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57-53-4

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Basic Information
CAS No.: 57-53-4
Name: Meprobamate
Article Data: 22
Molecular Structure:
Molecular Structure of 57-53-4 (Meprobamate)
Formula: C9H18 N2 O4
Molecular Weight: 218.253
Synonyms: 1,3-Propanediol,2-methyl-2-propyl-, dicarbamate (8CI,9CI); 2,2-Di(carbamoyloxymethyl)pentane;2-Methyl-2-n-propyl-1,3-propanediol dicarbamate;2-Methyl-2-propyl-1,3-propanediol dicarbamate; Amepromat; Amosene; Anastress;Anatimon; Andaxin; Aneural; Ansiatan; Anzil; Apascil; Appetrol; Arcoban;Artolon; Atraxin; Ayeramate; Bamo 400; Biobamat; Biobamate; Calmax; Calmiren;Canquil-400; Cap-O-Tran; Carb-A-Med; Carbamic acid2-methyl-2-propyltrimethylene ester; Carbaxin; Cirpon; Crestanil; Cyrpon;Dicandiol; Diron; Ecuanil; Epikur; Equanil; Equanil Suspension; Equinil;Fas-Cile 200; Gadexyl; Harmonin; Hartol; Holbamate; Kesso-Bamate; Klort;Larten; Lepetown; Libiolan; Mar-Bate; Mepantin; Mepavlon; Meposed; Mepr;Meprin; Meprindon; Meprobam; Meprobamat; Meprobamat-Petrasch; Meprobamate;Meproban; Meprocompren; Meprocon CMC; Meprol; Mepronil; Meprosin; Meprospan;Meprotabs; Meprotan; Meproten; Meprotil; Meptran; Mesmar; Metranquil;Micrainin; Microbamat; Milprem; Miltaun; Miltown; Miltrate; Morbam; My-trans;NSC 30418; Nervonus; Oasil; PMB 200; PMB 400; Panediol; Perequil; Perquietil;Pertranquil; Placidon; Placitate; Probamyl; Procalmadiol; Procalmidol; Promate;Protran; Quaname; Quanil; Rastenil; Reostral; Restenil; Robamate; Sedanil;Sedazil; Seril; Setran; Sowell; Tamate; Trankvilan; Tranlisant; Tranquilan;Tranquilax; Tranquiline; Urbil; Urbilat; Vio-Bamate
EINECS: 200-337-5
Density: 1.139g/cm3
Melting Point: 104 - 106 C
Boiling Point: 434.2°Cat760mmHg
Flash Point: 229.7°C
Solubility: negligible
Appearance: white crystalline powder
Hazard Symbols:
Risk Codes: R22   
Safety: 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. See also CARBAMATES.
PSA: 104.64000
LogP: 2.38400
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Chemistry

Empirical Formula: C9H18N2O4
Molecular Weight: 218.2502 
EINECS: 200-337-5 
Index of Refraction: 1.479
Density: 1.139 g/cm3
Flash Point: 229.7 °C
Storage temp: 2-8°C
Enthalpy of Vaporization: 69.03 kJ/mol
Boiling Point: 434.2 °C at 760 mmHg
Vapour Pressure: 9.64E-08 mmHg at 25 °C
Structure of Meprobamate (CAS NO.57-53-4):
             

History

 Meprobamate (CAS NO.57-53-4) was first synthesized by Bernard John Ludwig, PhD, and Frank Milan Berger, MD, at Carter Products in May 1950. And, it rapidly became the first blockbuster psychotropic drug in American history, gaining notoriety for its seemingly miraculous effects and becoming popular in Hollywood. In the mid-1940s, Dr. Berger was working in a laboratory of a British drug company for looking for a preservative for penicillin. After moving to Wallace Laboratories in New Jersey, Dr. Berger and a chemist, Dr. Bernard Ludwig, synthesized a chemically-related tranquilizing compound, meprobamate, that was able to overcome these three drawbacks. A December 1955 study of 101 patients at the Mississippi State Hospital in Whitfield, Mississippi, found meprobamate useful in the alleviation of "mental symptoms."In April 1965 meprobamate was removed from the list of tranquilizers when experts ruled that the drug was a sedative instead. The significance of meprobamate and the benzodiazepines lies in the fact that these drugs, despite being habit-forming, essentially replaced the widely-used and potentially-lethal class of sedatives.

