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ChemicalBook >> CAS DataBase List >>Levamisole hydrochloride

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
Molecular Weight:
240.75
MDL Number:
MFCD00012675
MOL File:
16595-80-5.mol
MSDS File:
SDS
Last updated:2024-12-18 14:08:57

Levamisole hydrochloride 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)
FDA UNII DL9055K809
NCI Drug Dictionary Ergamisol
EPA Substance Registry System Levamisole hydrochloride (16595-80-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P301+P310+P330
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
NFPA 704
3
0 0

Levamisole hydrochloride price More Price(35)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich L-025 (?)-Levamisole hydrochloride solution 1.0?mg/mL in methanol (as free base), ampule of 1?mL, certified reference material, Cerilliant? 16595-80-5 1mL $146 2024-03-01 Buy
Sigma-Aldrich 31742 Levamisol hydrochloride VETRANAL , analytical standard 16595-80-5 250mg $87.3 2024-03-01 Buy
Sigma-Aldrich 1359302 Levamisole hydrochloride United States Pharmacopeia (USP) Reference Standard 16595-80-5 125mg $358 2024-03-01 Buy
TCI Chemical L0231 Levamisole Hydrochloride [for Biochemical Research] >99.0%(T) 16595-80-5 1g $37 2024-03-01 Buy
TCI Chemical L0231 Levamisole Hydrochloride [for Biochemical Research] >99.0%(T) 16595-80-5 5g $72 2024-03-01 Buy
Product number Packaging Price Buy
L-025 1mL $146 Buy
31742 250mg $87.3 Buy
1359302 125mg $358 Buy
L0231 1g $37 Buy
L0231 5g $72 Buy

Levamisole hydrochloride Chemical Properties,Uses,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.

Definition

ChEBI: Levamisole hydrochloride is an organic molecular entity.

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.

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

14769-73-4
16595-80-5
Synthesis of Levamisole hydrochloride from Levamisole
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View Lastest Price from Levamisole hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Levamisole hydrochloride pictures 2024-12-22 Levamisole hydrochloride
16595-80-5
 US $220.00-79.00 / kg 1kg 99％pure 1000kg Guangdong Junhua Chemical Co., Ltd
Levamisole hydrochloride pictures 2024-12-22 Levamisole hydrochloride
16595-80-5
 US $220.00-79.00 / kg 1kg 99％pure 1000kg Guangdong Junhua Chemical Co., Ltd
Levamisole hydrochloride pictures 2024-12-22 Levamisole hydrochloride
16595-80-5
 US $0.00 / G 1G 99% 20 CONTIDE BIOTECH CO.,LTD
1-b)thiazole,2,3,5,6-tetrahydro-6-phenyl-,monohydrochloride,(s)-imidazo( 1-b)thiazole,2,3,5,6-tetrahydro-6-phenyl-,monohydrochloride,l-(-)-imidazo( 1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-,monohydrochloride,(S)-Imidazo[2 decaris Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-,monohydrochloride,(S)- kw-2-le-t L-2,3,5,6-Tetrahydro-6-phenylimidazo-[2,1-6]-thiazole levomysolhydrochloride l-tetramisolehydrochloride niratichydrochloride niratic-puronhydrochloride nsc-177023 r-12,564 ripercol-l L-(-)-2,3,5,6-TETRAHYDRO-6-PHENYLIMIDAZO (2,1B)THIAZOLE HCL L(-)-2,3,5,6-TETRAHYDRO-6-PHENYLIMIDAZO[2,1-B]THIAZOLE HYDROCHLORIDE L[-]-2,3,5,6-TETRA-HYDRO-6-PHENYLIMIDAZO[2,1-B]THIAZOLE HYDROCHLORIDE (+/-)-2,3,5,6-TETRAHYDRO-6-PHENYLIMIDAZO[2,1-B]THIAZOLE HYDROCHLORIDE [+/-]-2,3,5,6-TETRAHYDRO-6-PHENYLIMIDAZO[2,1-B]THIAZOLE HYDROCHLORIDE hydrochloric acid levamisole Levamisole HCL BP2000/EP97 Levamisole HCL BP2000/EP97/CP2000 LEVAMISOL HYDROCHLORIDE VETRANAL, 250 LEVAMISOLE HYDROCHLORIDE, 99+% LevamisoleHclBp2000 Ergamisol hydrochloride Imidazo2,1-bthiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (6S)- (-)-tetramizole hydrochloride (-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole hydrochloride Levamisole hydrochloride LevaMisole Hydrochloride(ErgaMisol) LevaMisole Hydrochloride COS (-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole Hydrochloride (-)-Tetramisole Hydrochloride LevaMisole Hydrochloride  Century-Ace ErgaMisole L-Narpenol LevaMisol HCl USP LEVAMISOLEHYDROCHLORIDE,USP (6S)-2,3,5,6-tetrahydro-6-phenyl-imidazo[2,1-b]thiazole,hydrochloride (1:1) Levamisole hydrochloride for system suitability L(?)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole (?)-Levamisole hydrochloride solution )-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole hydrochloride Levamisole hydrochloride solaskil stimamizolhydrochloride tramisole worm-chek (S)-(-)-6-PHENYL-2,3,5,6-TETRAHYDROIMIDAZO[2,1-B]THIAZOLE HYDROCHLORIDE TETRAMISOL HYDROCHLORIDE TRAMISOL Levamisole Hc1 (-)-Tetramisole hydrochloride, (-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole hydrochloride, S(-)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride, L(-)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole (-)-Tetramisole hydrochloride, Levamisole hydrochloride, L(-)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole hydrochloride, (S)-(-)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride Levamisole hydrochloride, L(-)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole hydrochloride, (S)-(-)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride Ascaridil Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, L-(-) Levacide