Structure via PubChem · Public domain (PubChem)
meprobamate
Sign in to saveMeprobamate—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 It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index (lower risk of toxicity at therapeutically prescribed doses) and lower incidence of serious side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.
Key facts
- Drug.N
- 2
- Drug.O
- 4
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 459508597
- Drug.IUPAC_name
- [2-(carbamoyloxymethyl)-2-methyl-pentyl] carbamate
- Drug.image
- Meprobamate.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Meprobamate ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Miltown, Equanil, Meprospan, Amepromat, Quivet, Zirponand, and many others
- Drug.MedlinePlus
- a682077
- Drug.pregnancy_AU
- C
- Drug.pregnancy_US
- D
- Drug.legal_AU
- S4
- Drug.legal_BR
- B1
- Drug.legal_US
- Schedule IV
- Drug.legal_CA
- Schedule IV
- Drug.legal_DE
- Anlage II
via Wikipedia infobox
Chemical data
- Formula
- C9H18N2O4
- Molecular weight
- 218.25 g/mol
- IUPAC name
- [2-(carbamoyloxymethyl)-2-methylpentyl] carbamate
- SMILES
- CCCC(C)(COC(=O)N)COC(=O)N
- InChIKey
- NPPQSCRMBWNHMW-UHFFFAOYSA-N
- XLogP
- 0.7
- Polar surface area
- 105 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
2,556 papers- Meprobamate.Clinical toxicology · 1981
- Meprobamate.Journal of the American Pharmaceutical Association · 1977
- Meprobamate addiction.Journal of the American Medical Association · 1958
- Meprobamate addiction.The New England journal of medicine · 1958
- [Meprobamate].Soins. Psychiatrie · 1984
via PubMed
Wikidata facts
- Mass
- 218.127
Show 5 more facts
- chemical formula
- C₉H₁₈N₂O₄
- defined daily dose
- 1.2
- World Health Organisation international non-proprietary name
- meprobamate
- canonical SMILES
- CCCC(C)(COC(=O)N)COC(=O)N
- Commons category
- Meprobamate
via Wikidata · CC0
~10 min read
Article
9 sectionsContents
- History
- Pharmacology
- Indications
- Side effects and overdose
- Health issues
- Synthesis
- See also
- References
- External links
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 It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index (lower risk of toxicity at therapeutically prescribed doses) and lower incidence of serious side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.
==History== Frank 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 (or myanesin) calmed laboratory rodents without actually sedating them. Berger subsequently referred to this “tranquilizing” effect in a now-historic article, published by the British Journal of Pharmacology in 1946. However, three major drawbacks existed to the use of mephenesin as a tranquilizer: a very short duration of action, greater effect on the spinal cord than on the brain (resulting in a very low therapeutic index), and a weak activity. thumb|Informational material advertising the prescription of meprobamate to children for anxiety disorders, [[stammering, tics and tantrums.]] 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 overcame these three drawbacks. Wallace Laboratories, a subsidiary of Carter Products, bought the license and named their new product "Miltown" after the borough of Milltown, New Jersey. Launched in 1955, it rapidly became the first blockbuster psychotropic drug in American history, becoming popular in Hollywood and gaining fame for its seemingly miraculous effects. It has since been marketed under more than 100 trade names, from Amepromat through Quivet to Zirpon.