CAS No 586-06-1 , 5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol

Title: Metaproterenol
CAS Registry Number: 586-06-1
CAS Name: 5-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,3-benzenediol
Synonyms: 3,5-dihydroxy-a-[(isopropylamino)methyl]benzyl alcohol; 1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol; 1-(3,5-dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethane; orciprenaline
Molecular Formula: C11H17NO3
Molecular Weight: 211.26
Percent Composition: C 62.54%, H 8.11%, N 6.63%, O 22.72%
Literature References: Prepn and resolution of d- and l-forms: BE 611502; O. Thoma, K. Zeile, US 3341594 (1961, 1967 both to Boehringer, Ing.). Pharmacology: H. H. Pelz, Am. J. Med. Sci. 253, 321 (1967). Metabolism: K. Tatsumi et al., Yakugaku Zasshi 90, 639 (1970); ibid. 91, 680 (1971). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Review of clinical toxicology: J. D. Truwit, Crit. Care Clin. 7, 639-657 (1991).
Properties: Crystals, mp 100°.
Melting point: mp 100°
 
Derivative Type: Sulfate
CAS Registry Number: 5874-97-5
Manufacturers' Codes: TH-152
Trademarks: Alotec (Boehringer, Ing.); Alupent (Boehringer, Ing.); Metaprel (Dorsey); Novasmasol (Zambeletti)
Molecular Formula: (C11H17NO3)2.H2SO4
Molecular Weight: 520.59
Percent Composition: C 50.76%, H 6.97%, N 5.38%, O 30.73%, S 6.16%
Properties: Crystals from 90% ethanol, mp 202-203°. LD50 in rats (mg/kg): 42 orally (Goldenthal).
Melting point: mp 202-203°
Toxicity data: LD50 in rats (mg/kg): 42 orally (Goldenthal)
 
Derivative Type: d-Form hydrochloride
Properties: Crystals, mp 212-213°. [a]D +45.2° (c = 5 in methanol).
Melting point: mp 212-213°
Optical Rotation: [a]D +45.2° (c = 5 in methanol)
 
Derivative Type: l-Form hydrochloride
Properties: Crystals, mp 212°. [a]D -45°.
Melting point: mp 212°
Optical Rotation: [a]D -45°
 
Therap-Cat: Bronchodilator.
Keywords: ?Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives.