Pirisudanol

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Pirisudanol
Pirisudanol.png
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 2-(dimethylamino)ethyl[5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridinyl]methylbutanedioate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.046.887 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H24N2O6
Molar mass 340.376 g·mol−1
3D model (JSmol)
  • CC1=NC=C(C(=C1O)CO)COC(=O)CCC(=O)OCCN(C)C
  • InChI=1S/C16H24N2O6/c1-11-16(22)13(9-19)12(8-17-11)10-24-15(21)5-4-14(20)23-7-6-18(2)3/h8,19,22H,4-7,9-10H2,1-3H3
  • Key:KTOAWCPDBUCJED-UHFFFAOYSA-N
   (verify)

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]

Contents

Synthesis

Pirisudanol is synthesized by the following method: [6] [7]

Pirisudanol synthesis.svg

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

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References

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  4. Murphy JE (1981). "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. doi:10.1177/030006058100900506. PMID   7297757. S2CID   30526982.
  5. Zmorski T (September 1983). "[Experience with Nadex in an ambulatory psychiatric practice]". Therapeutische Umschau. Revue Thérapeutique (in German). 40 (9): 817–20. PMID   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.