Tizanidine hydrochloride

Tizanidine hydrochloride is an α2-adrenergic receptor agonist and inhibits neurotransmitter release from CNS noradrenergic neurons.Target: α2-adrenergic receptorTizanidine is a drug that is used as a muscle relaxant. It is a centrally acting α2 adrenergic agonist. It is used to treat the spasms, cramping, and tightness of muscles caused by medical problems such as multiple sclerosis, ALS, spastic diplegia, back pain, or certain other injuries to the spine or central nervous system. It is

Tizanidine hydrochloride is a benzothiadiazole.|Tizanidine Hydrochloride is the hydrochloride salt form of tizanidine, an imidazoline derivative structurally similar to clonidine and an adrenergic agonist with muscle relaxant property. Tizanidine stimulates alpha-2 adrenergic receptors in the central nervous system, thereby inhibiting presynaptic release of norepinephrine and increasing the inhibitory effect on alpha motor neurons and motor reflexes. Tizanidine exerts some activity at the postsynaptic excitatory amino acid receptors and imidazoline receptors which may contribute to the overall reduction in facilitation of spinal motor neurons. Overall, tizanidine hydrochloride causes muscle relaxation, reduces spasticity and antinociceptive effects.

18.6 g of 4-amino-5-chloro-2, 1, 3-benzothiadiazole and 15.4 g of 1-acetylimidazolin-2-one were weighed and added to 120 ml of phosphorus oxychloride to raise the temperature to 60 to 65. °C reaction for 36 hours. The solvent was evaporated under reduced pressure, 160 ml of methanol was added to the obtained oil, and the mixture was heated to reflux for 4 hours. After cooling to room temperature, the reaction solution was poured into 160 ml of ice water, and the pH of the aqueous solution of sodium hydroxide was adjusted to 9-10. Filter and dry. 17.8 g of powdered solid tizanidine was obtained in a yield of 70percent.The resulting tizanidine was added to 100 ml of a saturated ethanolic hydrogen chloride solution and stirred at room temperature for 2 hours. After filtration, the filter cake was washed with anhydrous ethanol and dried. The filter cake was added to 200 ml of 95percent ethanol, refluxed until completely dissolved, naturally cooled, crystallized, filtered, and the filter cake was washed with anhydrous ethanol and dried to obtain solid tizanidine hydrochloride 17 g in a yield of 83.5percent with a purity of 99.22percent.Tizanidine 45g was added to 180mL of acetone, Heated to reflux, 21.3 g of acetic acid was added, Solution clarification, Slow down to a solid precipitation, Keep heating for 2 hours, And then cool down to 0 ° C below, Crystallization for 3 hours, filter, Dried to give 51.4 g of crude tizanidine acetate as an off-white solid, the yield was 92.4percentDirectly for the next step. Tizanidine acetate crude 50g, Was added to 200 mL of acetone, Heated to reflux, 24 g of acetic acid was added, Solution clarification, 10 mL of hydrochloric acid was added, Slow down to a solid precipitation, Insulation reaction 2 hours, And then cool to 0-10 ° C, Crystallization for 3 hours, filter, Dried to give 39.7 g of tizanidine hydrochloride as a white solid, The yield was 87.8percentPurity of 99.9percent.Weigh 18.6 g of 4-amino-5-chloro-2, 1, 3-benzothiadiazole and 15.4 g 1-Acetyl imidazolin-2-one, added to 120 mL of phosphorus oxychloride, Warm up to 60-65°C for 36 hours.The solvent is distilled off under reduced pressureAdd 160 mL of methanol to the resulting oil.The reaction was heated at reflux for 4 hours.Cold to room temperature, The reaction solution was poured into 160 mL of ice water.The aqueous sodium hydroxide solution adjusts the pH to 9-10.filter, dry.Trizanidol powdered solid 18g, yield 71percent.The resulting tizanidine is added to 100 mL of saturated hydrogen chloride ethanol solution, Stir for 1 hour at room temperature. Filtration, no filter cakeAfter washing with ethanol and drying, ethanol was recrystallized to obtain solid tizanidine hydrochloride 17.5g, the yield was 85.0percent, and the purity was 99.25percent.

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

Molecular Weight:290.17
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:288.9955719
Monoisotopic Mass:288.9955719
Topological Polar Surface Area:90.4
Heavy Atom Count:17
Complexity:300
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes