Napactadine

Napactadine
Clinical data
Other names	DL-588
Identifiers
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;

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

Synthesis

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

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

^ Castañer J, Hillier K (1981). "DL-588". Drugs of the Future. 6 (6): 348. doi:10.1358/dof.1981.006.06.1003976.
^ McCarthy JR, Wright DL, Schuster AJ, Abdallah AH, Shea PJ, Eyster R (November 1985). "New bicyclic antidepressant agent. Synthesis and activity of napactadine and related compounds". Journal of Medicinal Chemistry. 28 (11): 1721–7. doi:10.1021/jm00149a031. PMID 4067998.
^ Jr James R Mccarthy, US3903163 (1975 to Dow Chemical Co).

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[1] Castañer J, Hillier K (1981). "DL-588". Drugs of the Future. 6 (6): 348. doi:10.1358/dof.1981.006.06.1003976.

[pmid4067998-2] McCarthy JR, Wright DL, Schuster AJ, Abdallah AH, Shea PJ, Eyster R (November 1985). "New bicyclic antidepressant agent. Synthesis and activity of napactadine and related compounds". Journal of Medicinal Chemistry. 28 (11): 1721–7. doi:10.1021/jm00149a031. PMID 4067998.

[3] Jr James R Mccarthy, US3903163 (1975 to Dow Chemical Co).

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