Pirisudanol

Pirisudanol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N06BX08 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 2-(dimethylamino)ethyl[5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridinyl]methylbutanedioate;
CAS Number	33605-94-6 ;
PubChem CID	65782;
ChemSpider	59202;
UNII	W618Z2SMVL;
KEGG	D07347 ;
CompTox Dashboard (EPA)	DTXSID60187301 ;
ECHA InfoCard	100.046.887
Chemical and physical data
Formula	C16H24N2O6
Molar mass	340.376 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=NC=C(C(=C1O)CO)COC(=O)CCC(=O)OCCN(C)C;
	InChI 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]

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]

References

^ ^a ^b "Psycho-Babble Medication Thread 69493".
^ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
^ 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.
^ 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.
^ Zmorski T (September 1983). "[Experience with Nadex in an ambulatory psychiatric practice]". Therapeutische Umschau. Revue Thérapeutique (in German). 40 (9): 817–20. PMID 6138876.
^ Andre Paris Esanu, DE2102831B2 (1975 to Societe D'etudes De Produits, Chimiques, Issy-Les-Moulineaux (Frankreich)).
^ Andre Esanu, GB1447338 (1976 to Soc D Etudes Prod Chimique).
^ 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.

[urlPsycho-Babble_Medication_Thread_69493-1] "Psycho-Babble Medication Thread 69493".

[isbn0-412-46630-9-2] David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.

[pmid1261486-3] 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.

[pmid7297757-4] 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.

[pmid6138876-5] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

Synthesis

Analytical data

See also

References