Pirisudanol (Mentis, Menthen, Mentium, Nadex, Nadexen, Nadexon, Pridana, Stivane), also known as pyrisuccideanol, is the succinic acid ester of pyridoxine (a form of vitamin B<sub>6</sub>) and of deanol (DMAE). It has been used in Europe in the treatment of mild cognitive impairment as well as fatigue and depression.
Pirisudanol is synthesized by the following method:
Cyclic ketal formation between pyridoxine [33605-94-6] HCl: [58-56-0] (1) and acetone resulted in alpha4,3-O-Isopropylidene Pyridoxine [1136-52-3] (2). In the other arm of the synthesis succinic anhydride [108-30-5] (3) is then esterified with Deanol [108-01-0] (4) gives Yakton [10549-59-4] (5). Halogenation of the remaining carboxyl group with thionyl chloride gives PC135056269 (6). In a convergent synthesis, esterification between 2 and 6 gives 7. The last step consists of deblocking the protecting group by hydrolysis with 1% formic acid in ethanol to give the product (8).
(uv, ir, pmr, ms):