Pirisudanol Explained

Pirisudanol (Mentis, Menthen, Mentium, Nadex, Nadexen, Nadexon, Pridana, Stivane), also known as pyrisuccideanol, is the succinic acid ester of pyridoxine (a form of vitamin B₆) and of deanol (DMAE).^[1] It has been used in Europe in the treatment of mild cognitive impairment as well as fatigue and depression.^{[1] [2] [3] [4] [5]}

Synthesis

Pirisudanol is synthesized by the following method:^{[6] [7]} Cyclic ketal formation between pyridoxime [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).

Analytical data

(uv, ir, pmr, ms):^[8]

See also

• Pyritinol

Notes and References

1. Web site: Psycho-Babble Medication Thread 69493 .
2. Book: David J. Triggle . Dictionary of Pharmacological Agents . Chapman & Hall/CRC . Boca Raton . 1996 . 0-412-46630-9 .
3. Bathien N, Willer JC, Hugelin A . [Effect of psychotropic drugs on physiological variations and psychometric scores during attention] . fr . L'Encéphale . 2 . 1 . 55–60 . 1976 . 1261486 .
4. Murphy JE . An evaluation of pyrisuccideanol maleate (Nadex) in the treatment of mild to moderate depression in patients aged 55 years and over, presenting in general practice . The Journal of International Medical Research . 9 . 5 . 330–7 . 1981 . 7297757 . 10.1177/030006058100900506. 30526982 .
5. Zmorski T . [Experience with Nadex in an ambulatory psychiatric practice] . de . Therapeutische Umschau. Revue Thérapeutique . 40 . 9 . 817–20 . September 1983 . 6138876 .
6. Andre Paris Esanu, DE2102831B2 (1975 to Societe D'etudes De Produits, Chimiques, Issy-Les-Moulineaux (Frankreich)).
7. Andre Esanu, GB1447338 (1976 to Soc D Etudes Prod Chimique).
8. Gielsdorf, W.; Klug, E. (1983). "Zur Analytik und renalem Ausscheidungsverhalten von Pirisudanol (Stivane)". Zeitschrift für Rechtsmedizin. 90 (3): 229–238. doi:10.1007/BF02116234. ISSN 0044-3433.