A naphthyl amidine antidepressant.
Pharmaceutical compound
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]
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).
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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