80-77-3 Usage
Originator
Trancopal,Winthrop-Breon,US,1958
Uses
Different sources of media describe the Uses of 80-77-3 differently. You can refer to the following data:
1. Chlormezanone improves the emotional state of the patient, relieving moderate anxiety
and stress. However, it has a number of side effects, and because it does not have any
advantage over other anxiolytics, it is rarely used in practice.
2. The use of chlormezanone is associated with large increases in the risk of Stevens-Johnson syndrome or toxic epidermal necrolysis.
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.
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.
Biological Activity
Anxiolytic and skeletal muscle relaxant that acts at the benzodiazepine site of GABA A receptors.
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].
Check Digit Verification of cas no
The CAS Registry Mumber 80-77-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 80-77:
(4*8)+(3*0)+(2*7)+(1*7)=53
53 % 10 = 3
So 80-77-3 is a valid CAS Registry Number.
InChI:InChI=1/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3
80-77-3Relevant articles and documents
Tranquillizer chlormezanone synthesis method
-
Paragraph 0019-0030, (2018/07/30)
The invention discloses a tranquillizer chlormezanone synthesis method, which comprises: adding 2-(3-chloro-1,2-dihydroxyphenyl)-3-methyl-1,3-hydrothiazin-4-one and a chloromethyl methyl ether solution to a reaction container, carrying out controlled stirring, controlling the temperature of the solution, adding a 2-methyl-2,4-pentanediol solution, adding potassium ruthenate in batches, and continuously carrying out the reaction; and cooling the solution, adding a potassium carbonate solution in batches, layering the solution, taking out the oil layer, adding a benzenesulfonic acid solution, adjusting the pH value, extracting multiple times with a hexafluorobenzene solution, extracting multiple times with a dimethyl phosphate solution, washing with a 1,2-dibromobenzene solution, re-crystallizing in a polypropylene glycol solution, and dehydrating with a dehydrating agent to obtain the finished product chlormezanone.
Water dispersion containing ultrafine particles of organic compounds
-
, (2008/06/13)
A water-dispersible condensate of water-insoluble ultrafine particles of medicine or hormones having a particle size of at largest 4 μm prepared by the steps of heating the medicine or hormone in a vacuum vessel at a temperature of 30° C. higher than the boiling point and at a pressure between 0.01 Torr and 10 Torr to evaporate the medicine or hormone and condensing the medicine or hormone on a recovery plate to obtain the condensate.
