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| CAS No.: | 16595-80-5 |
|---|---|
| Name: | Levamisole hydrochloride |
| Molecular Structure: | |
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| Formula: | C11H12N2S.HCl |
| Molecular Weight: | 240.757 |
| Synonyms: | Imidazo[2,1-b]thiazole, 2,3,5, 6-tetrahydro-6-phenyl-, monohydrochloride, (-)-;Decaris;Prestwick_294;Tramisole;2,3,5,6-Tetrahydro-6-phenyl-imidazo[2,1-b]thiazole, (S)-;L(-)-Levamisole;Niratic-PurOn hydrochloride;(7S)-7-phenyl-4-thia-1,6-diazabicyclo[3.3.0]oct-5-ene hydrochloride;Tramisol;Ergamisol (TN);L-Tetramisole hydrochloride;Niratic hydrochloride;L-Narpenol;Imidazo[2, 1-b]thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, L-(-)-;Ergamisol; |
| EINECS: | 240-654-6 |
| Melting Point: | 266-267 ºC |
| Boiling Point: | 344.4 ºC at 760 mmHg |
| Flash Point: | 162.1 ºC |
| Solubility: | 210 g/L (20 ºC) in water |
| Appearance: | white to almost white crystalline powder |
| Hazard Symbols: |
 T, Xn
|
| Risk Codes: | 25-20/21/22 |
| Safety: | 36/37/39-45-28A-36 |
| Transport Information: | UN 2811 6.1/PG 3 |
| PSA: | 40.90000 |
| LogP: | 2.32160 |
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water | 94.2% |
Levamisole
levamisole hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: Levamisole With sodium metabisulfite; pyrographite In isopropyl alcohol for 0.5h; Stage #2: With hydrogenchloride pH=4 - 5; Time; | 92.1% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride In isopropyl alcohol; toluene Title compound not separated from byproducts; | A 16 g B n/a |
levamisole hydrochloride
Levamisole
| Conditions | Yield |
|---|---|
| With sodium hydroxide In diethyl ether; water Inert atmosphere; | 98% |
| With sodium hydroxide In water pH=12; | 98.32% |
| With sodium hydroxide In diethyl ether; water at 20℃; for 0.166667h; | 91% |
dodecacarbonyl-triangulo-triruthenium
levamisole hydrochloride
| Conditions | Yield |
|---|---|
| In tetrahydrofuran (under N2, Schlenk); mixt. of Ru3(CO)12 and ligand stirred in THF at reflux temp. for 40 min, cooled to room temp., left aside for 24 h; filtered, concd., hexane added, ppt. washed with hexane, dried in vacuo,recrystd. from CH2Cl2-hexane; elem. anal.; | A n/a B 9% |
Ru3(CH3CN)2(CO)10
levamisole hydrochloride
| Conditions | Yield |
|---|---|
| In dichloromethane (under N2, Schlenk); ligand added to CH2Cl2 soln. of Ru3(CO)10(MeCN)2, 2min; TLC on silica gel, heated to reflux for 1 h; |
Os3(CO)10(CH3CN)2
levamisole hydrochloride
| Conditions | Yield |
|---|---|
| In tetrahydrofuran (under N2, Schlenk); ligand added to THF soln. of Os3(CO)10(MeCN)2, stirred at reflux for 40 min; solvent removed under reduced pressure, residue dissolved in CH2Cl2, silica gel chromy. with hexane:CH2Cl2 4:1, and hexane:CH2Cl2 1:1; elem. anal.; |
| Conditions | Yield |
|---|---|
| Stage #1: trifluorobenzylideneacetone; levamisole hydrochloride With pivaloyl chloride; N-ethyl-N,N-diisopropylamine Stage #2: With 3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine In dichloromethane at 20℃; for 16h; | A n/a B n/a |
| Conditions | Yield |
|---|---|
| Stage #1: trifluorobenzylideneacetone; levamisole hydrochloride With pivaloyl chloride; N-ethyl-N,N-diisopropylamine Stage #2: With (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine In dichloromethane at -78℃; for 16h; enantioselective reaction; | A n/a B n/a C n/a |
levamisole hydrochloride
levamisole citrate
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: sodium hydroxide / water / pH 12 2: ethanol View Scheme |
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IUPAC Name: (6S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole hydrochloride
Molecular Formula: C11H12N2S.HCl
Molecular Weight: 240.75 g/mol
SMILES: c1([C@H]2CN3CCSC3=N2)ccccc1.Cl
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-;/m1./s1
EINECS: 240-654-6
Classification Code: Biological response modifier; Drug / Therapeutic Agent; Human Data; Immunomodulator; Mutation data; Reproductive Effect
Product Categories: API; Asymmetric Synthesis; Synthetic Organic Chemistry; Antibiotic Explorer; Veterinaries; Protein Phosphatase
Melting Point: 266-267 °C(lit.)
alpha: -128 °(c=5, H2O)
refractive index: -126 ° (C=1, H2O)
storage temperature: 0-6 °C
Water Solubility: 210 g/L (20 °C)
Flash Point: 162.1 °C
Enthalpy of Vaporization: 58.83 kJ/mol
Boiling Point: 344.4 °C at 760 mmHg
Vapour Pressure of Levamisole hydrochloride (CAS NO.16595-80-5): 6.61E-05 mmHg at 25 °C
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| frog | LD50 | parenteral | 363mg/kg (363mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 289, Pg. 278, 1987. | |
| mouse | LD50 | intramuscular | 121mg/kg (121mg/kg) | Fortschritte der Medizin. Vol. 94, Pg. 793, 1976. | |
| mouse | LD50 | intraperitoneal | 34mg/kg (34mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982. |
| mouse | LD50 | intravenous | 18mg/kg (18mg/kg) | BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982. |
| mouse | LD50 | oral | 223mg/kg (223mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982. |
| mouse | LD50 | subcutaneous | 52mg/kg (52mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982. |
| rat | LD50 | intraperitoneal | 42mg/kg (42mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982. |
| rat | LD50 | intravenous | 26mg/kg (26mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982. |
| rat | LD50 | oral | 180mg/kg (180mg/kg) | Archives of Toxicology. Vol. 54, Pg. 275, 1983. | |
| rat | LD50 | subcutaneous | 80mg/kg (80mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982. |
| women | TDLo | oral | 180mg/kg/36D (180mg/kg) | BLOOD: THROMBOCYTOPENIA | British Medical Journal. Vol. 2, Pg. 555, 1977. |
Poison by ingestion, intraperitoneal, subcutaneous, intravenous, and intramuscular routes. An experimental teratogen. Human systemic effects by ingestion: thrombocytopenia. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, SOx, and HCl.
Hazard Codes: 
T,
Xn
Risk Statements: 25-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R25 :Toxic if swallowed.
Safety Statements: 36/37/39-45-28A-36
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36:Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: NJ5960000
HazardClass: 6.1(b)
PackingGroup of Levamisole hydrochloride (CAS NO.16595-80-5): III
Levamisole hydrochloride (CAS NO.16595-80-5), its Synonyms are (-)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole monohydrochloride ; Ascaridil ; Citarin L ; Decaris ; Ergamisol ' Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (S)- ; Levamisole HCl ; Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (-)- (8CI) . It is white to almost white crystalline powder.
