Manifaxine

Chemical compound From Wikipedia, the free encyclopedia

Manifaxine (developmental code name GW-320,659) is a norepinephrine–dopamine reuptake inhibitor developed by GlaxoSmithKline through structural modification of radafaxine, an isomer of hydroxybupropion and one of the active metabolites of bupropion.[1] Manifaxine was researched for treatment of attention deficit hyperactivity disorder (ADHD) and obesity and was found to be safe, reasonably effective, and well-tolerated for both applications.[2][3] However, no results were reported following these initial trials and development was discontinued.[1]

Other namesGW-320,659
Routes of
administrationOral
ATC code
  • none
CAS Number
Quick facts Clinical data, Other names ...
Manifaxine
Clinical data
Other namesGW-320,659
Routes of
administration		Oral
ATC code
  • none
Identifiers
  • (2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethylmorpholin-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H15F2NO2
Molar mass243.254 g·mol−1
3D model (JSmol)
  • C[C@@H]1CO[C@]([C@@H](N1)C)(C2=CC(=CC(=C2)F)F)O
  • InChI=1S/C12H15F2NO2/c1-7-6-17-12(16,8(2)15-7)9-3-10(13)5-11(14)4-9/h3-5,7-8,15-16H,6H2,1-2H3/t7-,8+,12-/m1/s1 ☒N
  • Key:OZGPVYJHWWPEFT-RGNHYFCHSA-N ☒N
 ☒NcheckY (what is this?)  (verify)
Close

Synthesis

Synthesis:[4] Patent:[5] See also:[6][7]

The Grignard reaction between 3,5-difluorobenzonitrile (1) and ethylmagnesium bromide gives 3,5-difluoropropiophenone (2). Halogenation with molecular bromine occurs at the alpha-keto position providing 2-bromo-3',5'-difluoropropiophenone (3). Intermolecular ring formation with DL-alaninol (2-aminopropanol) completes the synthesis of manifaxine (4).

See also

References

Related Articles

Wikiwand AI