amprolium amprolium amprolium is the organic compound sold as a coccidiostat used in poultry. it has many international nonproprietary names. amprolium names preferred iupac name 1--2-methylpyridin-1-ium chloride other names 1--2-picolinium chloride, amprovine, amprolium, amprol, anticoccid identifiers cas number 121-25-5 n 3d model (jsmol) interactive image chebi chebi:85265 n chembl chembl97350 y chemspider 66070 y echa infocard 100.004.054 ec number 204-458-4 mesh amprolium pubchem cid 2178 unii 71m75t660b n comptox dashboard (epa) dtxsid10904505 inchi inchi=1s/c14h19n4.clh/c1-3-6-13-16-9-12(14(15)17-13)10-18-8-5-4-7-11(18)2;/h4-5,7-9h,3,6,10h2,1-2h3,(h2,15,16,17);1h/q+1;/p-1 ykey: lctxbfghzlgbnu-uhfffaoysa-m yinchi=1/c14h19n4.clh/c1-3-6-13-16-9-12(14(15)17-13)10-18-8-5-4-7-11(18)2;/h4-5,7-9h,3,6,10h2,1-2h3,(h2,15,16,17);1h/q+1;/p-1key: lctxbfghzlgbnu-rewhxwofap smiles .n1c(c(cnc1ccc)c2ccccc2c)n properties chemical formula c14h19n4+ · cl− molar mass 278.780 g·mol−1 pharmacology atcvet code qp51ax09 (who) except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references uses in coccidiosis treatment in poultry the drug is a thiamine analogue and blocks the thiamine transporter of eimeria species. by blocking thiamine uptake it prevents carbohydrate synthesis. despite only moderate efficacy it is well favoured due to few resistance issues and is commonly used in the united states in conjunction with sulfonamides prophylactically in chickens and cattle as a coccidiostat. synthesis amprolium synthesis rogers, sarett, u.s. patent 3,020,277 (1962 to merck & co.), see also u.s. patent 3,020,200 condensation of ethoxymethylenemalononitrile (1) with acetamidine (2) affords the substituted pyrimidine (4). the reaction may well involve conjugate addition of the amidine nitrogen to the malononitrile followed by loss of ethoxide (3); addition of the remaining amidine nitrogen to one of the nitriles will then lead to the pyrimidine (4). reduction of the nitrile gives the corresponding aminomethyl compound (5). exhaustive methylation of the amine followed by displacement of the activated quaternary nitrogen by bromide ion affords the key intermediate (7). displacement of the halogen by α-picoline gives amprolium.