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16595-80-5

Basic Information
CAS No.: 16595-80-5
Name: Levamisole hydrochloride
Article Data: 5
Cas Database
Molecular Structure:
Molecular Structure of 16595-80-5 (Levamisole hydrochloride)
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
Density: N/A
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: ToxicT,HarmfulXn
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
Synthetic route
levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt)

levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt)

108-88-3

toluene

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Conditions
ConditionsYield
With sodium hydroxide In water94.2%
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%
5036-02-2

Tetramisole

A

16595-80-5

levamisole hydrochloride

B

16595-76-9

(+)-Tetramisole hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol; toluene Title compound not separated from byproducts;A 16 g
B n/a
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%
15243-33-1

dodecacarbonyl-triangulo-triruthenium

16595-80-5

levamisole hydrochloride

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Conditions
ConditionsYield
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%
103257-53-0

Ru3(CH3CN)2(CO)10

16595-80-5

levamisole hydrochloride

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Ru3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Conditions
ConditionsYield
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;
16595-80-5

levamisole hydrochloride

Os3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Os3(μ-Cl)(μ-1-ethyelenethiolate-3-H-4-(S)-phenylimidazolin-2-ylidene)(CO)9

Conditions
ConditionsYield
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.;

trifluorobenzylideneacetone

16595-80-5

levamisole hydrochloride

C18H13F3O2

C18H13F3O2

Conditions
ConditionsYield
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

trifluorobenzylideneacetone

16595-80-5

levamisole hydrochloride

C18H13F3O2

C18H13F3O2

C18H13F3O2

Conditions
ConditionsYield
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
16595-80-5

levamisole hydrochloride

32339-82-5

levamisole citrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / pH 12
2: ethanol
View Scheme
Raw Materials
5036-02-2
Downstream Products
14769-73-4
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    Product name Levamisole hydrochloride CAS NO. 16595-80-5 Appearance White crystalline powder EINECS 240-654-6 MW

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Chemistry


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

Toxicity Data With Reference

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.

Safety Profile

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: ToxicT,HarmfulXn
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

Specification

 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.