Levamisole hydrochloride Chemical Properties

Melting point:

266-267 °C(lit.)

alpha 

-128 º (c=5, H2O)

refractive index 

-126 ° (C=1, H2O)

Flash point:

9℃

storage temp. 

2-8°C

solubility 

Freely soluble in water, soluble in ethanol (96 per cent), slightly soluble in methylene chloride.

form 

Crystalline Powder

color 

White to almost white

Water Solubility 

210 g/L (20 ºC)

Merck 

14,5459

BRN 

4358988

BCS Class

3/1

Stability:

Hygroscopic

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-;/s3

InChIKey

LAZPBGZRMVRFKY-HNCPQSOCSA-N

SMILES

[C@H]1(N=C2SCCN2C1)C1=CC=CC=C1.Cl |&1:0,r|

LogP

1.845 (est)

CAS DataBase Reference

16595-80-5(CAS DataBase Reference)

EPA Substance Registry System

Levamisole hydrochloride (16595-80-5)

Safety Information

Hazard Codes 

T,Xn,F

Risk Statements 

25-20/21/22-39/23/24/25-23/24/25-11

Safety Statements 

36/37/39-45-28A-36-36/37-16

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

NJ5960000

F 

10

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29349990

MSDS

• Language:English Provider:(-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Levamisole hydrochloride Usage And Synthesis

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.

Originator

Solaskil,Specia,France,1971

Uses

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.

Uses

Biological response modifier with anthelmintic activity. Anthelmintic (nematodes); immunomodulator.

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.

Definition

ChEBI: Levamisole hydrochloride is an organic molecular entity.

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.

Pharmacology

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.

Pharmacokinetics

Levamisole is rapidly absorbed from all routes of administration, with peak blood levels occurring within an hour followed by rapid metabolism and depletion principally via urinary excretion, with an elimination half-life of approximately 4 h.

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

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