Uses

 Meprobamate (CAS NO.57-53-4) is used as an anxiolytic drug. It can be used as a weak antipsychotic for the treatment of neurosis nervous insomnia.

Production

Take 2 - Methyl-amyl aldehydes with Formaldehyde for the reaction of aldol condensation to get 2 - Methyl -2 - propyl propylene glycol , and then having the reaction withe Phosgene and Ammonia, or with Sodium cyanate and Hydrochloric acid to derive: Meprobamate (CAS NO.57-53-4).

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 80mg/kg (80mg/kg) BEHAVIORAL: COMA Human Toxicology. Vol. 4, Pg. 215, 1985.
guinea pig LD50 subcutaneous 380mg/kg (380mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962.
hamster LD50 intraperitoneal 625mg/kg (625mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
BEHAVIORAL: MUSCLE WEAKNESS
BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
hamster LD50 oral 1410mg/kg (1410mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
BEHAVIORAL: ATAXIA
BEHAVIORAL: MUSCLE WEAKNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
human TDLo oral 280mg/kg (280mg/kg) BEHAVIORAL: COMA
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Ohio State Medical Journal. Vol. 52, Pg. 1304, 1956.
man LDLo unreported 441mg/kg (441mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo oral 5700ug/kg (5.7mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA
GASTROINTESTINAL: NAUSEA OR VOMITING
SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
Journal of the Irish Medical Association. Vol. 41, Pg. 119, 1957.
man TDLo oral 114mg/kg (114mg/kg) BEHAVIORAL: COMA
CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
mouse LD50 intraperitoneal 331mg/kg (331mg/kg)   Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 23, Pg. 281, 1971.
mouse LD50 intravenous 230mg/kg (230mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 12, Pg. 447, 1977.
mouse LD50 oral 750mg/kg (750mg/kg)   Journal of Medicinal Chemistry. Vol. 15, Pg. 998, 1972.
mouse LD50 subcutaneous 520mg/kg (520mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 26, Pg. 109, 1974.
rabbit LD50 intravenous 260mg/kg (260mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
BEHAVIORAL: REGIDITY
International Journal of Neuropharmacology. Vol. 5, Pg. 305, 1966.
rat LD50 intraperitoneal 410mg/kg (410mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
BEHAVIORAL: MUSCLE WEAKNESS
BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
rat LD50 intravenous 350mg/kg (350mg/kg) BEHAVIORAL: MUSCLE WEAKNESS
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Prensa Medica Argentina. Vol. 44, Pg. 915, 1957.
rat LD50 oral 794mg/kg (794mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 93, 1971.
rat LD50 subcutaneous 525mg/kg (525mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 56, Pg. 377, 1960.
women LDLo oral 760mg/kg (760mg/kg) BEHAVIORAL: COMA JAMA, Journal of the American Medical Association. Vol. 207, Pg. 361, 1969.
women TDLo oral 112mg/kg (112mg/kg) BEHAVIORAL: ATAXIA
BEHAVIORAL: COMA
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
 
women TDLo oral 120mg/kg (120mg/kg) BEHAVIORAL: COMA
CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
women TDLo oral 240mg/kg (240mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
BEHAVIORAL: COMA
VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
women TDLo oral 360mg/kg (360mg/kg) BEHAVIORAL: COMA
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
women TDLo oral 384mg/kg (384mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
VASCULAR: REGIONAL OR GENERAL ARTERIOLAR CONSTRICTION
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Northwest Medicine. Vol. 56, Pg. 321, 1957.
 

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

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. See also CARBAMATES.
 

Hazard Codes: HarmfulXn ToxicTFlammableF
Risk Statements: 22-39/23/24/25-23/24/25-11 
R11:Highly flammable. 
R22:Harmful if swallowed. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R39:Danger of very serious irreversible effects.
Safety Statements: 7-16-36/37-45 
S7:Keep container tightly closed. 
S16:Keep away from sources of ignition. 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

Specification

 Meprobamate ,its cas register number is 57-53-4. It also can be called Miltown ; Equanil ; Meprospan ; Tranmep and 1,3-Propanediol, 2-methyl-2-propyl-, dicarbamate . It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines. It is a carbamate derivative. Although it was the best-selling minor tranquilizer for a time, it has largely been replaced by the benzodiazepines. Meprobamate has most of the pharmacological effects and dangers of the barbiturates and is licensed for the short-term relief of anxiety, although it is not known whether the purported anti-anxiety effects of meprobamate are separable from its sedative effects.