CAS No.16595-80-5,Levamisole hydrochloride Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	16595-80-5
Name:	Levamisole hydrochloride
Article Data:	5
Cas Database

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

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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

Conditions	Yield
With sodium hydroxide In water	94.2%

: 14769-73-4
Levamisole

: 16595-80-5
levamisole hydrochloride

Conditions

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%

: 5036-02-2
Tetramisole

A: 16595-80-5
levamisole hydrochloride

B: 16595-76-9
(+)-Tetramisole hydrochloride

Conditions

Conditions	Yield
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

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%

: 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

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%

...Expand

: 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

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;

...Expand

: 61817-93-4, 146143-79-5, 871132-66-0
Os3(CO)10(CH3CN)2

: 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

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.;

...Expand

: trifluorobenzylideneacetone

: 16595-80-5
levamisole hydrochloride

: C18H13F3O2

: C18H13F3O2

Conditions

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

...Expand

: trifluorobenzylideneacetone

: 16595-80-5
levamisole hydrochloride

: C18H13F3O2

: C18H13F3O2

: C18H13F3O2

Conditions

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

...Expand

: 16595-80-5
levamisole hydrochloride

: 32339-82-5
levamisole citrate

Conditions

Conditions	Yield
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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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 NO_x, SO_x, and HCl.
Hazard Codes: Toxic T, Harmful 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

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.

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