Amprolium

Amprolium
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, Amprovine, Amprolium, Amprol, Anticoccid
Identifiers
CAS Number	121-25-5 [correct];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:85265 ;
ChEMBL	ChEMBL97350 ;
ChemSpider	66070 ;
ECHA InfoCard	100.004.054
EC Number	204-458-4;
MeSH	Amprolium
PubChem CID	2178;
UNII	71M75T660B ;
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 Key: LCTXBFGHZLGBNU-UHFFFAOYSA-M ; InChI=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-1 Key: LCTXBFGHZLGBNU-REWHXWOFAP;
	SMILES [Cl-].n1c(c(cnc1CCC)C[n+]2ccccc2C)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 [77 °F], 100 kPa).
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	Infobox references

Amprolium is the organic compound sold as a coccidiostat used in poultry. It has many International Nonproprietary Names.[1]

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.

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

Production

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 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.

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References

Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.
Grewe, R. Z. Physiol. Chem. (1936).
"Archived copy". Archived from the original on 2015-04-02. Retrieved 2015-03-30.CS1 maint: archived copy as title (link)

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[Ullmann-1] Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.

[2] Grewe, R. Z. Physiol. Chem. (1936).

[3] "Archived copy". Archived from the original on 2015-04-02. Retrieved 2015-03-30.CS1 maint: archived copy as title (link)