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{{short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 413885787 |
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| verifiedrevid = 447813319 |
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| IUPAC_name = 1-piperidine |
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| IUPAC_name = (''RS'')-1-piperidine |
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| image = (RS)-Benproperine Enantiomers Formulae V.1.svg |
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| image = benproperine.png |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Blascorid, Pectipront, Pirexyl, Tussafug |
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| Drugs.com = {{drugs.com|international|benproperine}} |
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| Drugs.com = {{drugs.com|international|benproperine}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 2156-27-6 |
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| CAS_number = 2156-27-6 |
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| CAS_supplemental = 19428-14-9 (] salt) |
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| CAS_supplemental = 19428-14-9 (] salt) |
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| ATC_suffix = DB02 |
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| ATC_suffix = DB02 |
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| PubChem = 2326 |
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| PubChem = 2326 |
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| ChEMBL = 2105910 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07512 |
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| KEGG = D07512 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=21 | H=27 | N=1 | O=1 |
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| C=21 | H=27 |
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| N=1 | O=1 |
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| molecular_weight = 309.445 g/mol |
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| smiles = O(c1ccccc1Cc2ccccc2)CC(N3CCCCC3)C |
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| smiles = O(c1ccccc1Cc2ccccc2)CC(N3CCCCC3)C |
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| InChI = 1/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 |
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| InChIKey = JTUQXGZRVLWBCR-UHFFFAOYAA |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey = JTUQXGZRVLWBCR-UHFFFAOYSA-N |
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| StdInChIKey = JTUQXGZRVLWBCR-UHFFFAOYSA-N |
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}} |
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}} |
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'''Benproperine''' (]) is a ].<ref>{{cite journal | vauthors = Li Y, Zhong DF, Chen SW, Maeba I | title = Identification of some benproperine metabolites in humans and investigation of their antitussive effect | journal = Acta Pharmacologica Sinica | volume = 26 | issue = 12 | pages = 1519–26 | date = December 2005 | pmid = 16297353 | doi = 10.1111/j.1745-7254.2005.00212.x | doi-access = free }}</ref> It has been marketed in multiple countries in Central America and Europe, as the ] or ] salts in either tablet, ], 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.<ref>{{cite book |isbn=0-8103-7177-4 |title=Drugs Available Abroad, 1st Edition |page=6 |date=1991 | vauthors = Schlesser JL |publisher=Derwent Publications Ltd.}}</ref> |
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'''Benproperine''' (]) is a ]. |
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==Synthesis== |
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Patents:<ref>DK96113 idem Rubenstein K, {{Cite patent|GB|914008}} (1962 to Pharmacia AS). </ref><ref>Kurt Rubinstein, {{US patent|3117059}} (1964 to Aktieselskabet Pharmacia).</ref> Revised:<ref>Byoung Mog Kwon, et al. {{Cite patent|WO|2012064150}} (to Korea Research Institute of Bioscience and Biotechnology KRIBB).</ref> China:<ref></ref>]] |
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The base catalyzed ether formation between 2-Benzylphenol ('''1''') and ] ('''2''') gives 1-benzyl-2-(2-chloropropoxy)benzene ('''3'''). Displacement of the remaining halogen with piperidine completes the synthesis of ''benproperine'' ('''4'''). |
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== References == |
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{{reflist}} |
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{{Cough and cold preparations}} |
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{{Cough and cold preparations}} |
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] |
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{{respiratory-system-drug-stub}} |
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{{respiratory-system-drug-stub}} |
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] |
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