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16595-80-5

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16595-80-5 Usage

Chemical Properties

White to light yellow crystalline powder, odorless, bitter taste. Melting point 227-229℃. Soluble in water, methanol, ethanol and glycerol, slightly soluble in chloroform and aether; insoluble in acetone. Stable under acidic conditions, but easy to decompose and fail under alkaline conditions.

Uses

Different sources of media describe the Uses of 16595-80-5 differently. You can refer to the following data:
1. Biological response modifier with anthelmintic activity. Anthelmintic (nematodes); immunomodulator.
2. Levamisole hydrochloride is an anthelmintic. The activity of levamisole is about twice as high as that of abscisicidal, and the toxicity and side effects are lower. Levamisole can cause muscle paralysis of roundworms and then excrete them in the feces. It is mainly used as an anti-worm and anti-hookworm.

Preparation

Levamisole hydrochloride was prepared from racemic tetraimidazole by splitting, alkali analysis and acidification into salt.Dibenzoyl-D-tartaric acid is boiled in water for 40min, hydrolyzed and neutralized with sodium hydroxide solution to pH 7.5, and then added to racemic tetraimidazole. The levamisole is precipitated by generating salt with bisbenzoyl-tartaric acid. After separation, add sodium hydroxide solution to PH=9 and decompose levamisole. Then dissolved in dilute hydrochloric acid solution, after decolorization by activated carbon, the filtrate was concentrated nearly dry, and crystallized by adding acetone and cooling to 0℃. Filtered and dried to obtain levamisole hydrochloride.

Brand name

Ergamisol (Janssen);Vermisol.

Therapeutic Function

Antiinflammatory

Biochem/physiol Actions

Shows both immunostimulant and immunosuppressant effects, depending on several controllable factors. Very effective in treatment of ascariasis (hookworm infestation). Useful in chemotherapy of colorectal cancers, possibly due to its stimulation of IL-1 production and direct activation of macrophages.

Pharmacokinetics

Levamisole Hydrochloride is the hydrochloride salt of the synthetic imidazothiazole derivative levamisole with anthelminthic and immunomodulating activities. In immunosuppressed states, levamisole may restore immune function by: 1) stimulating antibody formation, 2) stimulating T-cell activation and proliferation, 3) potentiating monocyte and macrophage phagocytosis and chemotaxis and 4) increasing neutrophil mobility, adherence, and chemotaxis.

Mode of action

Levamisole is a cholinergic receptor agonist and elicits spastic muscle paralysis due to prolonged activation of the excitatory nicotinic acetylcholine receptors (nAChR) on nematode body wall muscle.

Toxicity evaluation

Symptoms of levamisole toxicity mimic organophosphate toxicity (salivation, lacrimation, urination and defecation, hyperesthesia, seizures and irritability). There is no antidote for levamisole toxicity.The World Health Organization reviewed hematological studies in animals and humans and derived acceptable daily intake for levamisole as 0.006 mg/kg body weight. This suggests a person can ingest 0.36 mg of levamisole/day over a lifetime without any appreciable risk.levamisole

Check Digit Verification of cas no

The CAS Registry Mumber 16595-80-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,5,9 and 5 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 16595-80:
(7*1)+(6*6)+(5*5)+(4*9)+(3*5)+(2*8)+(1*0)=135
135 % 10 = 5
So 16595-80-5 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/t10-;/m1./s1

16595-80-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (T1215)  Levamisole Hydrochloride  >99.0%(T)

  • 16595-80-5

  • 10g

  • 550.00CNY

  • Detail
  • TCI America

  • (T1215)  Levamisole Hydrochloride  >99.0%(T)

  • 16595-80-5

  • 25g

  • 950.00CNY

  • Detail
  • TCI America

  • (L0231)  Levamisole Hydrochloride [for Biochemical Research]  >99.0%(T)

  • 16595-80-5

  • 1g

  • 285.00CNY

  • Detail
  • TCI America

  • (L0231)  Levamisole Hydrochloride [for Biochemical Research]  >99.0%(T)

  • 16595-80-5

  • 5g

  • 580.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000047)  Levamisolehydrochlorideforsystemsuitability  European Pharmacopoeia (EP) Reference Standard

  • 16595-80-5

  • Y0000047

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (L0380000)  Levamisolehydrochloride  European Pharmacopoeia (EP) Reference Standard

  • 16595-80-5

  • L0380000

  • 1,880.19CNY

  • Detail
  • USP

  • (1359302)  Levamisolehydrochloride  United States Pharmacopeia (USP) Reference Standard

  • 16595-80-5

  • 1359302-125MG

  • 3,436.29CNY

  • Detail
  • Sigma-Aldrich

  • (31742)  Levamisolhydrochloride  VETRANAL, analytical standard

  • 16595-80-5

  • 31742-250MG

  • 525.33CNY

  • Detail

16595-80-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Levamisole hydrochloride

1.2 Other means of identification

Product number -
Other names Levamisole Hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Veterinary Drug: ANTHELMINTHIC_AGENT
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:16595-80-5 SDS

16595-80-5Synthetic route

levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt)

levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt)

toluene
108-88-3

toluene

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Conditions
ConditionsYield
With sodium hydroxide In water94.2%
Levamisole
14769-73-4

Levamisole

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Conditions
ConditionsYield
Stage #1: Levamisole With sodium metabisulfite; pyrographite In isopropyl alcohol for 0.5h;
Stage #2: With hydrogenchloride pH=4 - 5; Time;
92.1%
Tetramisole
5036-02-2

