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5086-74-8

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5086-74-8 Usage

Chemical Properties

Tetraimidazole hydrochloride is a white to pale cream crystalline powder, bitter and astringent, easily soluble in water , Methanol, slightly soluble in ethanol, insoluble in acetone. acid solutions are stable; however, hydrolysis occurs under alkaline conditions. The rate of hydrolysis increases with pH and temperature. It is used as levamisole intermediate, anthelmintic drug.

Uses

Tetramisole hydrochloride is an inhibitor of alkaline phosphatases, is a high purity antiparasitic. It is suitable for inhibition of various alkaline phosphatase (i.e., liver, kidney, placenta, bone and tumor)(Intestinal alkaline phosphatases are only slightly inhibited.). Tetramisole has biological response modifier with anthelmintic activity. Anthelmintic (nematodes); immunomodulator.

Definition

ChEBI: Tetramisole hydrochloride is an organic molecular entity. It is a broad-spectrum veterinary anthelmintic with high efficiency and low toxicity.

Application

Tetramisole is an alkaline phosphatase inhibitor. It is a racemic mixture of (+) and (-) isomers. The (-) isomer (levamisole) accounts for most of the biological activity of tetramisole.Tetramisole has been used to inhibit alkaline phosphatase in the effective range of 0.4 – 2 mM. Inhibition of intestinal alkaline phosphate requires higher concentrations. In addition to its use in enzyme and protein phosphorylation studies, tetramisole has been used to study membrane, tissue and animal systems.Tetramisole is an anthelminthic agent used in veterinary applications to treat helminth or worm infections.

in vitro

Tetramisole hydrochloride at 67.5 mg/kg is 88.8% effective against immature and 99.7% effective against adult Libyostrongylus douglassi of the ostrich. A dose of up to 408 mg/kg tetramisole hydrochloride had no adverse effects on young birds but at 529 mg/kg was lethal to both chicks and adult ostriches. The efficacy of pyrantel tartrate was erratic. At 50 - 60 mg/kg it was 72.3% effective against immatures and 50.2% effective against adult worms. At 100 mg/kg it fell to 43.6% against immature, but rose to 77.3% against adult worms. Pyrantel tartrate at 100 mg/kg caused the death .of three out of four chicks. The macroscopic lesions of the disease ""vrotmaag"" caused by L. douglassi are descriptionbed as well as some of the other pathological lesions observed at autopsy.

Mode of action

Tetramisole HCl inhibits parasitic worm growth by acting as an agonist to nicotinic acetylcholine receptors leading to paralysis. The mechanism of action for anticancer activity is unknown.

Check Digit Verification of cas no

The CAS Registry Mumber 5086-74-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,0,8 and 6 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5086-74:
(6*5)+(5*0)+(4*8)+(3*6)+(2*7)+(1*4)=98
98 % 10 = 8
So 5086-74-8 is a valid CAS Registry Number.
InChI:InChI=1/C11H12N2S.ClH/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10;/h1-5,10H,6-8H2;1H

5086-74-8 Well-known Company Product Price

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  • Sigma-Aldrich

  • (31743)  Tetramisolehydrochloride  VETRANAL, analytical standard

  • 5086-74-8

  • 31743-250MG

  • 360.36CNY

  • Detail

5086-74-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetramisole hydrochloride

1.2 Other means of identification

Product number -
Other names Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-, hydrochloride (1:1)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5086-74-8 SDS

5086-74-8Synthetic route

phosphorous pentasulfide

phosphorous pentasulfide

pyrographite
7440-44-0

pyrographite

1-(2-acetoxy-ethyl)-4-phenyl-imidazolidin-2-one
65329-73-9

1-(2-acetoxy-ethyl)-4-phenyl-imidazolidin-2-one

tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In ethanol; chloroform; toluene
With hydrogenchloride; sodium hydroxide In ethanol; chloroform; toluene
phosphorous pentasulfide

phosphorous pentasulfide

1-(2-methoxy-ethyl)-4-phenyl-imidazolidin-2-one
65329-69-3

1-(2-methoxy-ethyl)-4-phenyl-imidazolidin-2-one

tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In ethanol; chloroform; toluene
phosphorous pentasulfide

phosphorous pentasulfide

1-(2-hydroxy-ethyl)-4-phenyl-imidazolidin-2-one
65329-72-8

1-(2-hydroxy-ethyl)-4-phenyl-imidazolidin-2-one

tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In ethanol; chloroform; toluene
With hydrogenchloride; sodium hydroxide In ethanol; chloroform; toluene
1-(2-methoxy-ethyl)-4-phenyl-imidazolidine-2-thione
65329-70-6

1-(2-methoxy-ethyl)-4-phenyl-imidazolidine-2-thione

tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; acetone
With hydrogenchloride In ethanol; acetone
1-(2-methoxy-ethyl)-4-phenyl-imidazolidin-2-one
65329-69-3

