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16595-80-5, Levamisole (hydrochloride)

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Use of Levamisole (hydrochloride)
Levamisole Hcl is an anthelmintic and immunomodulator belonging to a class of synthetic imidazothiazole derivatives.IC50 value: Target: Levamisole suppresses the production of white blood cells, resulting in neutropenia and agranulocytosis. With the increasing use of levamisole as an adulterant, a number of these complications have been reported among cocaine users [1] [2]. Levamisole reversibly and noncompetitively inhibits most isoforms of alkaline phosphatase (e.g., human liver, bone, kidney, and spleen) except the intestinal and placental isoform [3]. It is thus used as an inhibitor along with substrate to reduce background alkaline phosphatase activity in biomedical assays involving detection signal amplification by intestinal alkaline phosphatase, for example in in situ hybridization or Western blot protocols. It is used to immobilize the nematode C. elegans on glass slides for imaging.

Names

Name Levamisole hydrochloride
Synonym More Synonyms

 Levamisole (hydrochloride) Biological Activity

Description Levamisole Hcl is an anthelmintic and immunomodulator belonging to a class of synthetic imidazothiazole derivatives.IC50 value: Target: Levamisole suppresses the production of white blood cells, resulting in neutropenia and agranulocytosis. With the increasing use of levamisole as an adulterant, a number of these complications have been reported among cocaine users [1] [2]. Levamisole reversibly and noncompetitively inhibits most isoforms of alkaline phosphatase (e.g., human liver, bone, kidney, and spleen) except the intestinal and placental isoform [3]. It is thus used as an inhibitor along with substrate to reduce background alkaline phosphatase activity in biomedical assays involving detection signal amplification by intestinal alkaline phosphatase, for example in in situ hybridization or Western blot protocols. It is used to immobilize the nematode C. elegans on glass slides for imaging.
Related Catalog
References [1]. Centers for Disease Control and Prevention (CDC). Agranulocytosis associated with cocaine use – four States, March 2008-November 2009.MMWR Morb Mortal Wkly Rep. 2009 Dec 18;58(49):1381-5.[2]. Zhu NY, et al. Agranulocytosis after consumption of cocaine adulterated with levamisole. Ann Intern Med. 2009 Feb 17;150(4):287-9.

[3]. Van Belle H. Alkaline phosphatase. I. Kinetics and inhibition by levamisole of purified isoenzymes from humans. Clin Chem. 1976 Jul;22(7):972-6.

 Chemical & Physical Properties

Boiling Point 344.4ºC at 760 mmHg
Melting Point 226-231ºC
Molecular Formula C11H13ClN2S
Molecular Weight 240.752
Flash Point 162.1ºC
Exact Mass 240.048798
PSA 40.90000
LogP 2.32160

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NJ5960000
CHEMICAL NAME :
Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, L-(-)-
CAS REGISTRY NUMBER :
16595-80-5
LAST UPDATED :
199710
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C11-H12-N2-S.Cl-H
MOLECULAR WEIGHT :
240.77

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human – woman
DOSE/DURATION :
180 mg/kg/36D
TOXIC EFFECTS :
Blood – thrombocytopenia
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
180 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
42 mg/kg
TOXIC EFFECTS :
Behavioral – tremor Behavioral – convulsions or effect on seizure threshold Lungs, Thorax, or Respiration – other changes
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Behavioral – tremor Behavioral – convulsions or effect on seizure threshold Lungs, Thorax, or Respiration – other changes
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
26 mg/kg
TOXIC EFFECTS :
Behavioral – tremor Behavioral – convulsions or effect on seizure threshold Lungs, Thorax, or Respiration – other changes
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
223 mg/kg
TOXIC EFFECTS :
Behavioral – tremor Behavioral – convulsions or effect on seizure threshold Lungs, Thorax, or Respiration – other changes
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
34 mg/kg
TOXIC EFFECTS :
Behavioral – tremor Behavioral – convulsions or effect on seizure threshold Lungs, Thorax, or Respiration – other changes
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
52 mg/kg
TOXIC EFFECTS :
Behavioral – tremor Behavioral – convulsions or effect on seizure threshold Lungs, Thorax, or Respiration – other changes
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
18 mg/kg
TOXIC EFFECTS :
Behavioral – tremor Behavioral – convulsions or effect on seizure threshold Lungs, Thorax, or Respiration – other changes
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
121 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Amphibian – frog
DOSE/DURATION :
363 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
10800 mg/kg/13W-I
TOXIC EFFECTS :
Endocrine – changes in spleen weight Blood – normocytic anemia Nutritional and Gross Metabolic – weight loss or decreased weight gain
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal – dog
DOSE/DURATION :
10800 mg/kg/26W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder – changes in tubules (including acute renal failure, acute tubular necrosis) Blood – changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical – Enzyme inhibition, induction, or change in blood or tissue levels – transaminases
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal – dog
DOSE/DURATION :
1800 mg/kg/13W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration – dyspnea Blood – normocytic anemia Biochemical – Enzyme inhibition, induction, or change in blood or tissue levels – phosphatases
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
330 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive – Effects on Embryo or Fetus – fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
480 mg/kg
SEX/DURATION :
female 19-22 day(s) after conception lactating female 4 day(s) post-birth
TOXIC EFFECTS :
Reproductive – Effects on Newborn – viability index (e.g., # alive at day 4 per # born alive)
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
750 mg/kg
SEX/DURATION :
female 19-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive – Effects on Newborn – growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2125 mg/kg
SEX/DURATION :
female 19-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive – Effects on Newborn – weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

MUTATION DATA

TEST SYSTEM :
Rodent – mouse
DOSE/DURATION :
10 mg/kg
REFERENCE :
CCROBU Cancer Chemotherapy Reports, Part 1. (Washington, DC) V.52(6)-59, 1968-75. For publisher information, see CTRRDO. Volume(issue)/page/year: 59,531,1975

Synonyms

(-)-Tetramisole hydrochloride
Solaskil
Imidazo[2,1-b]thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (6S)-, hydrochloride (1:1)
Spartakon
Levamisol hydrochloride
(-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole hydrochloride
(6S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazolhydrochlorid
(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride
Ascaridil
Levasole
Meglum
Levadin
MFCD00005536
(S)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole Monohydrochloride
L[-]-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole
(-)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole monohydrochloride
Decaris
L-(-)-2,3,5,6-Tetrahydro-6-phenyl-imidazo(2,1-b)thiazole hydrochloride
(-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole monohydrochloride
Nilverm
Ripercol
L(−)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole hydrochloride
Levamisole HCl
Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, L-(-)-
L-(-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole Monohydrochloride
EINECS 240-654-6
Tramisol
(6S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole hydrochloride (1:1)
L-Tetramisole hydrochloride
Levamisole hydrochloride
Imidazo[2,1-b]thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, L-(-)-
Levacide
Ergamisol
Nemicide
(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole hydrochloride
Levamisole (hydrochloride)

 

 

 

 


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