Benproperine
Chemical compound
- R05DB02 (WHO)
- (RS)-1-[2-(2-benzylphenoxy)-1-methylethyl]piperidine
- 2156-27-6
Y 19428-14-9 (phosphate salt)
- 2326
- 2236 Y
- 3AA6IZ48YK
- D07512 Y
- ChEMBL2105910
- DTXSID10862853
- Interactive image
- O(c1ccccc1Cc2ccccc2)CC(N3CCCCC3)C
InChI
- 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,3,8-9,14-17H2,1H3Y
- Key:JTUQXGZRVLWBCR-UHFFFAOYSA-NY
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]
Synthesis
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
- ^ 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.
- ^ Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 6. ISBN 0-8103-7177-4.
- ^ DK96113 idem Rubenstein K, GB 914008 (1962 to Pharmacia AS).
- ^ Kurt Rubinstein, U.S. patent 3,117,059 (1964 to Aktieselskabet Pharmacia).
- ^ Byoung Mog Kwon, et al. WO 2012064150 (to Korea Research Institute of Bioscience and Biotechnology KRIBB).
- ^ Chin. J. Org. Chem. 2011, Vol. 31, Issue (02): 212-215.
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- ‡Withdrawn from market
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