1-(2-methoxy-ethyl)-4-phenyl-imidazolidin-2-one

tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; diphosphorus pentasulfide; sodium hydroxide In ethanol; chloroform; toluene
Multi-step reaction with 2 steps
1: hydrogenchloride; sodium hydroxide / chloroform; acetone; toluene
2: hydrogenchloride / ethanol; acetone
View Scheme
1-(2-hydroxy-ethyl)-4-phenyl-imidazolidine-2-thione
69510-65-2

1-(2-hydroxy-ethyl)-4-phenyl-imidazolidine-2-thione

tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

Conditions
ConditionsYield
In hydrogenchloride; isopropyl alcohol
α-bromoacetophenone
70-11-1

α-bromoacetophenone

tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid / methanol; dichloromethane; chloroform; water
2: palladium / ethanol; hydrogen
3: hydrogenchloride; diphosphorus pentasulfide; sodium hydroxide / ethanol; chloroform; toluene
View Scheme
Multi-step reaction with 4 steps
1: acetic acid / methanol; dichloromethane; chloroform; water
2: palladium / ethanol; hydrogen
3: hydrogenchloride; sodium hydroxide / chloroform; acetone; toluene
4: hydrogenchloride / ethanol; acetone
View Scheme
1-(2-methoxy-ethyl)-4-phenyl-1,3-dihydro-imidazol-2-one
65346-98-7

1-(2-methoxy-ethyl)-4-phenyl-1,3-dihydro-imidazol-2-one

tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium / ethanol; hydrogen
2: hydrogenchloride; diphosphorus pentasulfide; sodium hydroxide / ethanol; chloroform; toluene
View Scheme
Multi-step reaction with 3 steps
1: palladium / ethanol; hydrogen
2: hydrogenchloride; sodium hydroxide / chloroform; acetone; toluene
3: hydrogenchloride / ethanol; acetone
View Scheme
tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

Tetramisole
5036-02-2

Tetramisole

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether; water at 20℃; for 0.5h; Inert atmosphere;95%
dodecacarbonyl-triangulo-triruthenium
15243-33-1

dodecacarbonyl-triangulo-triruthenium

tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

[Ru3(μ-Cl)(μ-.eta(2)-levamisole-C,S)(CO)9]

[Ru3(μ-Cl)(μ-.eta(2)-levamisole-C,S)(CO)9]

Conditions
ConditionsYield
In tetrahydrofuran all manipulations under N2; mixt. of Ru and org. compds. in THF stirred and refluxed for 40 min; cooled to room temp., filtered, filtrate concd., pptd. with hexane, elem. anal.;93%
tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

3-styryl-thiazolidin-2-ylideneamine
20406-02-4, 37430-07-2

3-styryl-thiazolidin-2-ylideneamine

Conditions
ConditionsYield
In methanol
tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

(+)-tetramisole*CSA

(+)-tetramisole*CSA

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; diethyl ether / 0.5 h / 20 °C / Inert atmosphere
2: sodium hydroxide / chloroform / 12 h / -20 °C / Sealed tube
View Scheme
tetramisole hydrochloride
5086-74-8

tetramisole hydrochloride

R-(+)-6-phenyl-2,3,5,6-tetrahydro-imidazo<2,1b>thiazole
14769-74-5

R-(+)-6-phenyl-2,3,5,6-tetrahydro-imidazo<2,1b>thiazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water; diethyl ether / 0.5 h / 20 °C / Inert atmosphere
2: sodium hydroxide / chloroform / 12 h / -20 °C / Sealed tube
3: sodium hydroxide / diethyl ether; water / 0.5 h / 20 °C / Inert atmosphere
View Scheme

5086-74-8Relevant articles and documents

Method for the treatment of plants with agrochemical tablet compositions

-

, (2008/06/13)

Novel method for applying agrochemicals to plants, which method consists in attaching to the surface of the plants tablets comprising at least one agrochemically active compound and at least one adjuvant, which is solid, liquid of pasty at room temperature, and optionally, one or more excipients optionally in admixture with one or more other additives and/or water.

Derivatives of R,S-[X2-(2-hydroxyethylamino)-1-phenyl]-ethylamine, and process

-

, (2008/06/13)

An R,S-[2-(2-hydroxyethylamino)-1-phenyl]-ethylamine of the formula III STR1 wherein R represents hydrogen, allyl, propargyl or benzyl. These compounds provide valuable intermediates for the synthesis of Tetramisole.

Optically active 1-oxyethyl-4-phenyl-2-imidazolidones

-

, (2008/06/13)

A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives, and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of the anthelmintic levamisole, (-)-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives through conventional resolution procedures. The new process also permits the direct manufacture of optically active 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidone and their 3-acylated derivatives, optically active 1-(2-alkoxyethyl)-4-phenylimidazolidine-2-thiones, and levamisole, the levorotatory isomer of tetramisole, using catalytic amounts of a chiral reducing agent, with the elimination of conventional resolution procedures.

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