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Benproperine

Summary

Benproperine (INN) is a cough suppressant.[1] It has been marketed in multiple countries in Central America and Europe, as the phosphate or pamoate salts in either tablet, dragée, or syrup form. Trade names include Blascorid in Italy and Sweden, Pectipront and Tussafug in Germany, and Pirexyl in Scandinavia. The recommended dosage for adults is 25 to 50 mg two to four times daily, and for children 25 mg once or twice daily. Adverse effects include dry mouth, dizziness, fatigue, and heartburn.[2]

Benproperine
Clinical data
Trade namesBlascorid, Pectipront, Pirexyl, Tussafug
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (RS)-1-[2-(2-benzylphenoxy)-1-methylethyl]piperidine
CAS Number
PubChem CID
  • 2326
ChemSpider
  • 2236 checkY
UNII
  • 3AA6IZ48YK
KEGG
  • D07512 checkY
ChEMBL
  • ChEMBL2105910
CompTox Dashboard (EPA)
  • DTXSID10862853 Edit this at Wikidata
Chemical and physical data
FormulaC21H27NO
Molar mass309.453 g·mol−1
3D model (JSmol)
  • Interactive image
  • O(c1ccccc1Cc2ccccc2)CC(N3CCCCC3)C
  • InChI=1S/C21H27NO/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3 checkY
  • Key:JTUQXGZRVLWBCR-UHFFFAOYSA-N checkY
  (verify)

Synthesis edit

 
Thieme Patents:[3][4] Revised:[5] China:[6]

The base catalyzed ether formation between 2-Benzylphenol [28994-41-4] (1) and 1,2-dichloropropane (2) gives 1-benzyl-2-(2-chloropropoxy)benzene [85909-36-0] (3). Displacement of the remaining halogen with piperidine completes the synthesis of benproperine (4).

References edit

  1. ^ Li Y, Zhong DF, Chen SW, Maeba I (December 2005). "Identification of some benproperine metabolites in humans and investigation of their antitussive effect". Acta Pharmacologica Sinica. 26 (12): 1519–26. doi:10.1111/j.1745-7254.2005.00212.x. PMID 16297353.
  2. ^ Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 6. ISBN 0-8103-7177-4.
  3. ^ DK96113 idem Rubenstein K, GB 914008  (1962 to Pharmacia AS).
  4. ^ Kurt Rubinstein, U.S. patent 3,117,059 (1964 to Aktieselskabet Pharmacia).
  5. ^ Byoung Mog Kwon, et al. WO 2012064150  (to Korea Research Institute of Bioscience and Biotechnology KRIBB).
  6. ^ Chin. J. Org. Chem. 2011, Vol. 31, Issue (02): 212-215.