ChemicalBook > CAS DataBase List > Levamisole hydrochloride

Levamisole hydrochloride

Product Name
Levamisole hydrochloride
CAS No.
16595-80-5
Chemical Name
Levamisole hydrochloride
Synonyms
LEVAMISOLE HCL;TETRAMISOLE HCL;LEVAMISOL HYDROCHLORIDE;citarinl;ERGAMISOL;decaris;Levadin;Dekaris;r-12,564;solaskil
CBNumber
CB7853188
Molecular Formula
C11H13ClN2S
Formula Weight
240.75
MOL File
16595-80-5.mol
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Levamisole hydrochloride Property

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
biological source
synthetic (organic)
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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
L-025
Product name
(−)-Levamisole hydrochloride solution
Purity
1.0?mg/mL in methanol (as free base), ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$146
Updated
2024/03/01
Sigma-Aldrich
Product number
31742
Product name
Levamisol hydrochloride
Purity
VETRANAL , analytical standard
Packaging
250mg
Price
$87.3
Updated
2024/03/01
Sigma-Aldrich
Product number
1359302
Product name
Levamisole hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
125mg
Price
$358
Updated
2024/03/01
TCI Chemical
Product number
L0231
Product name
Levamisole Hydrochloride [for Biochemical Research]
Purity
>99.0%(T)
Packaging
1g
Price
$37
Updated
2024/03/01
TCI Chemical
Product number
L0231
Product name
Levamisole Hydrochloride [for Biochemical Research]
Purity
>99.0%(T)
Packaging
5g
Price
$72
Updated
2024/03/01
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Levamisole hydrochloride Chemical Properties,Usage,Production

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.

Side effects

Levamisole hydrochloride oral side effects are dose-related, mild and transient. The most common side effects are fever and gastrointestinal symptoms. Other possible side effects include: rash, changes in taste and smell, granulocytopenia and/or leukopenia, arthralgia/myalgia, convulsions, failure, peripheral neuropathy, tachycardia, thrombocytopenia, vasculitis, and vertigo.

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

Levamisole hydrochloride Preparation Products And Raw materials

Raw materials

(1S)-(+)-Camphor-10-sulphonic acid Dibenzoyl-D-tartaric acid Levamisole Water DL-Tetramisole BP(V)98 Benzene Dilute hydrochloric acid L(+)-Tartaric acid

Preparation Products

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View Lastest Price from Levamisole hydrochloride manufacturers

Guangdong Junhua Chemical Co., Ltd
Product
Levamisole hydrochloride 16595-80-5
Price
US $220.00-79.00/kg
Min. Order
1kg
Purity
99％pure
Supply Ability
1000kg
Release date
2024-12-25
Guangdong Junhua Chemical Co., Ltd
Product
Levamisole hydrochloride 16595-80-5
Price
US $220.00-79.00/kg
Min. Order
1kg
Purity
99％pure
Supply Ability
1000kg
Release date
2024-12-25
Dorne Chemical Technology co. LTD
Product
Levamisole hydrochloride 16595-80-5
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
1000g
Release date
2024-03-26

16595-80-5, Levamisole hydrochlorideRelated Search:

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