Tizanidine hydrochloride

Tizanidine hydrochloride Basic information
Description References
Product Name:Tizanidine hydrochloride
Synonyms:5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2;1,3-benzothiadiazol-4-amine,5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-mono;5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazolehydrochloride;SIRDALUD;TERNELIN;TIZANIDINE HCL;TIZANIDINE HYDROCHLORIDE;ZANAFLEX
CAS:64461-82-1
MF:C9H9Cl2N5S
MW:290.17
EINECS:
Product Categories:Zanaflex, Sirdalud;Bases & Related Reagents;Muscle relaxant (skeletal);Heterocycles;Nucleotides;Sulfur & Selenium Compounds;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Adrenoceptor;64461-82-1
Mol File:64461-82-1.mol
Tizanidine hydrochloride Structure
Tizanidine hydrochloride Chemical Properties
Melting point 280 °C
Fp 9℃
storage temp. Inert atmosphere,Room Temperature
solubility H2O: ~29 mg/mL
form solid
color white
Merck 14,9485
CAS DataBase Reference64461-82-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 26-36-37/39
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 3
RTECS DK9910000
HS Code 2934990002
MSDS Information
ProviderLanguage
SigmaAldrich English
Tizanidine hydrochloride Usage And Synthesis
DescriptionAs an adrenergic agonist with muscle relaxant activity, tizanidine hydrochloride belongs to the hydrochloride salt form of tizanidine, which is commonly used in the treatment of spasticity, a condition where muscles in human body spasm, cramp, or become tight induced by a variety of medical problems such as multiple sclerosis, spinal cord injury, Lou Gehrig's disease, spastic diplegia, back pain or certain other injuries to the spine or central nervous system. Besides, as a sleep aid and an anticonvulsant, tizanidine hydrochloride has off-label usage for migraine headaches and is effective for some symptoms of fibromyalgia.
As a short-acting muscle relaxer, the antinociceptive effect of tizanidine hydrochloride functions by blocking excess nerve impulses (pain sensations) of the nerve cells that are sent to the brain and control muscle movement, ultimately resulting in muscle relaxation and spasticity alleviation.
Referenceshttps://en.wikipedia.org/wiki/Tizanidine
http://www.webmd.com/drugs/2/drug-1024/tizanidine-oral/details
http://bodyandhealth.canada.com/drug/getdrug/pal-tizanidine
https://pubchem.ncbi.nlm.nih.gov/compound/114869#section=Top
https://www.drugs.com/tizanidine.html



Chemical PropertiesOff-White to pale Yellow Solid
OriginatorNimzox,Rapross Pharmaceuticals Pvt. Ltd.,India
UsesAn α2-adrenergic agonist; centrally active myotonolytic. A muscle relaxant (skeletal).
UsesTizanidine (Zanaflex) is a drug that is used as a muscle relaxant. It is a centrally acting α-2 adrenergic agonist. It is used to treat the spasms, cramping, and tightness of muscles caused by medical problems such as multiple sclerosis, spastic diplegia,
UsesAnticoagulant
DefinitionChEBI: Tizanidine hydrochloride is a benzothiadiazole.
Manufacturing Process14 ml of benzoyl chloride are added to a solution of 11.5 g of ammonium thiocyanate in 150 ml of acetone in an ice bath and the mixture is then stirred for 10 min. This solution is heated to the boil at reflux together with 19 g of 4-amino-5-chloro-2,1,3-benzothiadiazole. The solution is cooled to room temperature and diluted with a 4-fold quantity of water. The precipitate is filtered off and rapidly brought to a boil together with 150 ml of a 2 N aqueous sodium hydroxide solution and kept at the boil for 5 min. The solution is cooled to room temperature, is acidified weakly with glacial acetic acid, the precipitate is filtered off, washed with ether and recrystallized from methanol. The N-(5-chloro-2,1,3-benzothiadiazol-4-yl)thiourea, obtained and this is boiled for 1 h together with 9 g of methyl iodide in 150 ml of methanol. After concentrating by evaporation, crude S-methyl-N-(5-chloro-2,1,3- benzothiadiazol-4-yl)isothiuronium iodide is obtained. 9.8 g of S-methyl-N-(5- chloro-2,1,3-benzothiadiazol-4-yl)isothiuronium iodide are heated to the boil at reflux for 1 h together with 50 ml of methanol and 1.8 ml of ethylene diamine. The solvent is then removed by evaporation and the moist residue is boiled at reflux for 1 h together with 20 ml of n-amyl alcohol. The mixture is subsequently shaken with 50 ml of chloroform and 150 ml of water until all the material is dissolved. 40 ml of a 2 N aqueous sodium hydroxide solution are added to the aqueous phase and extraction is effected with 200 ml of chloroform. The organic phase is dried and concentrated by evaporation. After recrystallizing the residue from methanol with the addition of some active charcoal, 4-(2-imidazolin-2-yl-amino)-5-chloro-2,1,3-benzothiadiazole, having a melting point of 221-223°C, is obtained. The 4-(2-imidazolin-2-yl-amino)-5-chloro-2,1,3-benzothiadiazole hydrochloride may be obtained by the teaction of 4-(2-imidazolin-2-yl-amino)-5-chloro- 2,1,3-benzothiadiazole with hydrochloric acid.
Brand nameTizanidine is INN and BAN.
Therapeutic FunctionMuscle relaxant, Spasmolytic
Biological Activityα 2 -adrenergic receptor agonist. Antinociceptive upon epidural administration in rats (IC 50 = 48 nM). Also binds to imidazoline receptor.
storageDesiccate at RT
Tizanidine hydrochloride Preparation Products And Raw materials
Raw materialsIodomethane-->Benzoyl chloride-->Sodium hydroxide-->Hydrochloric acid-->2,1,3-Benzothiadiazole-->Ammonium thiocyanate-->Ethylenediamine
Olopatadine HCl Fexofenadine hydrochloride 2-Mercapto-5-methyl-1,3,4-thiadiazole 2-Aminoethylammonium chloride Topotecan hydrochloride Methoxyammonium chloride Clonidine hydrochloride ETHANOLAMINE HYDROCHLORIDE DIETHANOLAMINE HYDROCHLORIDE Difluorochloromethane Bis(2-ethylhexyl)amine Tizanidine hydrochloride Moxonidine hydrochloride DL-Octopamine hydrochloride Dihydromyrcenol Cyclohexylamine hydrochloride Cysteamine hydrochloride TIZANIDINE HYDROCHLORIDE

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