Amprolium Chemical Properties

Melting point:

246-248 °C (decomp)

storage temp. 

0-6°C

solubility 

Soluble in DMSO

color 

Crystals from methanol + ethanol

Stability:

Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.

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

InChIKey

LCTXBFGHZLGBNU-UHFFFAOYSA-M

SMILES

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

CAS DataBase Reference

121-25-5(CAS DataBase Reference)

EPA Substance Registry System

Amprolium (121-25-5)

Amprolium Usage And Synthesis

Description

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

Chemical Properties

solid

Originator

Neoprol ,SIMB

Uses

Coccidiostat (for poultry).

Uses

Amprolium is an oral coccidiostat, a thiamine analogue, which is used for the prevention and treatment of intestinal coccidiosis . It is used as a feed additive for livestock, sometimes administered in the food or drinking water of puppies and kittens, and in chickens and calves.

Definition

ChEBI: An organic chloride salt having 1-[(4-amino-2-propylpyrimidin-5-yl)methyl]-2-methylpyridin-1-ium as the counterion. Used for prevention of coccidiosis in poultry and cattle.

Manufacturing Process

1.9 grams of p-toluene sulfonyl chloride was added gradually with shaking to a cooled (0-5°C) solution of 1.67 grams of 2-n-propyl-4-amino-5-hydroxymethyl pyrimidine in 10 ml of 2-methylpyridine. The reaction mixture, after standing three hours in an ice bath, and 15 hours at room temperature, was evaporated to dryness in vacuo. The residue was dissolved in 20 ml of water, acidified with hydrochloric acid and poured over a column of Amberlite IRA- 400 ion exchange resin on the chloride cycle. The eluate was evaporated to dryness to give a residue of 1-(2-n-propyl-4-amino-5-pyrimidylmethyl)-2- methyl pyridinium chloride hydrochloride. On recrystallization from a methanol-ethanol mixture, the quaternary had melting point 246°C (dec.).

brand name

Amprol [Veterinary] (Merial); Amprovine [Veterinary] (Merial); Corid [Veterinary] (Merial).

Therapeutic Function

Coccidiostatic

Contact allergens

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

Side effects

Amprolium is considered one of the safest anticoccidial medications, and adverse reactions such as anorexia or diarrhoea may occur with high doses and prolonged use. Thiamine deficiency can cause central nervous system (CNS) symptoms, but can be reversed with the addition of thiamine to the diet. However, thiamine supplementation may affect the efficacy of the drug.

Safety Profile

When heated to decomposition emits toxic fumes of Cl-.

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