Amprolium Hydrochloride

Iupac Name：5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine;chloride;hydrochloride

Molecular Weight：315.24

Modify Date.: 2022-11-01 23:22

Introduction: Thiamine analog coccidiostat.Used as an anticoccidial drug, it is effective against Eimeria in chickens, Eimeria acervulina, lamb and calves. Anti-coccidiosis. View more+

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1. Names and Identifiers

1.1 Name: Amprolium Hydrochloride
1.2 Synonyms: 1-[(4-Amino-2-propyl-5-pyrimidinyl)methyl]-2-methylpyridinium Chloride Hydrochloride 2-picolinium,1-((4-amino-2-propyl-5-pyrimidinyl)methyl)-,chloride,monohydroc 5-[(6-METHYLPYRIDIN-1-YL)METHYL]-2-PROPYL-PYRIMIDIN-4-AMINE CHLORIDE HYDROCHLORIDE amprol amprol25 amprol25percent Amprolium (hydrochloride) AMPROLIUM HCL AMPROLIUM HYDROCHLORIDE VETRANAL,250 AmproliumHclUsp27 EINECS 205-307-5 mepyrium MFCD00078831 pyridinium,1-((4-amino-2-propyl-5-pyrimidinyl)methyl)-2-methyl-,chloride,m thiacoccid Thiacoccide

1.3 CAS No.: 137-88-2

1.4 CID: 8732

1.5 EINECS(EC#): 205-307-5; 204-458-4

1.6 Molecular Formula: C14H20Cl2N4 (isomer)

1.7 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

1.8 InChkey: PJBQYZZKGNOKNJ-UHFFFAOYSA-M

1.9 Canonical Smiles: CCCC1=NC=C(C(=N1)N)C[N+]2=CC=CC=C2C.Cl.[Cl-]

1.10 Isomers Smiles: CCCC1=NC=C(C(=N1)N)C[N+]2=CC=CC=C2C.Cl.[Cl-]

2. Properties

2.1 Melting point: 239.0 to 243.0 °C

2.1 Boiling point: °Cat760mmHg

2.1 Flash Point: °C

2.1 Precise Quality: 314.10700

2.1 PSA: 55.68000

2.1 logP: 0.04270

2.1 Appearance: Faint yellow to off white powder

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: Crystalline powder

2.4 Color/Form: White to Off-white

2.5 Contact Allergens: Amprolium is an antiprotozoal agent used for the preventionof coccidiosis in poultry.

2.6 Water Solubility: Soluble in water (200 mg/ 4 ml - clear, yellow solution)

2.7 StorageTemp: Inert atmosphere,Room Temperature

3. Use and Manufacturing

3.1 Usage: Coccidiostatic;Thiamine transport inhibitor

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: 20/21/22-36/37/38

4.1 Safety Statements: 22-24/25-36-26

4.1 RIDADR: NONH for all modes of transport

4.1 WGK Germany: 3

4.1 RTECS: TJ7565000

4.1 Safety: Safety Information of Amprolium hydrochloride (CAS NO.137-88-2):
Hazard Codes:?Xn
Risk Statements: 20/21/22-36/37/38
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 22-24/25-36-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany: 3
RTECS: TJ7565000

4.2 Specification: ? Amprolium hydrochloride , with CAS number of 137-88-2, can be called 2-Picolinium, 1-[ (4-amino-2-propyl-5-pyrimidinyl)methyl]-, chloride, monohydrochloride ; Thiacoccid ; 2-Picolinium, 1-((4-amino-2-propyl-5-pyrimidinyl)methyl)-, chloride, monohydrochloride ; Pyridinium,1-[(4-amino-2-propyl-5- pyrimidinyl)methyl]-2-methyl-, chloride,monohydrochloride ; 1-[(4-Amino-2-propylpyrimidin-5-yl)methyl]-2-methylpyridinium chloride hydrochloride (1:1:1) ; Pyridinium, 1-[ (4-amino-2-propyl-5-pyrimidinyl)methyl]-2-methyl-, chloride, monohydrochloride ; 5-[(2-methyl-2H-pyridin-1-yl)methyl]-2-propyl-pyrimidin-4-amine ; 5-[(6-methylpyridin-1-yl)methyl]-2-propyl-pyrimidin-4-amine chloride hydrochloride .?Amprolium hydrochloride(CAS NO.137-88-2) is used for treatment of anti-coccidiosis.

4.3 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TJ7565000

CHEMICAL NAME :: 2-Picolinium, 1-((4-amino-2-propyl-5-pyrimidinyl)methyl)-, chloride, monohydrochloride

CAS REGISTRY NUMBER :: 137-88-2

LAST UPDATED :: 199410

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C14-H19-N4.Cl.Cl-H

MOLECULAR WEIGHT :: 315.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 10 mg/plate

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 77,21,1980

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. Other Information

6.0 Usage: A thiamine analogue; blocks thiamine uptake and prevents carbohydrate synthesis

6.1 BRN: 4118699

6.2 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.

6.3 Chemical Properties: Crystalline powder

6.4 Uses: Coccidiostatic;Thiamine transport inhibitor

6.5 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.

6.6 Uses: Thiamine analog coccidiostat.

6.7 Contact allergens: Amprolium is an antiprotozoal agent used for the prevention of coccidiosis in poultry.

6.8 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.

7. Computational chemical data

Molecular Weight: 315.24g/mol
Molecular Formula: C₁₄H₂₀Cl₂N₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 314.1065020
Monoisotopic Mass: 314.1065020
Complexity: 246
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 55.7
Heavy Atom Count: 20
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 3
CACTVS Substructure Key Fingerprint: AAADceBzgAAGAAAAAAAAAAAAAAAAAAAAAAAsWAAAAAAAAAAB4AAAHAAQAAAADAjBHwQ/sJdMEACgAzZnZACCgCkxAqAJ2CA4ZJiIKOLA2dGEJAhogALIyCcQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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