Structure via PubChem · Public domain (PubChem)
pirisudanol
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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). It has been used in Europe in the treatment of mild cognitive impairment as well as fatigue and depression. ==Synthesis== Pirisudanol is synthesized by the following method: class=skin-invert-image|center|500px 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 suc
In the Vinony graph
Vinony's link graph records 570 inbound references to pirisudanol, and connects out to atropine, tricyclic antidepressant and nicotinic acetylcholine receptor.
Vinony files it under Antidepressants, Chemical pages without DrugBank identifier and Cholinergics.
Vinony links it to 5 Wikipedia language editions.
Chemical data
- Formula
- C16H24N2O6
- Molecular weight
- 340.37 g/mol
- IUPAC name
- 1-O-[2-(dimethylamino)ethyl] 4-O-[[5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridinyl]methyl] butanedioate
- SMILES
- CC1=NC=C(C(=C1O)CO)COC(=O)CCC(=O)OCCN(C)C
- InChIKey
- KTOAWCPDBUCJED-UHFFFAOYSA-N
- XLogP
- -0.4
- Polar surface area
- 109 Ų
- H-bond donors
- 2
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- attention deficit hyperactivity disorder
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 340.163
Show 4 more facts
- chemical formula
- C₁₆H₂₄N₂O₆
- canonical SMILES
- CC1=NC=C(C(=C1O)CO)COC(=O)CCC(=O)OCCN(C)C
- World Health Organisation international non-proprietary name
- pirisudanol
- subject has role
- nootropic
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Synthesis
- Analytical data
- See also
- References
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). It has been used in Europe in the treatment of mild cognitive impairment as well as fatigue and depression. ==Synthesis== Pirisudanol is synthesized by the following method: class=skin-invert-image|center|500px 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).
==Analytical data== (uv, ir, pmr, ms): == See also == Pyritinol
Excerpted from Wikipedia’s “pirisudanol” article, available under the CC BY-SA 4.0 licence.