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levopropoxyphene
Sign in to saveAlso known as L-propoxyphene, (l)-Propoxyphene, (-)-Propoxyphene
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 (a reversal of Darvon) as an antitussive. Unlike many antitussives, it binds poorly to the sigma-1 receptor.
Chemical data
- Formula
- C22H29NO2
- Molecular weight
- 339.5 g/mol
- IUPAC name
- [(2R,3S)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate
- SMILES
- CCC(=O)O[C@@](CC1=CC=CC=C1)(C2=CC=CC=C2)[C@@H](C)CN(C)C
- InChIKey
- XLMALTXPSGQGBX-PGRDOPGGSA-N
- XLogP
- 4.2
- Polar surface area
- 29.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
5 papers- Three-dimensional view of pharmacology.American journal of hospital pharmacy · 1992
- Reduction of levopropoxyphene N-oxide to propoxyphene by dogs in vivo and rat liver microsomal fraction in vitro.Xenobiotica; the fate of foreign compounds in biological systems · 1977
- High-affinity dextromethorphan binding sites in guinea pig brain. II. Competition experiments.Molecular pharmacology · 1983
- [POISONING BY INGESTION OF AN EXCESSIVE DOSE OF LEVOPROPOXYPHENE (LETUSIN)].Pediatria pratica · 1964
- A NOTE ON THE DIFFERENTIATION BETWEEN DEXTRO- AND LAEVOPROPOXYPHENE.The Journal of pharmacy and pharmacology · 1963
via PubMed
Wikidata facts
- Mass
- 339.21982916800005
Show 5 more facts
- chemical formula
- C₂₂H₂₉NO₂
- canonical SMILES
- CCC(=O)OC(Cc1ccccc1)(c2ccccc2)C(C)CN(C)C
- isomeric SMILES
- CCC(=O)O[C@@](Cc1ccccc1)(c2ccccc2)[C@@H](C)CN(C)C
- subject has role
- antitussive
- Commons category
- Levopropoxyphene
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Synthesis
- Chirality
- References
- See also
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 (a reversal of Darvon) as an antitussive. Unlike many antitussives, it binds poorly to the sigma-1 receptor.
==Synthesis== center|thumb|500x500px|Propoxyphene synthesis Friedel-Crafts acylation of benzene with propionyl chloride and aluminium chloride as a Lewis acid. Mannich reaction of propiophenone with formaldehyde and dimethylamine affords the corresponding aminoketone. 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. Esterification of the alcohol by means of propionic anhydride affords the propionate.
Excerpted from Wikipedia’s “levopropoxyphene” article, available under the CC BY-SA 4.0 licence.
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