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meprobamate

Structure via PubChem · Public domain (PubChem)

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meprobamate

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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 It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index (lower risk of toxicity at therapeutically prescribed doses) and lower incidence of serious side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.

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

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
Sources (5)

via Wikidata · CC0

~10 min read

Article

9 sections
Contents
  • 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 It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index (lower risk of toxicity at therapeutically prescribed doses) and lower incidence of serious side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.

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