 | |
| Clinical data | |
|---|---|
| Trade names | Listica |
| Legal status | |
| Legal status | |
| Identifiers | |
| |
| CAS Number |
|
| PubChemCID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.000.016 |
| Chemical and physical data | |
| Formula | C11H15NO3 |
| Molar mass | 209.245 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
Hydroxyphenamate oroxyfenamate (trade nameListica) is asedative andanxiolytic drug of thecarbamate class which is no longer marketed in the US. Like other carbamate sedatives, it is chemically related tomeprobamate (Miltown). It was introduced to the US market in 1961. The dosage for adults is 200 mg 3 to 4 times daily.[2]
The reaction ofpropiophenone (1) with cyanide gives 2-hydroxy-2-phenylbutanenitrile (2).[3][4] Acid hydrolysis of the nitrile to a carboxylic acid gives 2-hydroxy-2-phenylbutanoic acid (3). The reduction by hydride of the acid to the alcohol gives 2-phenyl-1,2-butanediol (4). For the final step in the synthesis, treatment withethyl chloroformate followed by addition of aqueousammonia gave the carbamate, and hence hydroxyphenamate (5).
