Meprobamate

Meprobamate
Clinical data
Trade namesMiltown, Equanil, Meprospan, Amepromat, Quivet, Zirponand, and many others
AHFS/Drugs.comMonograph
MedlinePlusa682077
Pregnancy
category
  • AU: C
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability?
MetabolismHepatic
Elimination half-life10 hours
ExcretionRenal
Identifiers
  • [2-(carbamoyloxymethyl)-2-methyl-pentyl] carbamate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.306 Edit this at Wikidata
Chemical and physical data
FormulaC9H18N2O4
Molar mass218.253 g·mol−1
3D model (JSmol)
Density1.229 g/cm3
Melting point105 to 106 °C (221 to 223 °F)
Boiling point200 °C (392 °F) to 210 °C (410 °F)
  • O=C(N)OCC(C)(CCC)COC(N)=O
  • InChI=1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13) checkY
  • Key:NPPQSCRMBWNHMW-UHFFFAOYSA-N checkY
  (verify)

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 It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index (lower risk of toxicity at therapeutically prescribed doses) and lower incidence of serious side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

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.