vadocaine
vadocaine Basic information
- Product Name:
- vadocaine
- Synonyms:
-
- vadocaine
- N-(2-Methoxy-4,6-dimethylphenyl)-2-methyl-1-piperidinepropanamide
- OR-K-242
- Vadocaina
- Vadocainum
- CAS:
- 72005-58-4
- MF:
- C18H28N2O2
- MW:
- 304.431
- Mol File:
- 72005-58-4.mol
vadocaine Usage And Synthesis
Originator
Vadocaine hydrochloride ,ZYF Pharm Chemical
Uses
Vadocaine (OR K-242), an orally active antitussive compound, is a local agent that can suppress or relieve pain[1].
Manufacturing Process
3-Chloro-4',6'-dimethyl-o-propananisidide was prepared by using 92.8 g (0.615 mol) 4,6-dimethyl-o-anisidine and 86 g (0.68 mol) of 3-chloropropionyl chloride, melting point 123-125°C. A mixture containing 40 g (0.165 mol) of 3-chloro-4',6'-dimethyl-o-propananisidide, 54.3 g of 3-methyl piperidine, and 330 ml of anhydrous benzene was heated for 72 hours at 65°C. 47.7 g (84.5%) of N-(2-methoxy-4,6-dimethylphenyl)-2-methyl-1- piperidinepropanamide hydrochloride was obtained by deposition of product in anhydrous acetone saturated with hydrogen chloride; melting point 192-193°C (crystallization from a mixture isopropanol-acetone).
Therapeutic Function
Antitussive, Local anesthetic
in vivo
In guinea-pigs, Vadocaine (2.5 mg/kg; p.o.) reduces by about 70% the cough episodes induced by sulphur dioxide or ammonia[1].
In cats, Vadocaine (3 mg/kg; i.v.) inhibits by about 80% for 10 min the cough reflex initiated by mechanical irritation of the trachea[1].
Vadocaine causes local anaesthesia in the guinea-pig wheal preparation at concentrations of 0.25% and 0.5%, and on the guinea-pig cornea at 0.5%[1].
References
[1] P T M?nnist?, et al. Antitussive action of the new anilide derivative vadocaine hydrochloride compared with codeine phosphate in four animal models. Arzneimittelforschung. 1988 Apr;38(4A):598-604. PMID:3395394
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