Meprobamate Property

Melting point:

97-100°C

Boiling point:

358.93°C (rough estimate)

Density 

1.2004 (rough estimate)

refractive index 

1.4480 (estimate)

Flash point:

11 °C

storage temp. 

2-8°C

solubility 

DMF: 50 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 30 mg/ml; Ethanol: 25 mg/ml

pka

13.09±0.50(Predicted)

Water Solubility 

6.2g/L(25 ºC)

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

CAS DataBase Reference

57-53-4(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Propanediol, 2-methyl-2-propyl-, dicarbamate(57-53-4)

EPA Substance Registry System

Meprobamate (57-53-4)

Safety

Hazard Codes 

Xn,T,F

Risk Statements 

22-39/23/24/25-23/24/25-11

Safety Statements 

7-16-36/37-45

RIDADR 

UN 1230 3/PG 2

WGK Germany 

3

RTECS 

TZ0175000

HS Code 

2924110000

Hazardous Substances Data

57-53-4(Hazardous Substances Data)

Toxicity

LD50 i.p. in mice: 800 mg/kg (Berger)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Meprobamate Chemical Properties,Usage,Production

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)

General Description

Meprobamate,2-methyl-2-propyltrimethylene dicarbamate, 2-methyl-2-propyl-1,3-propanediol dicarbamate (Equanil, Miltown), is officiallyindicated as an antianxiety agent. It is also a sedative–hypnotic agent. It has several overall pharmacological properties resembling those of benzodiazepines and barbiturates.The mechanism of action underlying anxiolytic effectsis unknown but may involve effects on conductivity inspecific brain areas.It does not appear to act through effectson GABAergic systems.The drug is effective againstabsence seizures and may worsen generalized tonic–clonicseizures.

General Description

Odorless white crystalline powder. Bitter taste. Solutions in water are neutral or slightly acidic.

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.]