2347. Clenbuterol

Nomenclature

CAS number: 37148-27-9
4-Amino-3,5-dichloro-α-[[(1,1-dimethylethyl)amino]methyl]benzenemethanol; 4-amino-α-[(tert-butylamino)methyl]-3,5-dichlorobenzyl alcohol; NAB-365; Monores (Valeas).
C12H18Cl2N2O; mol wt 277.19.
C 52.00%, H 6.55%, Cl 25.58%, N 10.11%, O 5.77%.

Description and references

Substituted phenylethanolamine with β2 sympathomimetic activity. Prepn: J. Keck et al., ZA 6705692; eidem, US 3536712 (1968, 1970 both to Thomae); eidem, Arzneim.-Forsch. 22, 861 (1972). Series of articles on pharmacology, reproductive toxicology, pharmacokinetics and metabolism: ibid. 26, 1403-1419, 1427-1460 (1976). Toxicity: M. Ueberberg et al., ibid. 1420. Clinical studies: M. Tschan et al., Eur. J. Clin. Pharmacol. 15, 159 (1979); C. Pasotti et al., Int. J. Clin. Pharmacol. Biopharm. 17, 176 (1979). Effect on weight gain in lambs: M. E. Nichols et al., 1991 Animal Science Research Report (Oklahoma Agric. Exp. Station, Oklahoma State University, 1991) 303.

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 21898-19-1
NAB-365Cl; Spiropent (Thomae; Boehringer, Ing.); Ventipulmin (Boehringer, Ing.).
C12H18Cl2N2O.HCl; mol wt 313.65.
C 45.95%, H 6.11%, Cl 33.91%, N 8.93%, O 5.10%.

Properties

Colorless microcrystalline powder from isopropyl alc, mp 174-175.5°. Very sol in water, methanol, ethanol, slightly sol in chloroform. Insol in benzene. LD50 in mice, rats, guinea pigs (mg/kg): 176, 315, 67.1 orally; 27.6, 35.3, 12.6 i.v. (Ueberberg).

Therapeutic Category

Bronchodilator.

Therapeutic Category (Veterinary)

Bronchodilator; tocolytic.

Keywords

β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives