Metaraminol
Title: Metaraminol
CAS Registry Number: 54-49-9
CAS Name: (aR)-a-[(1S)-1-Aminoethyl]-3-hydroxybenzenemethanol
Additional Names: (-)-a-(1-aminoethyl)-m-hydroxybenzyl alcohol; m-hydroxynorephedrine; m-hydroxypropadrine; m-hydroxyphenylpropanolamine; m-hydroxy-a-(1-aminoethyl)benzyl alcohol; 2-amino-1-(m-hydroxyphenyl)-1-propanol; 1-(m-hydroxyphenyl)-2-amino-1-propanol; a-(m-hydroxyphenyl)-b-aminopropanol; metaradrine
Molecular Formula: C9H13NO2
Molecular Weight: 167.21
Percent Composition: C 64.65%, H 7.84%, N 8.38%, O 19.14%
Literature References: Prepn from m-hydroxyisonitrosopropiophenone: GB 353361 (1930 to I. G. Farben); l-form: GB 396951 (1932 to I. G. Farben); from l-m-hydroxyphenylacetylcarbinol: CH 162367 (1931 to I. G. Farben); see also US 1948162 and US 1951302; Hartung, US 1995709 (1935 to Sharp & Dohme). Pharmacology: A. Cession-Fossion, Arch. Int. Pharmacodyn. Ther. 172, 421 (1968). Toxicity data: O. H. Siegmund et al., J. Pharmacol. Exp. Ther. 92, 207 (1948).
 
Derivative Type: Bitartrate
CAS Registry Number: 33402-03-8
Trademarks: Aramine (Merck & Co.); Araminon (Banyu)
Molecular Formula: C13H19NO8
Molecular Weight: 317.29
Percent Composition: C 49.21%, H 6.04%, N 4.41%, O 40.34%
Properties: Crystals, mp 176-177°. Freely sol in water. pH of 1% aq soln about 3.5.
Melting point: mp 176-177°
 
Derivative Type: Hydrochloride
CAS Registry Number: 5967-52-2
Molecular Formula: C9H13NO2.HCl
Molecular Weight: 203.67
Percent Composition: C 53.07%, H 6.93%, N 6.88%, O 15.71%, Cl 17.41%
Properties: Hygroscopic crystals, [a]D20 -19.75°. Freely sol in water. LD50 i.p. in mice: 440 mg/kg (Siegmund).
Optical Rotation: [a]D20 -19.75°
Toxicity data: LD50 i.p. in mice: 440 mg/kg (Siegmund)
 
Derivative Type: Oxalate dihydrate
CAS Registry Number: 5967-53-3
Molecular Formula: C9H13NO2.C2H2O4.2H2O
Molecular Weight: 293.27
Percent Composition: C 45.05%, H 6.53%, N 4.78%, O 43.64%
Properties: Crystals, mp 190°. [a]D20 -21.66°. Sol in water.
Melting point: mp 190°
Optical Rotation: [a]D20 -21.66°
 
Therap-Cat: Adrenergic.
Keywords: a-Adrenergic Agonist; Antihypotensive.

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