Dextromethadone

Dextromethadone
Names
IUPAC name
(6S)-6-(Dimethylamino)-4,4-diphenylheptan-3-one
Other names
d-Methadone; 6S-Methadone; (+)-Methadone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.164.915
Properties
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 the (S)-enantiomer of methadone. Dextromethadone acts as a N-methyl-D-aspartate NMDA receptor antagonist. [1]

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

See also

References

  1. Gorman AL, Elliott KJ, Inturrisi CE (Feb 14, 1997). "The d- and l-isomers of methadone bind to the non-competitive site on the N-methyl-D-aspartate (NMDA) receptor in rat forebrain and spinal cord". Neurosci Letter. 223 (1): 5–8. PMID 9058409.
  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



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