Napactadine (DL-588) is an

antidepressant Antidepressants are a class of medications used to treat major depressive disorder, anxiety disorders, chronic pain, and addiction. Common side effects of antidepressants include Xerostomia, dry mouth, weight gain, dizziness, headaches, akathi ...

which has structural properties that look similar to

PAL-287 Naphthylaminopropane (NAP; code name PAL-287), also known as naphthylisopropylamine (NIPA), is an experimental drug of the amphetamine and naphthylaminopropane families that was under investigation for the treatment of alcohol and stimulant ad ...

methamnetamine Methamnetamine (also known as methylnaphetamine, MNA, MNT, MNAP, PAL-1046, and MY-10) is a triple monoamine releasing agent of the amphetamine and naphthylaminopropane families. It is the ''N''-methyl analog of the non-neurotoxic experimental d ...

, but is based on an

amidine Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2. Examples of amidines includ ...

functional group.

Synthesis

The synthesis of napactadine has been described: Jr James R Mccarthy, US3903163 (1975 to Dow Chemical Co). Napactadine synthesis

Reaction of N-methyl-2-(naphthalen-2-yl)acetamide 086-65-9(1) with triethyloxonium fluoroborate (Meerwein reagent) 68-39-8(2) affords the corresponding imino ether (3). Exposure of this intermediate to

methylamine Methylamine, also known as methanamine, is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold ...

(4) leads to napactidine (5).

References

Amidines 2-Naphthyl compounds Naphthylethylamines {{Nervous-system-drug-stub