Gapicomine

Chemical compound
  • none
Legal statusLegal status
  • off market (was used in EU countries)
Identifiers
  • 1-Pyridin-4-yl-N-(pyridin-4-ylmethyl)methanamine
CAS Number
  • 1539-39-5 checkY
PubChem CID
  • 68955
ChemSpider
  • 62178 ☒N
UNII
  • WWW0P95393
ChEMBL
  • ChEMBL2103958 ☒N
CompTox Dashboard (EPA)
  • DTXSID10165477 Edit this at Wikidata
Chemical and physical dataFormulaC12H13N3Molar mass199.257 g·mol−13D model (JSmol)
  • Interactive image
  • 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
 ☒NcheckY (what is this?)  (verify)

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 It has been withdrawn from the market in the countries it was used in.[1]

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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