Hydroxyphenamate

Hydroxyphenamate
Clinical data
Trade names	Listica
Legal status
Legal status	BR: Class C1 (Other controlled substances);
Identifiers
	IUPAC name (2-hydroxy-2-phenylbutyl) carbamate;
CAS Number	50-19-1 ;
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;

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 (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

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ American Medical Association Dept of Drugs (1977). AMA Drug Evaluations (3rd ed.). Littleton, Mass.: Pub. Sciences Group. p. N-61. ISBN 978-0-88416-175-2. OCLC 1024170745.
^ Lednicer & Mitscher, book 1, page 220.
^ Robert H Sifferd & Leo D Braitberg, U.S. patent 3,066,164 (1962 to Armour Pharmaceutical Co)

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] American Medical Association Dept of Drugs (1977). AMA Drug Evaluations (3rd ed.). Littleton, Mass.: Pub. Sciences Group. p. N-61. ISBN 978-0-88416-175-2. OCLC 1024170745.

[3] Lednicer & Mitscher, book 1, page 220.

[4] Robert H Sifferd & Leo D Braitberg, U.S. patent 3,066,164 (1962 to Armour Pharmaceutical Co)

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