Hydroxyphenamate

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]

Hydroxyphenamate

Clinical data
Trade names	Listica
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1]
Identifiers
IUPAC name (2-hydroxy-2-phenylbutyl) carbamate
CAS Number	50-19-1 Y
PubChem CID	5752
ChemSpider	5549
UNII	MD0414799X
KEGG	D04476
ChEBI	CHEBI:134877
ChEMBL	ChEMBL2107215
CompTox Dashboard (EPA)	DTXSID40861571
ECHA InfoCard	100.000.016
Chemical and physical data
Formula	C11H15NO3
Molar mass	209.245 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(COC(=O)N)(C1=CC=CC=C1)O
InChI InChI=1S/C11H15NO3/c1-2-11(14,8-15-10(12)13)9-6-4-3-5-7-9/h3-7,14H,2,8H2,1H3,(H2,12,13) Key:WAFIYOULDIWAKR-UHFFFAOYSA-N

Synthesis

The reaction of propiophenone (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 with ethyl chloroformate followed by addition of aqueous ammonia gave the carbamate, and hence hydroxyphenamate (5).

Synthesis of hydroxyphenamate