| Identification | Back Directory | [Name]
Chlormezanone | [CAS]
80-77-3 | [Synonyms]
Lobak
Rexan
Rilax
Muskel
Alinam
Bisina
Banabin
Mio-Sed
Rilasol
Tanafol
win4692
FENAROL
WIN 4692
Trancote
Rillasol
Supotran
Suprotan
Rilassol
Rilansyl
Rilaquil
Phenarol
Miorilax
Clorilax
Myolespen
Trancopal
Transanate
Clormetazon
Chlomedinon
Chlormezanon
CHLORMEZANONE
Chlormethazone
Clormetazanone
Banabin-Sintyal
Banabin-syntyal
banabil-sintyal
Chlormethazanone
Dichloromezanone
Muskel-Trancopal
muskel-trancophl
Dichloromethazanone
ChlorMezanone (Trancopal)
2-(4-Chlorophenyl)-3-methyl-4-thiazanone 1,1-dioxide
2-(4-Chlorophenyl)-3-methyl-4-metathiazanone-1,1-dioxide
2-(4-chlorophenyl)-3-methyl-4-methathiazanone-1,1-dioxide
2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one
2-(4-chlorophenyl)-1,1-diketo-3-methyl-1,3-thiazinan-4-one
2-(p-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one
2-(4-Chlorophenyl)-3-methyl-1,3-thiazinan-4-one 1,1-dioxide
2-(p-Chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide
2-(p-chlorophenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide
2-(p-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one1,1-dioxide
2-(p-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxide
4h-1,3-thiazin-4-one,2-(4-chlorophenyl)tetrahydro-3-methyl-1,1-dioxide
4h-1,3-thiazin-4-one,2-(p-chlorophenyl)tetrahydro-3-methyl-1,1-dioxide
1,1-dioxide-2-(4-chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one
2-(4-CHLOROPHENYL)TETRAHYDRO-3-METHYL-4H,1,3-THIAZIN-4-ONE 1,1-DIOXIDE
4h-1,3-thiazin-4-one,tetrahydro-2-(p-chlorophenyl)-3-methyl-,1,1-dioxide
4h-1,3-thiazin-4-one,2-(p-chlorophenyl)tetrahydro-3-methyl-,1,1,-dioxide
4H-1,3-Thiazin-4-one, 2-(4-chlorophenyl)tetrahydro-3-methyl-, 1,1-dioxide
4H-1,3-Thiazin-4-one, 2-(p-chlorophenyl)tetrahydro-3-methyl-, 1,1-dioxide
2-(para-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one,1,1-dioxide
4H-1,3-Thiazin-4-one, tetrahydro-2-(p-chlorophenyl)-3-methyl-, 1,1-dioxide
4h-1,3-thiazin-4-one, 2-(p-chlorophenyl)tetrahydro-3-methyl-, 1,1,-dioxide 2-(4-chlorophenyl)-3-methyl-4-metathiazanone-1,1-dioxide 2-(p-chlorophenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide 2-(p-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one 1,1-dioxide 2-(p-chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide 2-(para-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one, 1,1-dioxide 4h-1,3-thiazin-4-one, 2-(4-chlorophenyl)tetrahydro-3-methyl-1,1-dioxide | [EINECS(EC#)]
201-307-4 | [Molecular Formula]
C11H12ClNO3S | [MDL Number]
MFCD00143951 | [MOL File]
80-77-3.mol | [Molecular Weight]
273.74 |
| Chemical Properties | Back Directory | [Melting point ]
114 °C | [Boiling point ]
534.5±50.0 °C(Predicted) | [density ]
1.2205 (rough estimate) | [refractive index ]
1.6300 (estimate) | [storage temp. ]
Store at RT | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
-2.37±0.40(Predicted) | [color ]
White to Pale Yellow | [Merck ]
14,2106 | [NIST Chemistry Reference]
Chlormezanone(80-77-3) |
| Hazard Information | Back Directory | [Uses]
Skeletal muscle relaxant | [Definition]
ChEBI: A 1,3-thiazine that is 1,3-thiazinan-4-one S,S-dioxide in which a hydrogen at position 2 is substituted by a 4-chlorophenyl group and the hydrogen attached to the nitrogen is substituted by methyl. A non-benzodiazepine
muscle relaxant, it was used in the management of anxiety and in the treatment of muscle spasms until being discontinued worldwide by its manufacturer in 1996, due to rare but serious cutaneous reactions. | [Biological Activity]
Anxiolytic and skeletal muscle relaxant that acts at the benzodiazepine site of GABA A receptors. | [Originator]
Trancopal,Winthrop-Breon,US,1958 | [Manufacturing Process]
A solution of 4-chlorobenzaldehyde is reacted with beta-mercaptopropionic
acid and with methylamine. The mixture is refluxed in benzene and water is
removed from an overhead separator. The reaction mixture was cooled,
washed with dilute ammonium hydroxide and water, and the benzene was
removed by distillation in vacuo. The oily residue was taken up in ether from
which it crystallized. The precipitate was recrystallized twice from ether to
yield 2-(4-chlorophenyl)-3-methyl-4-metathiazanone.
A solution of 11.2 g of potassium permanganate in 100 ml of warm water was
added dropwise to a well stirred solution of 10 g of 2-(4-chlorophenyl)-3-
methyl-4-metathiazanone in 50 ml of glacial acetic acid. The temperature was
kept below 30°C with external cooling. An aqueous sodium bisulfite solution
was then added to remove the manganese dioxide. The thick whitish oil which
separated was taken up in chloroform and the extract was washed with water.
Removal of the chloroform by distillation in vacuo yielded an oily residue
which solidified. The solid was recrystallized from isopropyl alcohol to give 5 gof the product, 2-(4-chlorophenyl)-3-methyl-4-metathiazanone-1,1-dioxide,
MP 116.2° to 118.6°C (corr.). | [Brand name]
Trancopal (Sanofi
Aventis). | [Therapeutic Function]
Tranquilizer | [World Health Organization (WHO)]
Chlormezanone is a sedative with antianxiety properties and a
central skeletal muscle relaxant effect. It had already been falling into
obsolescence for several years. | [Synthesis]
Chlormezanone, 2-(p-chlorophenyl)-tetrahydro-3-methyl-4H-1,3-
tiazin-4-on-1,1-dioxide (5.2.8), is synthesized by joint condensation of mercaptopropionic
acid, methylamine, and 4-chlorobenzaldehyde, evidently through the intermediate stage of
formation of 4-chlorobenzylidenemethylamine, giving the aminothioacetal 2-
(p-chlorophenyl)-tetrahydro-3-methyl-4H-1,3-tiazin-4-one (5.2.7). Oxidation of the sulfur
atom using potassium permanganate gives chlormezanone (5.2.8) [62,63].
| [storage]
Room temperature |
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