ChemicalBook CAS DataBase List 7456-24-8

7456-24-8

Name	Dimetotiazine
CAS	7456-24-8
EINECS(EC#)	231-229-6
Molecular Formula	C19H25N3O2S2
MDL Number	MFCD00868048
Molecular Weight	391.557
MOL File	7456-24-8.mol

Synonyms

8599RP Fonazine Bayer 1483 Dimethodin Brn 0941549 Dimetotiazine Dimetiotazine Dimethiotazine Dimetothiazine Dimethothiazine Dimetotiazine USP/EP/BP 13115-40-7 (Monomesylate) 3-Dimethylsulfonamido 10-(2-dimethylaminopropyl)phenothiazine Dimethylsulfamido-3-(dimethylamino-2-propyl)-10-phenothiazine 10-[2-(Dimethylamino)propyl]-N,N-dimethylphenothiazine-2-sulfonamide N,N-Dimethyl-10-[2-(dimethylamino)propyl]-10H-phenothiazine-2-sulfonamide 10H-Phenothiazine-2-sulfonamide, 10-[2-(dimethylamino)propyl]-N,N-dimethyl- Phenothiazine-2-sulfonamide, 10-[2-(dimethylamino)propyl]-N,N-dimethyl- (6CI, 7CI, 8CI) 10-(2-dimethylaminopropyl)-N,N-dimethyl-phenothiazine-2-sulfonamide: m ethanesulfonic acid

Chemical Properties

Boiling point	533.7±60.0 °C(Predicted)
density	1.1822 (rough estimate)
refractive index	1.6560 (estimate)
pka	8.91±0.50(Predicted)

Hazard Information

Originator

Migristene,Rhone Poulenc,France,1965

Uses

Serotonin inhibitor.

Definition

ChEBI: Dimetotiazine is a member of phenothiazines.

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.

in vivo

Dimethothiazine (0.5-16 mg/kg; i.v.; single dosage) reduces decerebrate rigidity in cats^[2].

Animal Model:	Cats (decerebrate model; the carotid arteries were clamped and the mid-brain sectioned approximately between the colliculae)^[2]
Dosage:	0.5, 1, 2, 4, 8 and 16 mg/kg
Administration:	i.v.; single dosage
Result:	Reduced the discharge frequency of primary and secondary endings at 1-4 mg/kg. Reduced the sensitivity of the muscle spindle to stretch in preparations with intact ventral roots. Reduced the activity of the dynamic fusimotor fibres.

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