Levopropoxyphene

Levopropoxyphene
Names
	Preferred IUPAC name (2R,3S)-4-(Dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate
Identifiers
CAS Number	2338-37-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL1213351 ;
ChemSpider	21234163 ;
PubChem CID	200742;
UNII	U75VZ9PK1J ;
CompTox Dashboard (EPA)	DTXSID8023212 ;
	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 Key: XLMALTXPSGQGBX-UHFFFAOYSA-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). verify (what is ?) 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.^[1]^[2] Unlike many antitussives, it binds poorly to the sigma-1 receptor.^[3]

^ Reference.MD: Propoxyphene napsylate
^ Lutje Spelberg, Jeffrey Harald (2003). Enantioselective biocatalytic conversions of epoxides. Rijksuniversiteit Groningen.
^ Klein M, Musacchio JM (October 10, 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–156. doi:10.1007/BF00711241. PMC 11567495. PMID 3044591. S2CID 33844132.

[1] Reference.MD: Propoxyphene napsylate

[2] Lutje Spelberg, Jeffrey Harald (2003). Enantioselective biocatalytic conversions of epoxides. Rijksuniversiteit Groningen.

[3] Klein M, Musacchio JM (October 10, 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–156. doi:10.1007/BF00711241. PMC 11567495. PMID 3044591. S2CID 33844132.

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