10-[2-(dimethylamino)propyl]-N,N-dimethyl-10H-phenothiazine-2-sulphonamide monomethanesulphonate manufacturers
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| | 10-[2-(dimethylamino)propyl]-N,N-dimethyl-10H-phenothiazine-2-sulphonamide monomethanesulphonate Basic information |
| | 10-[2-(dimethylamino)propyl]-N,N-dimethyl-10H-phenothiazine-2-sulphonamide monomethanesulphonate Chemical Properties |
| Toxicity | LD50 oral in rat: 1320mg/kg |
| | 10-[2-(dimethylamino)propyl]-N,N-dimethyl-10H-phenothiazine-2-sulphonamide monomethanesulphonate Usage And Synthesis |
| Originator | Migristene,Rhone Poulenc,France,1965 | | Uses | Dimethothiazine mesylate is an orally active tricyclic anti-histamine, anti-5-HT agent with a high activity against decerebrate rigidity, a little sedative activity and little soporific action. Dimethothiazine mesylate can reduce or abolish the effects of both static and dynamic fusimotor activity on the muscle spindle in decerebrate cat. Dimethothiazine mesylate can be used to research hemicrania and spasticity[1][2][3]. | | Definition | ChEBI: Dimethothiazine mesylate is a member of phenothiazines, a sulfonamide and a methanesulfonate salt. | | Manufacturing Process | A solution of 3-dimethylsulfamoylphenthiazine (10 grams) in xylene (100 cc)
is heated under reflux for 3 hours with sodium amide (1.5 grams). A solution
of 1-dimethylamino-2-chloropropane (4.4 grams) in anhydrous xylene (30 cc)
is then added and heating under reflux continued for 4 hours. After cooling
the suspension obtained is agitated with water (50 cc) and ether (30 cc). The
aqueous layer is separated and the basic products are extracted from the
organic phase with 10% hydrochloric acid. The xylene layer is discarded and,
after the combined acid solutions have been made alkaline with sodium
carbonate, the base is extracted with chloroform. The chloroform solutions are
then washed with water and dried over anhydrous potassium carbonate. After
evaporation of the solvent under reduced pressure there is obtained a crude
resinous base (9.7 grams).
On the addition of ethereal hydrogen chloride to a solution of the base in
isopropanol and recrystallization from anhydrous ethanol of the salt formed,
there is obtained 3-dimethylsulfamoyl-10-(2-dimethylaminopropyl)
phenthiazine hydrochloride (2.1 grams), MP 214°C with decomposition. After
dissolving the product in anhydrous ethanol and adding methanesulfonic acid
there is obtained fonazine mesylate. | | References | [1] Nattero G, et al. Use of dimethothiazine in the prevention of hemicrania. Minerva Med. 1977 Mar 17;68(13):839-45. PMID:321991
[2] Maxwell DR, Rhodes KF. The effects of dimethothiazine on muscle spindle activity in the decerebrate cat. Br J Pharmacol. 1970 Jul;39(3):520-32. DOI:10.1111/j.1476-5381.1970.tb10360.x
[3] Griffiths MI, et al. The use of dimethothiazine in the treatment of childhood cerebral palsy. Dev Med Child Neurol. 1973 Feb;15(1):25-32. DOI:10.1111/j.1469-8749.1973.tb04862.x |
| | 10-[2-(dimethylamino)propyl]-N,N-dimethyl-10H-phenothiazine-2-sulphonamide monomethanesulphonate Preparation Products And Raw materials |
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