Delucemine

Delucemine

Delucemine
Systematic (IUPAC) name
3,3-bis(3-fluorophenyl)-N-methylpropan-1-amine
Clinical data
Legal status
?
Identifiers
CAS number
ATC code None
PubChem
ChemSpider
UNII  YesY
ChEMBL
Chemical data
Formula C16H17F2N 
Mol. mass 261.3097 g/mol
 YesY   

Delucemine (NPS-1506) is a drug which acts as an NMDA antagonist and a serotonin reuptake inhibitor, and has neuroprotective effects. It was originally investigated for the treatment of stroke but is now being studied as a potential antidepressant. It is currently in clinical trials.[1]

Synthesis

Delucemine synthesis:[2]

Condensation of 3,3-difluorobenzophenone with the lithio reagent from acetonitrile yields the benzydrol. The nitrile group is then reduced to the corresponding amine by means of diborane. Treatment with acid leads to loss of the tertiary hydroxyl group and formation of the olefin. The double bond is reduced by catalytic hydrogenation. The primary amino group can then be converted to the N-methyl derivative by any of a number of procedures, such as, treatment with formaldehyde and formic acid. Then the NMDA receptor antagonist delucemine is obtained.

References

  1. ^ NPS Pharmaceuticals Inc NPSP Quarterly Report
  2. ^ S.T. Moe, D.L. Smith, K. By, J.A. Egan, C.N. Filer, J. Label. Comp. Radiopharm. 41, 535 (1998).