General Description
Odorless white crystalline powder. Bitter taste. Solutions in water are neutral or slightly acidic.
Reactivity Profile
MEPROBAMATE(57-53-4) 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.
Air & Water Reactions
Insoluble in water.
Hazard
Central nervous system depressant, use
restricted by law.
Fire Hazard
Flash point data for this chemical are not available; however, MEPROBAMATE is probably combustible.
Chemical Properties
white crystalline powder
Originator
Equanil,Wyeth,US,1955
Uses
An anxiolytic.
This is a controlled substance.
Definition
ChEBI: Meprobamate is an organic molecular entity.
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.
Brand name
Amosene (Ferndale); Bamate (Alra); Equanil (Wyeth); Mepriam
(Teva); Meprospan (Medpointe); Miltown (Medpointe);
Neuramate (Halsey); Tranmep (Solvay Pharmaceuticals);3p bamte;Apo-meprobamate;Carb-a-med;Clindoorm;Cusitan;Daritran;Detensitral;Dolovisano;Dormilfo n;Dystoid;Edental;Equiner;Equqtrqte;Gene-bamate;Idemin;Indemin;Irs 109 a;Iterco;Juvamidon;Lan-dol;Lenicor;M.a.s.;M.p. trantabs;Margaris;Meditran;Mep-e;Meprobadal;Meprobil;Meprogesic q;Meprolin;Mepronel;Mepro-secergan 400;Meproserpina;Meprospan 400;Meproten;Meproyrin;Meprozine;Meriprobate;Microbamat;Midixin;Milspan;Miltown s-r;Neo-nervostal;Neo-tran;Neurocalm;Novomato;Novomepro;Nyktogen;Oasil procalmadiol;Odsil 10;Panquil;Pensive;Pentaneural;Pm 2;Pmb 4000;Prequil;Probal;Probasan;Probromato;Psico-retard;Quietidon;Regium;Seda baxacor;Sedavier;Selene;Selodorm;Serenade;Sintown;Sopanil;Spasmobamat;Tcm 200;Tcm 400;Trankilin;Trelmar;Tri-reumo-campil;Vasocalm;Vistabamate;Wescomep.
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)
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.
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.]
