Delucemine

Delucemine

Systematic (IUPAC) name
3,3-bis(3-fluorophenyl)-N-methylpropan-1-amine
Clinical data
Identifiers
CAS Registry Number	186495-49-8 Y
ATC code	None
PubChem	CID 156421
ChemSpider	137745 N
UNII	124LSR3H2X Y
ChEMBL	CHEMBL2106165 N
Chemical data
Formula	C16H17F2N
Molecular mass	261.3097 g/mol
SMILES CNCCC(C1=CC(=CC=C1)F)C2=CC(=CC=C2)F
InChI InChI=1S/C16H17F2N/c1-19-9-8-16(12-4-2-6-14(17)10-12)13-5-3-7-15(18)11-13/h2-7,10-11,16,19H,8-9H2,1H3  N Key:MUGNLPWYHGOJEG-UHFFFAOYSA-N  N
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

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.

See also

• Gamfexine

References

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.