Product Name

  • Name

    Levamisole

  • EINECS 238-836-5
  • CAS No. 14769-73-4
  • Article Data15
  • CAS DataBase
  • Density 1.326 g/cm3
  • Solubility
  • Melting Point 230 - 233ºC
  • Formula C11H12N2S
  • Boiling Point 344.382 °C at 760 mmHg
  • Molecular Weight 204.296
  • Flash Point 162.076 °C
  • Transport Information
  • Appearance white to off-white crystalline powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 14769-73-4 (Levamisole)
  • Hazard Symbols
  • 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;
  • PSA 40.90000
  • LogP 1.51960

Synthetic route

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Levamisole
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%
carbon disulfide
75-15-0

carbon disulfide

(1S)-1-phenylethylene-1,2-diamine
62779-70-8

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

ethylene dibromide
106-93-4

ethylene dibromide

Levamisole
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%
...Expand
(S)-4-Phenyl-4,5-dihydro-1H-imidazole-2-thiol
16595-77-0

(S)-4-Phenyl-4,5-dihydro-1H-imidazole-2-thiol

ethylene dibromide
106-93-4

ethylene dibromide

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
With sodium carbonate In isopropyl alcohol60%
With sodium carbonate In isopropyl alcohol
(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine hydrochloride
112790-85-9

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

Levamisole
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;
Tetramisole
5036-02-2

Tetramisole

Levamisole
14769-73-4

Levamisole

Tetramisole
5036-02-2

Tetramisole

A

Levamisole
14769-73-4

Levamisole

B

R-(+)-6-phenyl-2,3,5,6-tetrahydro-imidazo<2,1b>thiazole
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
(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine
112790-83-7

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

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
With thionyl chloride In dichloromethane
(S)-2-Amino-1-phenyl-1-ethanol
56613-81-1

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

Levamisole
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
N-(2-chloroethylamino)-1-phenyl-1-ethanol
121673-61-8

N-(2-chloroethylamino)-1-phenyl-1-ethanol

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. ethanol / Heating
2: SOCl2 / CH2Cl2
View Scheme
(S)-5-phenyl-1,3-oxazolidine-2-one
186343-35-1

(S)-5-phenyl-1,3-oxazolidine-2-one

Levamisole
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
(S)-2-((tert-butyldimethylsilyl)oxy)-2-phenylethanamine
848186-80-1

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

Levamisole
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
N-(2-chloroethyl)-2-tert-butyldimethylsilyloxy-2-phenylethanamine
848186-81-2

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

Levamisole
14769-73-4

Levamisole

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

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

Levamisole
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

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

Levamisole
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
N-(benzylidene)-p-methylbenzenesulfonamide
51608-60-7

N-(benzylidene)-p-methylbenzenesulfonamide

Levamisole
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

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

Levamisole
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
Levamisole
14769-73-4

Levamisole

levamisole hydrochloride
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%
cisplatin
15663-27-1

cisplatin

Levamisole
14769-73-4

Levamisole

silver nitrate

silver nitrate

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

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%
...Expand
transplatin
26035-31-4, 14913-33-8, 15663-27-1

transplatin

Levamisole
14769-73-4

Levamisole

silver nitrate

silver nitrate

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

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%
...Expand
cisplatin
15663-27-1

cisplatin

Levamisole
14769-73-4

Levamisole

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

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%
Levamisole
14769-73-4

Levamisole

1-Naphthyl isocyanate
86-84-0

1-Naphthyl isocyanate

(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
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
meso-tartaric acid
147-73-9

meso-tartaric acid

Levamisole
14769-73-4

Levamisole

levamisole D-tartrate

levamisole D-tartrate

Conditions
ConditionsYield
In ethanol
Levamisole
14769-73-4

Levamisole

citric acid
77-92-9

citric acid

levamisole citrate
32339-82-5

levamisole citrate

Conditions
ConditionsYield
In ethanol
Levamisole
14769-73-4

Levamisole

ascorbic acid
50-81-7

ascorbic acid

levamisole L-ascorbate
1400988-13-7

levamisole L-ascorbate

Conditions
ConditionsYield
In ethanol
3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

Levamisole
14769-73-4

Levamisole

levamisole ferulate

levamisole ferulate

Conditions
ConditionsYield
In ethanol

Levamisole 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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