Delucemine

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Delucemine
Delucemine.png
Systematic (IUPAC) name
3,3-bis(3-fluorophenyl)-N-methylpropan-1-amine
Clinical data
Legal status
?
Identifiers
CAS number 186495-49-8 YesY
ATC code None
PubChem CID 156421
ChemSpider 137745 N
UNII 124LSR3H2X YesY
ChEMBL CHEMBL2106165 N
Chemical data
Formula C16H17F2N 
Molecular mass 261.3097 g/mol
 N (what is this?)  (verify)

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[edit]

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[edit]

  1. ^ NPS Pharmaceuticals Inc NPSP Quarterly Report
  2. ^ Moe, S. T.; Smith, D. L.; By, K.; Egan, J. A.; Filer, C. N. (1998). "Synthesis of 3,3-bis(3-fluorophenyl)-[2,3-3H2]-1-propanamine hydrochloride ([3H2]-NPS 846·HCl): A novel ligand for the NMDA receptor". Journal of Labelled Compounds and Radiopharmaceuticals 41 (6): 535. doi:10.1002/(SICI)1099-1344(199806)41:6<535::AID-JLCR101>3.0.CO;2-P.  edit