(S)-(-)-Levamisole

Names

[ Name ]:
(S)-(-)-Levamisole

[Synonym ]:
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

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]:

Research Areas >> Infection

Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR

Signaling Pathways >> Neuronal Signaling >> nAChR

Research Areas >> Inflammation/Immunology

[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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%