886-74-8 Usage
Description
Chlorphenesin Carbamate, also known as Maolate, is a pharmaceutical compound derived from the lead compound mephenesin. It is a p-chloro substituted and 1-carbamate derivative that exhibits increased activity and lipophilicity due to p-chlorination and carbamylation of the primary hydroxyl group. This modification results in a centrally acting skeletal muscle relaxant with a biological half-life of 3.5 hours in humans.
Uses
Used in Pharmaceutical Industry:
Chlorphenesin Carbamate is used as a centrally acting muscle relaxant for the symptomatic treatment of painful muscle spasm. The carbamylation of the primary hydroxyl group increases its activity, while p-chlorination enhances lipophilicity and prevents para-position hydroxylation, leading to a more effective muscle relaxant.
Used in Muscle Relaxant Applications:
Chlorphenesin Carbamate is employed as a muscle relaxant to alleviate muscle pain and spasms. Its central action on the skeletal muscles helps in reducing discomfort and improving mobility in individuals suffering from muscle-related issues.
Originator
Maolate ,Upjohn ,US ,1967
Manufacturing Process
1.0 mol of 3-p-chlorophenoxy-1,2-propanediol (chlorphenesin) is suspended in
1,000 ml of benzene in a 5-liter flask equipped with a dropping funnel,
thermometer and stirrer. 1.0 mol of phosgene in 500 ml of cold, dry benzene
is then added dropwise over a period of 45 minutes, the resulting mixture
being maintained at 30°C until all solid material is dissolved. 1.0 mol of
triethylamine is added dropwise and the resulting reaction mixture stirred for
45 minutes at 30°C following the addition. The reaction mixture is then cooled
to 5°C and extracted repeatedly with 600 ml portions of cold water to remove
the triethylamine hydrochloride.
The benzene fraction, containing the intermediate 3-p-chlorophenoxy-3-
hydroxypropyl chlorocarbonate, is added to 600 ml of cold concentrated
ammonium hydroxide and the resulting reaction mixture agitated vigorously at
5°C for 7 hours. The crude 3-p-chlorophenoxy-2-hydroxypropylcarbamate
solid is then filtered off, dissolved in hot benzene, dried to remove all traces of
water, and permitted to crystallize out. Several recrystallirations from solvent
mixtures of benzene and toluene, with small amounts of acetone, produced a
crystalline white solid in about 65% yield. The product is 3-p-chlorophenoxy-
2-hydroxypropyl carbamate, melting at 89° to 91°C. The chlorphenesin
starting material is made by reacting p-chlorophenol with glyceryl
monochlorohydrin as noted in US Patent 3,214,336.
Therapeutic Function
Muscle relaxant
Check Digit Verification of cas no
The CAS Registry Mumber 886-74-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,8 and 6 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 886-74:
(5*8)+(4*8)+(3*6)+(2*7)+(1*4)=108
108 % 10 = 8
So 886-74-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H12ClNO4/c11-7-1-3-9(4-2-7)15-5-8(13)6-16-10(12)14/h1-4,8,13H,5-6H2,(H2,12,14)
