Napactadine

Napactadine (DL-588) is an antidepressant which has structural properties that look similar to PAL-287 or methamnetamine, but is based on an amidine functional group.^[1]

Napactadine

Clinical data
Other names	DL-588
Identifiers
IUPAC name N,N'-dimethyl-2-naphthalen-2-ylethanimidamide
CAS Number	76631-45-3
PubChem CID	42153
ChemSpider	38442
UNII	571S87U90N
ChEMBL	ChEMBL1192539
Chemical and physical data
Formula	C14H16N2
Molar mass	212.296 g·mol−1
3D model (JSmol)	Interactive image
SMILES CNC(=NC)CC1=CC2=CC=CC=C2C=C1
InChI InChI=1S/C14H16N2/c1-15-14(16-2)10-11-7-8-12-5-3-4-6-13(12)9-11/h3-9H,10H2,1-2H3,(H,15,16) Key:NAHCWQNNENHGNH-UHFFFAOYSA-N

Synthesis

The synthesis of napactadine has been described:^[2][3]

Napactadine synthesis

Reaction of N-methyl-2-(naphthalen-2-yl)acetamide [2086-65-9] (1) with triethyloxonium fluoroborate (Meerwein reagent) [368-39-8] (2) affords the corresponding imino ether (3). Exposure of this intermediate to methylamine (4) leads to napactidine (5).