Amprolium

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Amprolium
Amprolium.svg
Names
IUPAC name
5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propyl-pyrimidin-4-amine chloride
Other names
1-[(4-Amino-2-propyl-5-pyrimidinyl)methyl]-2-picolinium chloride
Identifiers
ATCvet code QP51AX09
137-88-2 N
ChEBI CHEBI:85265 N
ChEMBL ChEMBL97350 YesY
ChemSpider 66070 YesY
EC number 204-458-4
Jmol-3D images Image
MeSH Amprolium
PubChem 2178
Properties
C14H19N4+ · Cl
Molar mass 278.780 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Amprolium (INN, trade names Amprovine, Amprolium, Amprol, Anticoccid) is a coccidiostat used 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 conjunction with sulfonamides prophylactically in chickens and cattle as a coccidiostat.

Synthesis[edit]

Coccidia are protozoans that can wreak havoc in a flock of poultry by an infection known as coccidiosis. Agents that control this disease–coccidiostats–are in view of the world's heavy dependence on poultry as a source of protein, of great economical significance.

Amprolium synthesis:[1][2] Rogers, Sarett, U.S. Patent 3,020,277 (1962 to Merck & Co.), see also U.S. Patent 3,020,200 [3]

Condensation of ethoxymethylenemalononitrile (1) with acetamidine (2) affords the substituted pyrimidine (4). The rxn 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 amin 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.

References[edit]

  1. ^ Sarett, Lewis H. (1960). "The hormones". Journal of Chemical Education 37 (4): 184. doi:10.1021/ed037p184. 
  2. ^ Grewe, R. Z. Physiol. Chem. (1936).
  3. ^ http://www.dissertationtopic.net/doc/1133386