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Gapicomine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Gapicomine
Clinical data
Routes of
administration
By mouth (tablet)
ATC code
  • none
Legal status
Legal status
  • off market (was used in EU countries)
Identifiers
  • 1-Pyridin-4-yl-N-(pyridin-4-ylmethyl)methanamine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC12H13N3
Molar mass199.257 g·mol−1
3D model (JSmol)
  • n1ccc(cc1)CNCc2ccncc2
  • InChI=1S/C12H13N3/c1-5-13-6-2-11(1)9-15-10-12-3-7-14-8-4-12/h1-8,15H,9-10H2 ☒N
  • Key:AUQQZPGNRKTPSQ-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Gapicomine (INN) is acoronaryvasodilator. It has been withdrawn from the market in the countries it was used in.[1]

Also, gapicomine is a major component in the drugBicordin.[2]

History

[edit]

Gapicomine was discovered in 1970 byPolishchemistStanisław Biniecki. It was first published about in an article ofThe Polish Journal of Medicine and Pharmacy describing the derivative drugBicordin in 1974.[3]

Synthesis

[edit]
Patent:[4]

The oxime formation between isonicotinaldehyde [872-85-5] (1) and hydroxylamine gives 4-Pyridinealdoxime [696-54-8] (2). This is then reduced by catalytic hydrogenation over Raney-Nickel into 4-Picolylamine [3731-53-1] (3). Reductive amination of the last with a second equivalent of isonicotinaldehyde affords gapicomine (4).

References

[edit]
  1. ^"Gapicomine Monograph, The Index Nominum". Retrieved2008-03-31.
  2. ^"Bicordin, PubChem". Retrieved2008-03-31.
  3. ^Samochowiec L, Wójcicki J, Gregorczyk K, Szmatloch E (1974). "Bicordin--a new drug in the treatment of coronary heart disease".Mater Med Pol.6 (4):298–300.PMID 4453155.
  4. ^Anon.,GB 1058356  (1967 to Starogardzkie Zakl Farma).
Nitrovasodilators
Quinolone vasodilators
Others
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