5931. Metaproterenol

Nomenclature

CAS number: 586-06-1
5-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,3-benzenediol; 3,5-dihydroxy-α-[(isopropylamino)methyl]benzyl alcohol; 1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol; 1-(3,5-dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethane; orciprenaline.
C11H17NO3; mol wt 211.26.
C 62.54%, H 8.11%, N 6.63%, O 22.72%.

Description and 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).

Chemical structure

Properties

Crystals, mp 100°.

Derivative

Sulfate.

Nomenclature

CAS number: 5874-97-5
TH-152; Alotec (Boehringer, Ing.); Alupent (Boehringer, Ing.); Metaprel (Dorsey); Novasmasol (Zambeletti).
(C11H17NO3)2.H2SO4; mol wt 520.59.
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).

Derivative

d-Form hydrochloride.

Properties

Crystals, mp 212-213°. [α]D +45.2° (c = 5 in methanol).

Derivative

l-Form hydrochloride.

Properties

Crystals, mp 212°. [α]D 45°.

Therapeutic Category

Bronchodilator.

Keywords

β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives