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Pirisudanol

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]

Pirisudanol
Clinical data
AHFS/Drugs.comInternational 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 InfoCard100.046.887 Edit this at Wikidata
Chemical and physical data
FormulaC16H24N2O6
Molar mass340.376 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)

Synthesis

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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

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

See also

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References

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  1. ^ a b "Psycho-Babble Medication Thread 69493".
  2. ^ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
  3. ^ Bathien N, Willer JC, Hugelin A (1976). "[Effect of psychotropic drugs on physiological variations and psychometric scores during attention]". L'Encéphale (in French). 2 (1): 55–60. PMID 1261486.
  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.


 

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