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| Names | |
|---|---|
| Preferred IUPAC name (2R,3S)-4-(Dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
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| UNII | |
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| Properties | |
| C22H29NO2 | |
| Molar mass | 339.471 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Levopropoxyphene is anantitussive. It is anoptical isomer ofdextropropoxyphene. Theracemic mixture is calledpropoxyphene. 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 tradenameNovrad (a reversal ofDarvon) as an antitussive.[1][2] Unlike many antitussives, it binds poorly to thesigma-1 receptor.[3]
The presence of two chiral centers in this molecule means that the compound can exist as any of four isomers. 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 usefulantitussive activity and is named levopropoxyphene.[citation needed]
