Isoproterenol
Title: Isoproterenol
CAS Registry Number: 7683-59-2
CAS Name: 4-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,2-benzenediol
Additional Names: 3,4-dihydroxy-a-[(isopropylamino)methyl]benzyl alcohol; a-(isopropylaminomethyl)protocatechuyl alcohol; isoprenaline; isopropylarterenol; 1-(3,4-dihydroxyphenyl)-2-isopropylaminoethanol; isopropylaminomethyl-(3,4-dihydroxyphenyl)carbinol; N-isopropyl-b-dihydroxyphenyl-b-hydroxyethylamine; dihydroxyphenylethanolisopropylamine; N-isopropylnoradrenaline; epinephrine isopropyl homolog
Manufacturers' Codes: A-21
Trademarks: 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)
Molecular Formula: C11H17NO3
Molecular Weight: 211.26
Percent Composition: C 62.54%, H 8.11%, N 6.63%, O 22.72%
Literature References: b-Adrenergic agonist. Catecholamine derivative prepd by the reaction of 3,4-dihydroxy-a-haloacetophenone with an excess of isopropylamine: Scheuing, Thomä, 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 b-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).
 
Derivative Type: dl-Form
Properties: Crystals from alc, mp 155.5°. pKa 8.64. LD50 in male, female rats (mg/kg): 3675, 4282 orally (Goldenthal).
Melting point: mp 155.5°
pKa: pKa 8.64
Toxicity data: LD50 in male, female rats (mg/kg): 3675, 4282 orally (Goldenthal)
 
Derivative Type: dl-Form hydrochloride
Trademarks: Aerolone (Lilly); Aerotrol (Abbott); Euspiran; Isomenyl (Kaken); Isovon; Mistarel; Suscardia (Pharmax)
Molecular Formula: C11H17NO3.HCl
Molecular Weight: 247.72
Percent Composition: 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).
Melting point: mp 170-171°
Toxicity data: LD50 orally in rats: 2221 ±93 mg/kg (Goldenthal)
 
Derivative Type: dl-Form sulfate dihydrate
CAS Registry Number: 6700-39-6
Trademarks: Aludrin (Boehringer, Ing.); Isomist; Propal
Molecular Formula: (C11H17NO3)2.H2SO4.2H2O
Molecular Weight: 556.62
Percent Composition: 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.
Melting point: mp 128° (some decomp)
 
Derivative Type: l-Form
Properties: Crystals, mp 164-165°. [a]D19 -45.0° (c = 2 in 2N HCl).
Melting point: mp 164-165°
Optical Rotation: [a]D19 -45.0° (c = 2 in 2N HCl)
 
Derivative Type: l-Form hydrochloride
Properties: Crystals, dec 162-164°. [a]D20 -50°.
Optical Rotation: [a]D20 -50°
 
Derivative Type: l-Form d-bitartrate dihydrate
Trademarks: Isolevin
Properties: Crystals, mp 80-83° (sinters at 78°). [a]D19 -14.9° (c = 2.31).
Melting point: mp 80-83° (sinters at 78°)
Optical Rotation: [a]D19 -14.9° (c = 2.31)
 
Therap-Cat: Bronchodilator.
Therap-Cat-Vet: Sympathomimetic. Chiefly as bronchodilator.
Keywords: ?Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives.

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