5217. Isoproterenol

Nomenclature

CAS number: 7683-59-2
4-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,2-benzenediol; 3,4-dihydroxy-α-[(isopropylamino)methyl]benzyl alcohol; α-(isopropylaminomethyl)protocatechuyl alcohol; isoprenaline; isopropylarterenol; 1-(3,4-dihydroxyphenyl)-2-isopropylaminoethanol; isopropylaminomethyl-(3,4-dihydroxyphenyl)carbinol; N-isopropyl-β-dihydroxyphenyl-β-hydroxyethylamine; dihydroxyphenylethanolisopropylamine; N-isopropylnoradrenaline; epinephrine isopropyl homolog; A-21; Aludrine; Aleudrin (Lewis); Isuprel (Winthrop); Norisodrine (Abbott); Asiprenol; Asmalar; Neo-Epinine (Burroughs Wellcome); Novodrin; Isupren; Neodrenal; Isopropydrin; Assiprenol; Respifral; Bellasthman; Saventrine (Pharmax); Proternol; Isorenin; Vapo-N-Iso (USV); Isonorin (SM & P).
C11H17NO3; mol wt 211.26.
C 62.54%, H 8.11%, N 6.63%, O 22.72%.

Description and references

β-Adrenergic agonist. Catecholamine derivative prepd by the reaction of 3,4-dihydroxy-α-haloacetophenone with an excess of isopropylamine: Scheuing, Thom, DE 723278 (1942 to Boehringer, Ing.); US 2308232 (1943); from guaiacol and chloral hydrate: Beke et al., Pharm. Zentralhalle 92, 237 (1953). Resolution: Kerschbaum, Benedikt, Monatsh. Chem. 83, 1090 (1952); Beccari et al., Science 118, 249 (1953); Delmar et al., US 2715141 (1955 to Delmar Chem.). Configuration: Pratesi et al., Farmaco Ed. Sci. 15, 3 (1960). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Effect on gastric acid secretion: M. J. Daly, Scand. J. Gastroenterol. 89, 3 (1984). Use in treatment of primary pulmonary hypertension: D. A. Pietro et al., N. Engl. J. Med. 310, 1032 (1984). Review of pharmacology and comparison with other β-adrenoceptor agonists: V. T. Popa, J. Asthma 21, 183-207 (1984). Comprehensive description: M. Tariq, A. A. Al-Badr, Anal. Profiles Drug Subs. 14, 391-422 (1985).

Chemical structure

Derivative

dl-Form.

Properties

Crystals from alc, mp 155.5°. pKa 8.64. LD50 in male, female rats (mg/kg): 3675, 4282 orally (Goldenthal).

Derivative

dl-Form hydrochloride.

Nomenclature

Aerolone (Lilly); Aerotrol (Abbott); Euspiran; Isomenyl (Kaken); Isovon; Mistarel; Suscardia (Pharmax).
C11H17NO3.HCl; mol wt 247.72.
C 53.33%, H 7.32%, N 5.65%, O 19.38%, Cl 14.31%.

Properties

Crystals from alc, mp 170-171°. Soly: one gram dissolves in 3 ml water, in 50 ml ethanol (95%). Less sol in abs ethanol. Practically insol in chloroform, ether, benzene. pH of 1% aq soln about 5. Aq solns turn brownish-pink upon prolonged exposure to air or upon addition of alkali. LD50 orally in rats: 2221 ±93 mg/kg (Goldenthal).

Derivative

dl-Form sulfate dihydrate.

Nomenclature

CAS number: 6700-39-6
Aludrin (Boehringer, Ing.); Isomist; Propal.
(C11H17NO3)2.H2SO4.2H2O; mol wt 556.62.
C 47.47%, H 7.24%, N 5.03%, O 34.49%, S 5.76%.

Properties

Crystals from acetone + methanol, mp 128° (some decomp). One gram dissolves in about 4 ml water. Slightly sol in alc. Practically insol in chloroform, ether, benzene. pH of a 1% aq soln about 5.

Derivative

l-Form.

Properties

Crystals, mp 164-165°. [α]D19 45.0° (c = 2 in 2N HCl).

Derivative

l-Form hydrochloride.

Properties

Crystals, dec 162-164°. [α]D20 50°.

Derivative

l-Form d-bitartrate dihydrate.

Nomenclature

Isolevin.

Properties

Crystals, mp 80-83° (sinters at 78°). [α]D19 14.9° (c = 2.31).

Therapeutic Category

Bronchodilator.

Therapeutic Category (Veterinary)

Sympathomimetic. Chiefly as bronchodilator.

Keywords

β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives