Meprobamate
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| Clinical data | |
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| Trade names | Miltown, Equanil, Meprospan, Amepromat, Quivet, Zirponand, and many others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682077 |
| Pregnancy category |
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| Routes of administration |
Oral |
| ATC code | N05BC01 (WHO) |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | Hepatic |
| Biological half-life | 10 hours |
| Excretion | Renal |
| Identifiers | |
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| CAS Number |
57-53-4 
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| PubChem (CID) | 4064 |
| IUPHAR/BPS | 7225 |
| DrugBank |
DB00371
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| ChemSpider |
3924
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| UNII |
9I7LNY769Q
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| KEGG |
D00376
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| ChEMBL |
CHEMBL979
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| ECHA InfoCard | 100.000.306 |
| Chemical and physical data | |
| Formula | C9H18N2O4 |
| Molar mass | 218.250 g/mol |
| 3D model (Jmol) | Interactive image |
| Density | 1.229 g/cm3 |
| Melting point | 105 to 106 °C (221 to 223 °F) |
| Boiling point | 200 °C (392 °F) to 210 °C (410 °F) |
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Meprobamate — marketed as Miltown by Wallace Laboratories and Equanil by Wyeth, among others — is a carbamate derivative used as an anxiolytic drug. It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index (lower risk of toxicity at therapeutically prescribed doses) and lower incidence of serious side effects.
In the mid-1940s, Frank Milan Berger was working in a laboratory of a British drug company, looking for a preservative for penicillin, when he noticed that a compound called mephenesin had a sedative effect in laboratory rodents. Berger subsequently referred to this sedating or “tranquilizing” effect in a now-historic article, published by The British Journal of Pharmacology in 1946. However, there were three major drawbacks to the use of mephenesin as a tranquilizer: a very short duration of action, greater effect on the spinal cord than on the brain, and a weak activity. In May 1950, after moving to Carter Products in New Jersey, Berger and a chemist, Bernard John Ludwig, synthesized a chemically related tranquilizing compound, meprobamate, that was able to overcome these three drawbacks. Wallace Laboratories, a subsidiary of Carter Products, bought the license and named their new product "Miltown" after the borough of Milltown in New Jersey. Launched in 1955, it rapidly became the first blockbuster psychotropic drug in American history, becoming popular in Hollywood and gaining notoriety for its seemingly miraculous effects. It has since been marketed under more than 100 trade names, from Amepromat through Quivet to Zirpon.
A December 1955 study of 101 patients at the Mississippi State Hospital in Whitfield, Mississippi, found meprobamate useful in the alleviation of "mental symptoms." Three percent of the patients made a complete recovery, 29% were greatly improved, and 50% were somewhat better. Eighteen percent realized little change. Self-destructive patients became cooperative and calmer, and experienced a resumption of logical thinking. In 50% of the cases relaxation brought about more favorable sleep habits. Hydrotherapy and all types of shock treatment were halted. Meprobamate was found to help in the treatment of alcoholics by 1956. By 1957, over 36 million prescriptions had been filled for meprobamate in the US alone, a billion pills had been manufactured, and it accounted for fully a third of all prescriptions written. Berger, clinical director of Wallace Laboratories (who died on March 16, 2008, aged 94), described it as a relaxant of the central nervous system, whereas other tranquilizers suppressed it. A University of Michigan study found that meprobamate affected driving skills. Though patients reported being able to relax more easily, meprobamate did not completely alleviate their tense feelings. The disclosures came at a special scientific meeting at the Barbizon Plaza Hotel in New York City, at which Aldous Huxley addressed an evening session. He predicted the development of many chemicals "capable of changing the quality of human consciousness", in the next few years.
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Wikipedia