Amprolium Hydrochloride Chemical Properties

Melting point:

239.0 to 243.0 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Methanol (Slightly), Water (Slightly)

form 

Powder

color 

White to Off-white

BRN 

4118699

InChI

InChI=1S/C14H19N4.2ClH/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);2*1H/q+1;;/p-1

InChIKey

PJBQYZZKGNOKNJ-UHFFFAOYSA-M

SMILES

C1(C=NC(CCC)=NC=1N)C[N+]1C=CC=CC=1C.Cl.[Cl-]

CAS DataBase Reference

137-88-2(CAS DataBase Reference)

EPA Substance Registry System

Amprolium hydrochloride (137-88-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

TJ7565000

HS Code 

29335995

MSDS

• Language:English Provider:SigmaAldrich

Amprolium Hydrochloride Usage And Synthesis

Description

Amprolium is a thiamine analog and antiprotozoal agent that interferes with thiamine metabolism and inhibits carbohydrate synthesis. It competitively inhibits thiamine uptake by E. tenella schizonts and by chick host intestinal cells (K_is = 7.6 and 326 μM, respectively). It also inhibits hexose formation and pentose utilization ex vivo in isolated lysed rat erythrocytes and in liver, kidney, heart, and intestinal tissue homogenates following dietary administration. Amprolium (1,000 ppm in feed) inhibits oocyst output and sporulation of Eimeria maxima, E. brunetti, and E. acervulina in infected chicks. It also decreases lesion and oocyst scores and mortality of E. tenella-infected chicks following dietary administration of a 125 ppm dose. Amprolium (100 μM) induces apoptosis in PC12 rat adrenal cells and increases the level of cleaved caspase-3. Formulations containing amprolium have been used as coccidiostats in poultry processing.

Chemical Properties

Crystalline powder

Uses

Coccidiostatic;Thiamine transport inhibitor

Uses

Thiamine analog coccidiostat.

Uses

1-(4-Amino-2-n-propyl-5-pyrimidinylmethyl)-2-methylpyridinium Chloride is an antiparasytic drug used in the veterinary industry. In addition the compound shows anticoccidial activity.

Definition

MeSH: Amprolium Hydrochloride is a veterinary coccidiostat that interferes with thiamine metabolism.

Contact allergens

Amprolium is an antiprotozoal agent used for the prevention of coccidiosis in poultry.

Veterinary Drugs and Treatments

Amprolium has good activity against Eimeria tenella and E. acervulina in poultry and can be used as a therapeutic agent for these organisms. It only has marginal activity or weak activity against E. maxima, E. mivati, E. necatrix, or E. brunetti. It is often used in combination with other agents (e.g., ethopabate) to improve control against those organisms.
In cattle, amprolium has approval for the treatment and prevention of E. bovis and E. zurnii in cattle and calves.
Amprolium has been used in dogs, swine, sheep, and goats for the control of coccidiosis, although there are no approved products in the USA for these species.

References

[1] JAMES S. Thiamine uptake in isolated schizonts of Eimeria tenella and the inhibitory effects of amprolium.[J]. Parasitology, 1980, 80 2: 313-322. DOI: 10.1017/s0031182000000779
[2] BRIN M. The antithiamine effects of amprolium in rats on tissue transketolase activity[J]. Toxicology and applied pharmacology, 1964, 6 4: Pages 454-458. DOI: 10.1016/s0041-008x(64)80012-0
[3] L P JOYNER  C C N. The anticoccidial effects of amprolium, dinitolmide and monensin against Eimeria maxima, E, brunetti and E. acervulina with particular reference to oocyst sporulation.[J]. Parasitology, 1977, 75 2: 155-164. DOI: 10.1017/s0031182000062296
[4] R. Z. ABBAS. Anticoccidial activity of hydrochloric acid (HCl) against Eimeria tenella in broiler chickens[J]. Pesquisa Veterinaria Brasileira, 2011, 11 1: 425-429. DOI: 10.1590/s0100-736x2011000500010
[5] S. CHORNYY N C J Parkhomenko. Thiamine deficiency caused by thiamine antagonists triggers upregulation of apoptosis inducing factor gene expression and leads to caspase 3-mediated apoptosis in neuronally differentiated rat PC-12 cells.[J]. Acta biochimica Polonica, 2007, 54 2 1: 315-322. DOI: 10.18388/abp.2007_3252

Amprolium Hydrochloride(137-88-2)Related Product Information

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• Amprolium Hydrochloride
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• 4-Pyrimidinamine, 2,5-dimethyl- (9CI)
• 5-Pyrimidinemethanamine, 2-methyl- (9CI)
• 4-Amino-5-aminomethyl-2-methylpyrimidine