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| CAS No.: | 14769-73-4 |
|---|---|
| Name: | Levamisole |
| Article Data: | 15 |
| Molecular Structure: | |
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| Formula: | C11H12N2S |
| Molecular Weight: | 204.296 |
| Synonyms: | (-)-Tetramisole;(S)-(-)-Levamisole;L-Tetramisole;Lepuron;Levamisol;Levipor;Levomysol;(S)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole;Totalon;Vermisol 150;Wormicid;l-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole;Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-, (S)-;(-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2.1-b]thiazole;Levamisole; |
| EINECS: | 238-836-5 |
| Density: | 1.326 g/cm3 |
| Melting Point: | 230 - 233ºC |
| Boiling Point: | 344.382 °C at 760 mmHg |
| Flash Point: | 162.076 °C |
| Appearance: | white to off-white crystalline powder |
| PSA: | 40.90000 |
| LogP: | 1.51960 |
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- 16595-80-5
levamisole hydrochloride
- 14769-73-4
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% |
- 75-15-0
carbon disulfide
- 62779-70-8
(1S)-1-phenylethylene-1,2-diamine
- 106-93-4
ethylene dibromide
- 14769-73-4
Levamisole
| Conditions | Yield |
|---|---|
| Stage #1: carbon disulfide; (1S)-1-phenylethylene-1,2-diamine In ethanol; water Stage #2: ethylene dibromide With sodium carbonate In ethanol; water | 65% |
- 16595-77-0
(S)-4-Phenyl-4,5-dihydro-1H-imidazole-2-thiol
- 106-93-4
ethylene dibromide
- 14769-73-4
Levamisole
| Conditions | Yield |
|---|---|
| With sodium carbonate In isopropyl alcohol | 60% |
| With sodium carbonate In isopropyl alcohol |
- 112790-85-9
(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine hydrochloride
- 14769-73-4
Levamisole
| Conditions | Yield |
|---|---|
| With thionyl chloride; potassium carbonate 1.)CH2Cl2, RT, 2 h, 2.) ethanol, reflux, 1 h; Yield given. Multistep reaction; |
- 5036-02-2
Tetramisole
- 14769-73-4
Levamisole
- 5036-02-2
Tetramisole
A
- 14769-73-4
Levamisole
B
- 14769-74-5
R-(+)-6-phenyl-2,3,5,6-tetrahydro-imidazo<2,1b>thiazole
| Conditions | Yield |
|---|---|
| With pyrographite; O,O'-dibenzoyl-L-tartaric acid In carbon dioxide at 39℃; under 120010 Torr; Product distribution; Further Variations:; Reagents; | |
| With O,O'-dibenzoyl-L-tartaric acid In dichloromethane; water at 40℃; Sonication; Irradiation; Overall yield = 84 %; | A n/a B n/a |
- 112790-83-7
(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine
- 14769-73-4
Levamisole
| Conditions | Yield |
|---|---|
| With thionyl chloride In dichloromethane |
- 56613-81-1
(S)-2-Amino-1-phenyl-1-ethanol
- 14769-73-4
Levamisole
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: imidazole 2: K2CO3; 18-crown-6 / Heating 3: TBAF / tetrahydrofuran 4: aq. ethanol / Heating 5: SOCl2 / CH2Cl2 View Scheme |
- 121673-61-8
N-(2-chloroethylamino)-1-phenyl-1-ethanol
- 14769-73-4
Levamisole
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: aq. ethanol / Heating 2: SOCl2 / CH2Cl2 View Scheme |
- 186343-35-1
(S)-5-phenyl-1,3-oxazolidine-2-one
- 14769-73-4
Levamisole
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: 79 percent / aq. NaOH / ethanol / Heating 2: imidazole 3: K2CO3; 18-crown-6 / Heating 4: TBAF / tetrahydrofuran 5: aq. ethanol / Heating 6: SOCl2 / CH2Cl2 View Scheme |
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Specification
The Levamisole, with the CAS registry number 14769-73-4, is also known as (S)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole. Its EINECS number is 238-836-5. This chemical's molecular formula is C11H12N2S and molecular weight is 204.29. What's more, its systematic name is (6S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole. Its classification codes are: (1)Adjuvants, immunologic; (2)Anthelmintics; (3)Anti-Infective Agents; (4)Antinematodal agents; (5)Antiparasitic Agents; (6)Antirheumatic agents; (7)Drug / Therapeutic Agent; (8)Immunologic Factors; (9)Mutation data. This chemical is used as antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. It should be sealed and stored at the temperature of 0 - 6 °C.
Physical properties of Levamisole are: (1)ACD/LogP: 1.84; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.16; (4)ACD/LogD (pH 7.4): -0.06; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 2.40; (8)ACD/KOC (pH 7.4): 2.99; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 40.9 Å2; (13)Index of Refraction: 1.713; (14)Molar Refractivity: 60.411 cm3; (15)Molar Volume: 154.109 cm3; (16)Polarizability: 23.949×10-24cm3; (17)Surface Tension: 54.1 dyne/cm; (18)Density: 1.326 g/cm3; (19)Flash Point: 162.076 °C; (20)Enthalpy of Vaporization: 58.834 kJ/mol; (21)Boiling Point: 344.382 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: N\2=C1/SCCN1C[C@@H]/2c3ccccc3
(2)Std. InChI: InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
(3)Std. InChIKey: HLFSDGLLUJUHTE-SNVBAGLBSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 43mg/kg (43mg/kg) | Pharmaceutical Chemistry Journal Vol. 30, Pg. 448, 1996. | |
| mouse | LD50 | intravenous | 22mg/kg (22mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: EXCITEMENT BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979. |
| mouse | LD50 | oral | 210mg/kg (210mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979. |
| mouse | LD50 | subcutaneous | 84mg/kg (84mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: EXCITEMENT BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979. |
| rabbit | LD50 | intravenous | 15mg/kg (15mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979. |
| rabbit | LD50 | oral | 700mg/kg (700mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: EXCITEMENT | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979. |
| rat | LD50 | intravenous | 24mg/kg (24mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: EXCITEMENT | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979. |
| rat | LD50 | oral | 480mg/kg (480mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979. |
| rat | LD50 | subcutaneous | 120mg/kg (120mg/kg) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | MBI, Mediko Biologicheskaya Informatsiya. Medical-Biological Information. Vol. (6), Pg. 27, 1985. |