Nepinalone

Nepinalone is a cough suppressant. Its brand names include Placatus, Tussolvina, and Nepitus.

Nepinalone
Clinical data
ATC code
Identifiers
IUPAC name
  • 1-methyl-1-(2-piperidin-1-ylethyl)-3,4-dihydronaphthalen-2(1H)-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
SMILES
  • O=C2C(c1ccccc1CC2)(CCN3CCCCC3)C
InChI
  • InChI=1S/C18H25NO/c1-18(11-14-19-12-5-2-6-13-19)16-8-4-3-7-15(16)9-10-17(18)20/h3-4,7-8H,2,5-6,9-14H2,1H3 Y
  • Key:RVXGRCNWGOHSDE-UHFFFAOYSA-N Y
  (verify)

The effect is evident after 20–30 minutes after administration and persists for at least 4 hours. It acts primarily at the level of the CNS, but also shows a slight activity in inhibiting the bronchospasm. In such use, it is less effective than codeine and more effective than dextromethorphan in inhibiting the tussive stimulus.

Synthesis
Orig patent:[1] Newer Patent:[2]

The starting material is called 2-Phenylpropanoyl Chloride [22414-26-2]. This is reacted with ethylene in the presence of aluminum trichloride catalyst to give 1-methyl-2-tetralone [66405-14-9] (1). Base catalyzed alkylation of this with 1-(2-chloroethyl)piperidine [1932-03-2] (2) gives Nepinalone (3).

References
  1. GB1140990 idem Raffaello Fusco & Franco Tenconi, U.S. Patent 3,576,811 (1971 to Warner Lambert Co LLC).
  2. Franco Tenconi, Silvana Furfaro, EP 0507001 (1992 to BIOINDUSTRIA FARMACEUTICI S.p.A.).


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