ChemicalBook--->CAS DataBase List--->137-88-2

137-88-2

137-88-2 Structure

137-88-2 Structure
IdentificationMore
[Name]

1-([4-Amino-2-propyl-5-pyrimidinyl]methyl)-2-methylpyridinium chloride
[CAS]

137-88-2
[Synonyms]

1-([4-AMINO-2-PROPYL-5-PYRIMIDINYL]METHYL)-2-METHYLPYRIDINIUM CHLORIDE
1-[(4-AMINO-2-PROPYL-5-PYRIMIDINYL)-METHYL]-2-METHYLPYRIDINIUM CHLORIDE HYDROCHLORIDE
5-[(6-METHYLPYRIDIN-1-YL)METHYL]-2-PROPYL-PYRIMIDIN-4-AMINE CHLORIDE HYDROCHLORIDE
AMPROLIUM HCL
AMPROLIUM HYDROCHLORIDE
2-picolinium,1-((4-amino-2-propyl-5-pyrimidinyl)methyl)-,chloride,monohydroc
amprol
amprol25
amprol25percent
mepyrium
pyridinium,1-((4-amino-2-propyl-5-pyrimidinyl)methyl)-2-methyl-,chloride,m
1-(4-amino-2-propylpyrimidin-5-ylmethyl)-2-methylpyridinium chloride hydrochloride
AMPROLIUM HYDROCHLORIDE VETRANAL, 250
AmproliumHclUsp27
Pyridinium, 1-(4-amino-2-propyl-5-pyrimidinyl)methyl-2-methyl-, chloride, monohydrochloride
thiacoccid
1-([4-Amino-2-propyl-5-pyrimidinyl]methyl)-2-methylpyridinium chloride
[EINECS(EC#)]

205-307-5
[Molecular Formula]

C14H20Cl2N4
[MDL Number]

MFCD00078831
[Molecular Weight]

315.24
[MOL File]

137-88-2.mol
Chemical PropertiesBack Directory
[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
[Contact allergens]

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

137-88-2(EPA Substance)
Hazard InformationBack Directory
[Chemical Properties]

Crystalline powder
[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.
[Uses]

Coccidiostatic;Thiamine transport inhibitor
[Uses]

Thiamine analog coccidiostat.
[Description]

Amprolium(137-88-2) 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 (Kis = 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.
[Definition]

MeSH: Amprolium Hydrochloride is a veterinary coccidiostat that interferes with thiamine metabolism.
[Veterinary Drugs and Treatments]

Amprolium(137-88-2) 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.
[storage]

Store at -20°C
[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
Safety DataBack Directory
[Symbol(GHS) ]

Health Hazard (GHS08)
GHS08
[Signal word ]

Danger
[Hazard statements ]

H317-H334
[Precautionary statements ]

P261-P272-P280-P284-P302+P352-P333+P313
[Hazard Codes ]

Xn
[Risk Statements ]

R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

3
[RTECS ]

TJ7565000
[HS Code ]

29335990
Spectrum DetailBack Directory
[Spectrum Detail]

Amprolium Hydrochloride(137-88-2)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

137-88-2(sigmaaldrich)
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