Dextromethadone

Dextromethadone

Names
IUPAC name (6S)-6-(Dimethylamino)-4,4-diphenylheptan-3-one
Other names d-Methadone; 6S-Methadone; (+)-Methadone
Identifiers
CAS Number	5653-80-5
ChemSpider	559067
Jmol interactive 3D	Image
PubChem	643985
InChI InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3/t17-/m0/s1 Key: USSIQXCVUWKGNF-KRWDZBQOSA-N
SMILES CCC(=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
Properties
Chemical formula	C21H27NO
Molar mass	309.45 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dextromethadone is an antitussive opioid.^[1] It is the (S)-enantiomer of methadone.

There is now an asymmetric synthesis^[2] available to prepare both dextromethadone [S-(+)-methadone] and levomethadone [R-(−)-methadone].^[3]

See also

• Levomethadone

References

1. Rasch, M (1957). "Dextromethadone and its antitussive effect". Nordisk medicin 57 (17): 629–31. PMID 13441112.
2. Hull JD, Scheinmann F, Turner NJ, (March 2003). "Synthesis of optically active methadones, LAAM and bufuralol by lipase-catalysed acylations". Tetrahedron: Asymmetry 14 (5): 567–576. doi:10.1016/S0957-4166(03)00019-3.
3. US patent 6143933