Gapicomine

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 It has been withdrawn from the market in the countries it was used in.[1]

Gapicomine
Clinical data
Routes of
administration		By mouth (tablet)
ATC code
  • none
Legal status
Legal status
  • off market (was used in EU countries)
Identifiers
IUPAC name
  • 1-Pyridin-4-yl-N-(pyridin-4-ylmethyl)methanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H13N3
Molar mass199.257 g·mol−1
3D model (JSmol)
SMILES
  • n1ccc(cc1)CNCc2ccncc2
InChI
  • 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
 NY (what is this?)  (verify)

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

History

Gapicomine was discovered in 1970 by Polish chemist Stanisław Biniecki. It was first published about in an article of The Polish Journal of Medicine and Pharmacy describing the derivative drug Bicordin in 1974.[3]

Synthesis
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
  1. "Gapicomine Monograph, The Index Nominum". Retrieved 2008-03-31.
  2. "Bicordin, PubChem". Retrieved 2008-03-31.
  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).


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