Napactadine

Antidepressant drug From Wikipedia, the free encyclopedia

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]

Other namesDL-588
CAS Number
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Quick facts Clinical data, Other names ...
Napactadine
Clinical data
Other namesDL-588
Identifiers
  • N,N'-dimethyl-2-naphthalen-2-ylethanimidamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC14H16N2
Molar mass212.296 g·mol−1
3D model (JSmol)
  • CNC(=NC)CC1=CC2=CC=CC=C2C=C1
  • 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
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Synthesis

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

Napactadine synthesis
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).

References

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