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 It has been withdrawn from the market in the countries it was used in.^[1]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	1539-39-5 Y
PubChem CID	68955
ChemSpider	62178 N
UNII	WWW0P95393
ChEMBL	ChEMBL2103958 N
CompTox Dashboard (EPA)	DTXSID10165477
Chemical and physical data
Formula	C12H13N3
Molar mass	199.257 g·mol−1
3D model (JSmol)	Interactive image
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).