Benproperine

Benproperine
Clinical data
Trade names	Blascorid, Pectipront, Pirexyl, Tussafug
AHFS/Drugs.com	International Drug Names
ATC code	R05DB02 (WHO) ;
Identifiers
	IUPAC name (RS)-1-[2-(2-benzylphenoxy)-1-methylethyl]piperidine;
CAS Number	2156-27-6 19428-14-9 (phosphate salt);
PubChem CID	2326;
ChemSpider	2236 ;
UNII	3AA6IZ48YK;
KEGG	D07512 ;
ChEMBL	ChEMBL2105910;
CompTox Dashboard (EPA)	DTXSID10862853 ;
Chemical and physical data
Formula	C21H27NO
Molar mass	309.453 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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,3,8-9,14-17H2,1H3 ; Key:JTUQXGZRVLWBCR-UHFFFAOYSA-N ;
	(verify)

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

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

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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[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.