Propanediol carbamates

Methyl-2-propyl-l, 3-propanediol carbamate isopropylcarbamate N-Iso-propylmeprobamate. Carisoma (Pharmax, U.K.) Rella (Schering-Plough)... 

Alkylene diols are also referred to as propanediol carbamates have been used as tranquilizer. Two mportant members of this classification, namely meprobamate and tybamate have been discussed in the Chapter-8 on Muscle Relaxants in this book. 

As both (+) and (-)-isomers produced tranqullization in rats, the action is not attributed to p-adrenergic blockade. Although pyridarone (26) was the most potent member of a series studied for neurodepressant activity in animals, anti-anxiety action could not be confirmed in a clinical study. Fenpentadlol (27) displayed anti-anxiety and stimulant properties in animals. Meprobamate-like activity was noted in pharmacological studies of Insem-5 (28). The pharmacology of propanediol carbamates was reviewed recently. ... 

A solution of 32 g (030 mol) phosgene in 200 ml benzene is added dropwise at 30°C to a stirred soiution of 53.5 g (032 mol) 3-o-toloxy-13-Pfopanediol in 400 ml benzene. The mixture is stirred for an hour after the addition is completed, and a solution of 39 g of dl-methylaniline in 100 ml benzene is then added, and stirring continued for a half-hour. Ice water (about one-third volume) is then added, and the benzene layer formed is separated and stirred with 500 ml concentrated ammonia at 5°Cfor six hours. The precipitated solid (weighing about 55 g) is recovered and recrystallized from water. The product thus obtained in a yield of about 53 g is 3-(o-toloxy)-2-hydroxypropyl carbamate it is a crystalline solid melting at about 93°C, and having a lower water-solubility and higher oil-solubility than 3-o-toloxy-13-propanediol. 

Diethylmethyl propylmalonate is reacted with LiAIH4, then H2SO4 to give 2-methyl-2-propyl-1,3-propanediol. That is reacted with phosgene in toluene to give the chlorocar-bonate which is in turn reacted with butylamine to give N-butyl-2-methyl-2-propyl-3-hy-droxy-propyl carbamate. 

Methocarbamol Methocarbamol, 3-(2-methoxyphenoxy)-l,2-propanediol-l carbamate (15.3.13), is synthesized by successive reaction with phosgene and then ammonia into 3-(2-methoxyphenoxy)propanediol-1,2 [34,35]. 

In the same way 2-47 and 3-47a dialkylamino alcohols were methylated, silylated and stannylatcd via chiral x-lithiated carbamate sparteine complexes (>95- >98% ee), as well as 1,3-propanediol and 1,4-butanediol (95 >99.5% ee)45. 

Chemical Name 3-(4-Chlorophenoxy)-l,2-propanediol-l-carbamate Common Name 3-p-Chlorophenoxy-2-hydroxypropyl carbamate Structural Formula ... 

PROPANEDIOL DICARBAMATE 2-METHYL-2-PROPYLTRIMETHYLENE CARBAMATE METRACTYL... 

METHYLPROPYL METHACRYLATE see IIYOOO METHYL-N-PROPYLNITROSAMINE see MNAOOO METHYLPROPYLNITROSOAMINE see MNAOOO 2-(l -METHYLPROPYL)PHEN X METHYLCARBAMATE see MOVOOO 2-METHYL-2-N-PROPYL-L3-PROPANEDIOL DICARBAMATE see MQU750 2-METHYLPROPYLPROPANOIC ACID-2-METHYLPROPYL ESTER (9CI) see IIWOOO 2-METHYLPROPYL PROPIONATE see PM "250 2-METHYL-2-PROPYLTRIMETHYLENE CARBAMATE see MQU750... 

Chlorphenesin Carbamate. Chlorphenesin carbamate. 3-(/>-chlorophenoxy)-l.2-propanediol l-carbamate (Mao-... 

Methocarbamol, described in the early literature as AHR-85, is known as 3-(2-methoxyphenoxy)-1,2-propanediol 1-carbamate 3-(o-methoxyphenoxy)-2-hydroxypropyl 1-carbamate 2-hydroxy-3-(o-methoxyphenoxy)propyl 1-carbamate, or guaifenesin carbamate. The term methocarbamol refers to the racemate unless otherwise specified. 

The name used by Chemical Abstracts and U.S.PJKin for meprobamate is 2-methyl-2-propyl-1,3 propanediol dicarbamate. It can also be called 2,2-di(carbamoyloxymethyl) pentane or 2-methyl-2-propyltrimethylene carbamate. The empirical formula is C Hng Oh with a molecular weight of 218.2. ... 

Berger, F. M. The anticonvulsant activity of carbamate esters of certain 2,2-disubstituted-l,3-propanediols. J. Pharmacol. Exp. Ther. 1952,104, 229-233. 

Piperidino-l, 2-propanediol carbanilate (ester), monohydrate 1, 2-Propanediol, 3-(l-piperidinyl)-, Z>w-(phenyl-carbamate) (ester), monohydrate U.S.P., N.F.,... 

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