Tetramisole

A

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

B

(+)-Tetramisole hydrochloride
16595-76-9

(+)-Tetramisole hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol; toluene Title compound not separated from byproducts;A 16 g
B n/a
levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether; water Inert atmosphere;98%
With sodium hydroxide In water pH=12;98.32%
With sodium hydroxide In diethyl ether; water at 20℃; for 0.166667h;91%
dodecacarbonyl-triangulo-triruthenium
15243-33-1

dodecacarbonyl-triangulo-triruthenium

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Conditions
ConditionsYield
In tetrahydrofuran (under N2, Schlenk); mixt. of Ru3(CO)12 and ligand stirred in THF at reflux temp. for 40 min, cooled to room temp., left aside for 24 h; filtered, concd., hexane added, ppt. washed with hexane, dried in vacuo,recrystd. from CH2Cl2-hexane; elem. anal.;A n/a
B 9%
Ru3(CH3CN)2(CO)10
103257-53-0

Ru3(CH3CN)2(CO)10

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Conditions
ConditionsYield
In dichloromethane (under N2, Schlenk); ligand added to CH2Cl2 soln. of Ru3(CO)10(MeCN)2, 2min; TLC on silica gel, heated to reflux for 1 h;
levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Os3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Os3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Os3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Os3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Conditions
ConditionsYield
In tetrahydrofuran (under N2, Schlenk); ligand added to THF soln. of Os3(CO)10(MeCN)2, stirred at reflux for 40 min; solvent removed under reduced pressure, residue dissolved in CH2Cl2, silica gel chromy. with hexane:CH2Cl2 4:1, and hexane:CH2Cl2 1:1; elem. anal.;
trifluorobenzylideneacetone

trifluorobenzylideneacetone

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

C18H13F3O2

C18H13F3O2

C18H13F3O2

C18H13F3O2

Conditions
ConditionsYield
Stage #1: trifluorobenzylideneacetone; levamisole hydrochloride With pivaloyl chloride; N-ethyl-N,N-diisopropylamine
Stage #2: With 3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine In dichloromethane at 20℃; for 16h;
A n/a
B n/a
trifluorobenzylideneacetone

trifluorobenzylideneacetone

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

C18H13F3O2

C18H13F3O2

C18H13F3O2

C18H13F3O2

C18H13F3O2

C18H13F3O2

Conditions
ConditionsYield
Stage #1: trifluorobenzylideneacetone; levamisole hydrochloride With pivaloyl chloride; N-ethyl-N,N-diisopropylamine
Stage #2: With (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine In dichloromethane at -78℃; for 16h; enantioselective reaction;
A n/a
B n/a
C n/a
levamisole hydrochloride
16595-80-5

levamisole hydrochloride

levamisole citrate
32339-82-5

levamisole citrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / pH 12
2: ethanol
View Scheme
levamisole hydrochloride
16595-80-5

levamisole hydrochloride

levamisole ferulate

levamisole ferulate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / pH 12
2: ethanol
View Scheme
levamisole hydrochloride
16595-80-5

levamisole hydrochloride

levamisole D-tartrate

levamisole D-tartrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / pH 12
2: ethanol
View Scheme
levamisole hydrochloride
16595-80-5

levamisole hydrochloride

levamisole L-ascorbate
1400988-13-7

levamisole L-ascorbate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / pH 12
2: ethanol
View Scheme

16595-80-5Relevant articles and documents

A method for preparing the levamisole hydrochloride

-

Paragraph 0021; 0022, (2017/03/08)

The invention discloses a preparation method for levamisole hydrochloride, with low energy consumption, no wastewater, stable quality and high yield. The preparation method takes use of L-tetramisole as a raw material and comprises the steps of dissolving L-tetramisole in isopropanol; adding an antioxidant; decoloring with activated carbon; filtering; introducing a hydrogen chloride gas under stirring; controlling a pH value at an end point to be 4-5; and separating after reaction is finished, thus obtaining a finished product of levamisole hydrochloride. According to the preparation method, a novel better solvent of isopropanol is used in a salifying step. Isopropanol has a boiling point higher than that of acetone, low volatility, small system loss, high recovery rate and low unit consumption, and saves cost. The preparation technology is in no need of steaming water, has small wastewater discharge, produces no wastewater and has low energy consumption. The preparation technology omits a high temperature steaming water process; a product does not cake, has no generation of yellow spot, guarantees the quality of prepared levamisole hydrochloride, and has high yield. By adding the antioxidant, the quality stability of the product is increased; and the product has good appearance.

Process for isolating levamisole from tetramisole

-

, (2008/06/13)

A process for isolating levamisole or a therapeutically acceptable acid addition salt thereof from tetramisole or an acid addition salt thereof by precipitating levamisole. L-N-[(4-methoxyphenyl)sulfonyl]-glutamic acid (salt) and converting the diastereomeric salt into levamisole or a suitable acid addition salt thereof.

A CONVENIENT METHOD FOR OPTICAL RESOLUTIONS VIA DIASTEREOISOMERIC SALT FORMATION

Acs, M.,Fogassy, E.,Faigl, F.

, p. 2465 - 2470 (2007/10/02)

With the advantage of the method using two immiscible solvents and half-equivalent amount of the resolving agent, higher optical purity can be obtained than in cases of any other resolution via diastereoisomeric salt formation, besides it is a faster procedure for resolution of a new racemate as well.

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