Hydroxyphenamate or oxyfenamate (trade name Listica) is a
sedative and
anxiolytic drug of the
carbamate class which is no longer marketed in the US. Like other carbamate sedatives, it is chemically related to
meprobamate (Miltown). It was introduced to the US market in 1961. The dosage for adults is 200 mg 3 to 4 times daily.[2]
Synthesis
The reaction of
Propiophenone [93-55-0] (1) with cyanide gives 2-hydroxy-2-phenylbutanenitrile
CID:13089766 (2). Acid hydrolysis of the nitrile to a carboxylic acid gives 2-hydroxy-2-phenylbutanoic acid [35468-69-0] (3). The reduction by hydride of the acid to the alcohol gives 2-phenyl-1,2-butanediol,
CID:13260818 (4).
For the final step in the synthesis, treatment with
Ethyl chloroformate followed by addition of aqueous
ammonia gave the carbamate, and hence hydroxyphenamate (5).
^American Medical Association Dept of Drugs (1977). AMA Drug Evaluations (3rd ed.). Littleton, Mass.: Pub. Sciences Group. p. N-61.
ISBN978-0-88416-175-2.
OCLC1024170745.