Tizanidine hydrochloride Chemical Properties

Melting point:

280 °C

Flash point:

9℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

H₂O: ~29 mg/mL

form 

solid

color 

white

Merck 

14,9485

CAS DataBase Reference

64461-82-1(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

• Language:English Provider:SigmaAldrich

Tizanidine hydrochloride Usage And Synthesis

Description

As 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.

References

https://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 Properties

Off-White to pale Yellow Solid

Originator

Nimzox,Rapross Pharmaceuticals Pvt. Ltd.,India

Uses

An α2-adrenergic agonist; centrally active myotonolytic. A muscle relaxant (skeletal).

Uses

Tizanidine (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,

Uses

Anticoagulant

Definition

ChEBI: Tizanidine hydrochloride is a benzothiadiazole.

Manufacturing Process

14 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 name

Tizanidine is INN and BAN.

Therapeutic Function

Muscle relaxant, Spasmolytic

Biological Activity

α 2 -adrenergic receptor agonist. Antinociceptive upon epidural administration in rats (IC 50 = 48 nM). Also binds to imidazoline receptor.

storage

Desiccate at RT

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