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14769-73-4

Basic Information
CAS No.: 14769-73-4
Name: Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-, (6S)-
Molecular Structure:
Molecular Structure of 14769-73-4 (Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-, (6S)-)
Formula: C11H12N2S
Molecular Weight: 204.29
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
Solubility:
Appearance: white to off-white crystalline powder
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 40.90000
LogP: 1.51960
Synthetic route
16595-80-5

levamisole hydrochloride

14769-73-4

Levamisole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium carbonate In isopropyl alcohol60%
With sodium carbonate In isopropyl alcohol
112790-85-9

(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine hydrochloride

14769-73-4

Levamisole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With thionyl chloride In dichloromethane
56613-81-1

(S)-2-Amino-1-phenyl-1-ethanol

14769-73-4

Levamisole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
848186-80-1

(S)-2-((tert-butyldimethylsilyl)oxy)-2-phenylethanamine

14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: K2CO3; 18-crown-6 / Heating
2: TBAF / tetrahydrofuran
3: aq. ethanol / Heating
4: SOCl2 / CH2Cl2
View Scheme
848186-81-2

N-(2-chloroethyl)-2-tert-butyldimethylsilyloxy-2-phenylethanamine

14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: TBAF / tetrahydrofuran
2: aq. ethanol / Heating
3: SOCl2 / CH2Cl2
View Scheme
62779-70-8

(1S)-1-phenylethylene-1,2-diamine

14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol; water
2: sodium carbonate / isopropyl alcohol
View Scheme
Multi-step reaction with 2 steps
1: water / ethanol
2: sodium carbonate / isopropyl alcohol
View Scheme

(S)-1-phenylethane-1,2-diamine dihydrochloride

14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide
2: ethanol; water
3: sodium carbonate / isopropyl alcohol
View Scheme
51608-60-7

N-(benzylidene)-p-methylbenzenesulfonamide

14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: C40H40N2O3; copper(II) acetate monohydrate / toluene / 36 h / 20 °C / Inert atmosphere; Molecular sieve
2: hydrogen; palladium on activated charcoal / methanol / 20 °C
3: magnesium / methanol / 0.83 h / Sonication
4: water; ethanol
View Scheme

(S)-4-methyl-N-(2-nitro-1-phenylethyl)benzenesulfonamide

14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen; palladium on activated charcoal / methanol / 20 °C
2: magnesium / methanol / 0.83 h / Sonication
3: water; ethanol
View Scheme
14769-73-4

Levamisole

16595-80-5

levamisole hydrochloride

Conditions
ConditionsYield
Stage #1: Levamisole With sodium metabisulfite; pyrographite In isopropyl alcohol for 0.5h;
Stage #2: With hydrogenchloride pH=4 - 5; Time;
92.1%
15663-27-1

cisplatin

14769-73-4

Levamisole

silver nitrate

Pt(2+)*2NH3*C11H12N2S*Cl(1-)*NO3(1-)=[Pt(NH3)2(C11H12N2S)Cl](NO3)

Conditions
ConditionsYield
In N,N-dimethyl-formamide stirring Pt-complex with 1 equiv. AgNO3 for 24 h in dark, filtration, addn. of 1 equiv. ligand, stirring for at least 3 h; solvent removal (reduced pressure), collection (filtration), washing (CH2Cl2), recrystn. (water); can be purified by reversed phase chromy. (C18stationary phase, water); elem. anal.; product is cis-isomer;79%
14769-73-4

Levamisole

silver nitrate

Pt(2+)*2NH3*C11H12N2S*Cl(1-)*NO3(1-)=[Pt(NH3)2(C11H12N2S)Cl](NO3)

Conditions
ConditionsYield
In N,N-dimethyl-formamide stirring Pt-complex with 1 equiv. AgNO3 for 24 h in dark, filtration, addn. of 1 equiv. ligand, stirring for at least 3 h; solvent removal (reduced pressure), collection (filtration), washing (CH2Cl2), recrystn. (water); can be purified by reversed phase chromy. (C18stationary phase, water); elem. anal.; product is trans-isomer;75%
15663-27-1

cisplatin

14769-73-4

Levamisole

Pt(2+)*NH2CH2CH2NH2*C11H12N2S*2Cl(1-)=[Pt(NH2CH2CH2NH2)(C11H12N2S)Cl]Cl

Conditions
ConditionsYield
With AgNO3 In N,N-dimethyl-formamide stirring Pt-complex with 1 equiv. AgNO3 for 24 h in dark, filtration, addn. of 1 equiv. ligand, stirring for at least 3 h; solvent removal (reduced pressure), collection (filtration), washing (CH2Cl2), recrystn. (0.5 M HCl, then water); can be purified by reversed phase chromy. (C18 stationary phase, water); elem. anal.;75%
14769-73-4

Levamisole

86-84-0

1-Naphthyl isocyanate

65172-60-3

(6S,11aΞ)-1,3-di-naphthalen-1-yl-6-phenyl-tetrahydro-thiazolo[2',3':2,3]imidazo[1,2-a][1,3,5]triazine-2,4-dione

Conditions
ConditionsYield
In acetone
147-73-9

meso-tartaric acid

14769-73-4

Levamisole

levamisole D-tartrate

Conditions
ConditionsYield
In ethanol
14769-73-4

Levamisole

77-92-9

citric acid

32339-82-5

levamisole citrate

Conditions
ConditionsYield
In ethanol
14769-73-4

Levamisole

50-81-7

ascorbic acid

1400988-13-7

levamisole L-ascorbate

Conditions
ConditionsYield
In ethanol
1135-24-6

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

14769-73-4

Levamisole

levamisole ferulate

Conditions
ConditionsYield
In ethanol
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    14769-73-4

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    BLOOM TECH Advanced API/Technology support Levamisole CAS 14769-73-4

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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.

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