Levopropoxyphene

Levopropoxyphene

Names
IUPAC name (1R,2S)-1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propionate
Other names [(2R,3S)-4-dimethylamino-3-methyl-1,2-diphenyl-butan-2-yl]propanoate
Identifiers
CAS Number	2338-37-6 N
3D model (Jmol)	Interactive image Interactive image
ChEMBL	ChEMBL1213351 N
ChemSpider	21234163 N
PubChem	200742
UNII	U75VZ9PK1J Y
InChI InChI=1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3 N Key: XLMALTXPSGQGBX-UHFFFAOYSA-N N InChI=1/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22-/m1/s1 Key: XLMALTXPSGQGBX-XMSQKQJNBJ
SMILES CCC(=O)OC(Cc1ccccc1)(c2ccccc2)C(C)CN(C)C O=C(O[C@](c1ccccc1)(Cc2ccccc2)[C@@H](C)CN(C)C)CC
Properties
Chemical formula	C22H29NO2
Molar mass	339.471
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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.

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.