World Library  
Flag as Inappropriate
Email this Article


Article Id: WHEBN0004139139
Reproduction Date:

Title: Levopropoxyphene  
Author: World Heritage Encyclopedia
Language: English
Subject: List of opioids, List of compounds with carbon number 22, Antitussives, Mucokinetics, Isoaminile
Publisher: World Heritage Encyclopedia


CAS number  N
ChemSpider  N
Jmol-3D images Image 1
Image 3
Molecular formula C22H29NO2
Molar mass 339.47 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Levopropoxyphene is an antitussive. It is an optical isomer of dextropropoxyphene. The racemic mixture is called propoxyphene. Only the dextro-isomer (dextropropoxyphene) has an analgesic effect; the levo-isomer appears to exert only an antitussive effect. It was formerly marketed in the U.S. by Eli Lilly under the tradename Novrad as an antitussive.[1][2]


Propoxyphene synthesis[3]
  1. Mannich reaction of propiophenone with formaldehyde and dimethylamine affords the corresponding aminoketone.
  2. Reaction of the ketone with benzylmagnesium bromide gives the amino alcohol. It is of note that this intermediate fails to show analgesic activity in animal assays.
  3. Esterification of the alcohol by means of propionic anhydride affords the propionate.[4]


The presence of two chiral centers in this molecule means, of course, that the compound will exist as two racemic pairs. The biologic activity has been found to be associated with the α isomer. Resolution of that isomer into its optical antipodes showed the d isomer to be the active analgesic; this is now denoted as propoxyphene. The l isomer is almost devoid of analgesic activity; the compound does, however, show useful antitussive activity and is named levopropoxyphene.


  1. ^ Reference.MD: Propoxyphene napsylate
  2. ^ Lutje Spelberg; Jeffrey Harald (2003). "Enantioselective biocatalytic conversions of epoxides". Rijksuniversiteit Groningen. 
  3. ^ Chenier, Philip J. (2002) Survey of Industrial Chemistry. Springer. ISBN 0306472465. p. 455.
  4. ^ Pohland, A.; Sullivan, H. R. (1953). "Analgesics: Esters of 4-Dialkylamino-1,2-diphenyl-2-butanols". Journal of the American Chemical Society 75 (18): 4458–4461.  

This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.

Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.