 5 in water with 1 equiv HCl)
 
Derivative Type: Hydrochloride
CAS Registry Number: 329-56-6
Trademarks: Arterenol (HMR)
Molecular Formula: C8H11NO3.HCl
Molecular Weight: 205.64
Percent Composition: C 46.73%, H 5.88%, N 6.81%, O 23.34%, Cl 17.24%
Properties: Crystals, mp 145.2-146.4°. [a]D25 -40° (c = 6). Freely sol in water. Solns slowly oxidize under the influence of light and oxygen in a manner comparable to epinephrine hydrochloride.
Melting point: mp 145.2-146.4°
Optical Rotation: [a]D25 -40° (c = 6)
 
Derivative Type: d-Bitartrate
CAS Registry Number: 69815-49-2
Additional Names: Levarterenol bitartrate
Trademarks: Aktamin; Binodrenal
Molecular Formula: C8H11NO3.C4H6O6
Molecular Weight: 319.26
Percent Composition: C 45.14%, H 5.37%, N 4.39%, O 45.10%
Properties: Obtained as the monohydrate, crystals, mp 102-104°. [a]D25 -10.7° (c = 1.6 in H2O). When anhydr, mp 158-159° (some decompn). Freely sol in water.
Melting point: mp 102-104°; mp 158-159° (some decompn)
Optical Rotation: [a]D25 -10.7° (c = 1.6 in H2O)
 
Derivative Type: dl-Form
Properties: Crystals, dec 191°. Sparingly sol in water; very slightly sol in alc, ether; readily sol in dilute acids, caustic.
 
Therap-Cat: Adrenergic (vasopressor); antihypotensive.
Therap-Cat-Vet: Sympathomimetic; vasopressor in shock.
Keywords: a-Adrenergic Agonist; Antihypotensive.

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