gapicomine gapicomine gapicomine (inn) is a coronary vasodilator. it has been withdrawn from the market in the countries it was used in. gapicomineclinical dataroutes ofadministrationby mouth (tablet)atc codenonelegal statuslegal status off market (was used in eu countries) identifiers iupac name 1-pyridin-4-yl-n-(pyridin-4-ylmethyl)methanamine cas number1539-39-5 ypubchem cid68955chemspider62178 nuniiwww0p95393chemblchembl2103958 ncomptox dashboard (epa)dtxsid10165477 chemical and physical dataformulac12h13n3molar mass199.257 g·mol−13d 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 nkey:auqqzpgnrktpsq-uhfffaoysa-n n ny (what is this?) (verify) also, gapicomine is a major component in the drug bicordin. 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. synthesis patent: the oxime formation between isonicotinaldehyde (1) and hydroxylamine gives 4-pyridinealdoxime (2). this is then reduced by catalytic hydrogenation over raney-nickel into 4-picolylamine (3). reductive amination of the last with a second equivalent of isonicotinaldehyde affords gapicomine (4).