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
Identifiers
CAS Number	137-88-2
ChEBI	CHEBI:85265
ChEMBL	ChEMBL97350
ChemSpider	66070
EC Number	204-458-4
Jmol interactive 3D	Image
MeSH	Amprolium
PubChem	2178
UNII	71M75T660B
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
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 (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

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

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