(S)-(-)-Levamisole

Modify Date: 2024-01-03 11:03:48

(S)-(-)-Levamisole Structure
(S)-(-)-Levamisole structure
 Common Name (S)-(-)-Levamisole
CAS Number 14769-73-4 Molecular Weight 204.291
Density 1.3±0.1 g/cm3 Boiling Point 344.4±45.0 °C at 760 mmHg
Molecular Formula C11H12N2S Melting Point 230 - 233ºC
MSDS N/A Flash Point 162.1±28.7 °C

 Use of (S)-(-)-Levamisole


(S)-(-)-Levamisole (Levamisole), an anthelmintic agent with immunomodulatory properties. (S)-(-)-Levamisole acts as a positive allosteric modulator (PAM) for the α3β2 (EC50=300 μM) and α3β4 (EC50=100 μM) subtype of nAChRs. Orally active[1][2].

 Names

Name levamisole
Synonym More Synonyms

 (S)-(-)-Levamisole Biological Activity

Description (S)-(-)-Levamisole (Levamisole), an anthelmintic agent with immunomodulatory properties. (S)-(-)-Levamisole acts as a positive allosteric modulator (PAM) for the α3β2 (EC50=300 μM) and α3β4 (EC50=100 μM) subtype of nAChRs. Orally active[1][2].
Related Catalog
In Vivo (S)-(-)-Levamisole (Levamisole) (50 μg/ml and 200 μg/ml; p.o.; 30 days) prevents weight gain in mice that were fed a high fat diet[2].
References

[1]. Lewis JA, et al. Levamisole: A Positive Allosteric Modulator for the α3β4 Nicotinic Acetylcholine Receptors Prevents Weight Gain in the CD-1 Mice on a High Fat Diet. Curr Pharm Des. 2017;23(12):1869-1872.

[2]. Mehta KP, et al. Immunoregulatory treatment for minimal change nephrotic syndrome. Arch Dis Child. 1986;61(2):153-158.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 344.4±45.0 °C at 760 mmHg
Melting Point 230 - 233ºC
Molecular Formula C11H12N2S
Molecular Weight 204.291
Flash Point 162.1±28.7 °C
Exact Mass 204.072113
PSA 40.90000
LogP 1.85
Vapour Pressure 0.0±0.8 mmHg at 25°C
Index of Refraction 1.713
Storage condition 0-6°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NJ5940000
CHEMICAL NAME :
Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (S)-
CAS REGISTRY NUMBER :
14769-73-4
LAST UPDATED :
199512
DATA ITEMS CITED :
13
MOLECULAR FORMULA :
C11-H12-N2-S
MOLECULAR WEIGHT :
204.31

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
480 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
120 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory stimulation
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
24 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
210 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
84 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
22 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
700 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
15 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TEST SYSTEM :
Human
DOSE/DURATION :
2142 ug/kg
REFERENCE :
PTBIAN Pathologie Biologie. (Expansion Scientifique Francaise, 15, rue St. Benoit, F-75278 Paris Cedex 06, France) V.17- 1969- Volume(issue)/page/year: 28,323,1980 *** REVIEWS *** TOXICOLOGY REVIEW PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 2,407,1979

 Safety Information

Hazard Codes Xi
RIDADR UN 2811
HS Code 2934999090

 Synthetic Route

 Customs

HS Code 2934100090
Summary 2934100090 other compounds containing an unfused thiazole ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

 Synonyms

MFCD00792481
6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole
Imidazo[2,1-b]thiazole, 2,3,5,6-tetrahydro-6-phenyl-
levomysol
L-teramisole
6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
lepuron
UNII:C8M7RFE4NO
(±)-Tetramisole
dl-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole
6-Phenyl-2,3,5,6-tetrahydroimidazo(2,1-b)thiazole
dl-Tetramisol
LEVAMISOLE BASE
EINECS 238-836-5
Tetramisole
2,3,5,6-Tetrahydro-6-phenyl-imidazo(2,1-b)thiazole
Levamisole
Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-
dl-2,3,5,6-tetrahydro-6-phenylimidazo(2,1-b)thiazole
(±)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole
(±)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole
Ketrax
dl-Tetramisole
Nilverm base
Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (±)-
tetramizole
l-tetramisole
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