57-53-4 Usage
Description
Meprobamate, also known as 2-methyl-2-propyltrimethylene dicarbamate or 2-methyl-2-propyl-1,3-propanediol dicarbamate, is an anxiolytic and sedative-hypnotic agent. It is officially indicated as an antianxiety agent and has pharmacological properties resembling those of benzodiazepines and barbiturates. The mechanism of action underlying its anxiolytic effects is unknown but may involve effects on conductivity in specific brain areas. It does not appear to act through effects on GABAergic systems. Meprobamate is effective against absence seizures and may worsen generalized tonic-clonic seizures. It is an odorless white crystalline powder with a bitter taste, and its solutions in water are neutral or slightly acidic.
Uses
Used in Pharmaceutical Industry:
Meprobamate is used as an anxiolytic for treating anxiety disorders. It helps in reducing anxiety and promoting relaxation without causing drowsiness or significant sedation.
Used in Medical Field:
Meprobamate is used as a sedative-hypnotic agent for inducing sleep and treating insomnia. It is also effective against absence seizures and may be prescribed for this purpose.
Used in Controlled Substances:
Meprobamate is a controlled substance due to its potential for abuse and dependence. It is regulated to ensure that it is used appropriately and safely in medical settings.
Originator
Equanil,Wyeth,US,1955
Manufacturing Process
A solution containing 52.8 parts of 2-methyl-2-n-propyl-1,3-propanediol and 128 parts of acetone is added with stirring to 112 parts of liquid phosgene at such a rate that the temperature of the reaction is maintained at -5° to 0°C. The reaction is stirred one hour at about 0°C then cooled to -15°C. A cooled 30% solution of 32 parts of sodium hydroxide is added with stirring to the reaction at such a rate that the temperature is maintained at -15° to -5°C. The mixture is stirred for an additional ? hour at about 0°C then cooled to - 20°C. 180 parts of cooled ammonium hydroxide solution (28.6% NH3) are added while cooling and with stirring at such a rate that the temperature rises slowly to 20°C and stirring is continued for an additional ? hour. The mixture is poured with agitation into 1,700 parts of ice water. The solid which separates is removed by filtration and dried. Recrystallization from water gives 55 parts (63% of theoretical yield) of 2-methyl-2-n-propyl-1,3-propanediol dicarbamate, MP 104° to 105°C.
Therapeutic Function
Tranquilizer
World Health Organization (WHO)
Meprobamate, a bis-carbamate ester, was introduced in 1955 for
the treatment of anxiety and was subsequently used as a sedative-hypnotic drug.
Psychological and physical dependence can occur and abuse has been reported.
Meprobamate is controlled under Schedule IV of the 1971 Convention on
Psychotropic Substances.
(Reference: (UNCPS4) United Nations Convention on Psychotropic Substances (IV),
, , 1971)
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Meprobamate is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.
Hazard
Central nervous system depressant, use
restricted by law.
Fire Hazard
Flash point data for Meprobamate are not available; however, Meprobamate is probably combustible.
Clinical Use
Meprobamate is also a centrally acting skeletal musclerelaxant. The agents in this group find use in several conditions,such as strains and sprains that may produce acutemuscle spasm. They have interneuronal blocking propertiesat the level of the spinal cord, which are said to bepartly responsible for skeletal muscle relaxation.Also,the general CNS depressant properties they possess maycontribute to, or be mainly responsible for, the skeletalmuscle relaxant activity.
Safety Profile
Human poison by
unspecified routes. Moderately toxic to
humans and experimentally by ingestion.
Experimental poison by intravenous,
intraperitoneal, and subcutaneous routes. An
experimental teratogen. Human systemic
effects by ingestion: coma, blood pressure
decrease, regional or general arteriolar
constriction, dyspnea, cyanosis, respiratory
depression, nausea or vomiting, and allergic
skin dermatitis. Experimental reproductive
effects. Mutation data reported. Implicated
in aplastic anemia. Used as a tranquilizer.
When heated to decomposition it emits
toxic fumes of NOx.
Purification Methods
Crystallise it from hot water, aqueous EtOH (m 104-105.5o) or xylene (m 104.1-105.3o). It can be an addictive drug. [Beilstein 3 IV 73.]
Check Digit Verification of cas no
The CAS Registry Mumber 57-53-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 57-53:
(4*5)+(3*7)+(2*5)+(1*3)=54
54 % 10 = 4
So 57-53-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13)
57-53-4Relevant articles and documents
Iron-catalyzed reaction of urea with alcohols and amines: A safe alternative for the synthesis of primary carbamates
Pe?a-López, Miguel,Neumann, Helfried,Beller, Matthias
, p. 2233 - 2238 (2017/07/25)
A general study of the iron-catalyzed reaction of urea with nucleophiles is here presented. The carbamoylation of alcohols allows for the synthesis of N-unsubstituted (primary) carbamates, including present drugs (Felbamate and Meprobamat, without the necessity to apply phosgene and related derivatives. Using amines as nucleophiles gave rise to the respective mono-and disubstituted ureas via selective transamidation reaction. These atom-economical transformations provide a direct and selective access to valuable compounds from cheap and readily available urea using a simple Lewis-acidic iron(Icatalyst.
Pharmaceutical composition and process of treatment
-
, (2008/06/13)
A process for alleviating proliferative skin diseases such as psoriasis, atopic dermatitis, etc. comprising administering to humans, or domesticated animals, topically and/or systemically a composition comprising a pharmaceutical carrier and at least one active compound selected from the groups, substituted alkyl zanthines, tricyclic antidepressants, organic nitrates, antihypertensives, anti-asthma agents and central nervous system depressants and combinations of certain compounds from specifically named groups of compounds.
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