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Meprobamate information


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
  • N05BC01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class B1 (Psychoactive drugs)[1]
  • CA: Schedule IV
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class C
  • US: Schedule IV
Pharmacokinetic data
Bioavailability?
MetabolismHepatic
Elimination half-life10 hours
ExcretionRenal
Identifiers
IUPAC name
  • [2-(carbamoyloxymethyl)-2-methyl-pentyl] carbamate
CAS Number
  • 57-53-4 checkY
PubChem CID
  • 4064
IUPHAR/BPS
  • 7225
DrugBank
  • DB00371 checkY
ChemSpider
  • 3924 checkY
UNII
  • 9I7LNY769Q
KEGG
  • D00376 checkY
ChEMBL
  • ChEMBL979 checkY
CompTox Dashboard (EPA)
  • DTXSID3023261 Edit this at Wikidata
ECHA InfoCard100.000.306 Edit this at Wikidata
Chemical and physical data
FormulaC9H18N2O4
Molar mass218.253 g·mol−1
3D model (JSmol)
  • Interactive image
Density1.229 g/cm3
Melting point105 to 106 °C (221 to 223 °F)
Boiling point200 °C (392 °F) to 210 °C (410 °F)
SMILES
  • O=C(N)OCC(C)(CCC)COC(N)=O
InChI
  • 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 It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index (lower risk of toxicity at therapeutically prescribed doses) and lower incidence of serious side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.

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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...

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Carisoprodol

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of its effects are believed to occur following being converted into meprobamate. Carisoprodol was approved for medical use in the United States in 1959...

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Emylcamate

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the treatment of anxiety and tension. It was claimed to be superior to meprobamate, which would eventually replace emylcamate. A study of the drug's effects...

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Antispasmodic

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prescription. Carisoprodol is similar to meprobamate as they both belong to the carbamate drug class and meprobamate is a clinically significant active metabolite...

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ATC code N05

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N05BB51 Hydroxyzine, combinations N05BC01 Meprobamate N05BC03 Emylcamate N05BC04 Mebutamate N05BC51 Meprobamate, combinations N05BD01 Benzoctamine N05BE01...

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Chlordiazepoxide

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tests for muscle relaxant activity using myanesin as a standard and then meprobamate and chlorpromazine when they became available. All compounds submitted...

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Medication

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"triphasic" pill Stimulants: methylphenidate, amphetamine Tranquilizers: meprobamate, chlorpromazine, reserpine, chlordiazepoxide, diazepam, and alprazolam...

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Phenprobamate

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similar to barbiturates. Its mechanism of action is probably similar to meprobamate. Phenprobamate has been used in humans as an anxiolytic, and is still...

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Schedule X

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Barbital Cyclobarbital Dexamphetamine Ethchlorvynol Glutethimide Ketamine Meprobamate Methamphetamine Methylphenidate Methylphenobarbital Pentobarbital Phencyclidine...

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Prenderol

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anticonvulsant and muscle relaxant effects. It is closely related in structure to meprobamate and numerous other alkyl alcohols and diols with generally comparable...

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Sedative

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Clonidine (Catapres, Kapvay) Cyclobenzaprine Gabapentin (Neurontin) Meprobamate Metaxalone (Skelaxin) Methocarbamol (Robaxin) Orphenadrine Phenibut Pregabalin...

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Methocarbamol

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the presence of other CNS depressants. Unlike other carbamates such as meprobamate and its prodrug carisoprodol, methocarbamol has greatly reduced abuse...

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Mebutamate

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pharmacological properties include meprobamate, carisoprodol, felbamate, and tybamate. Lorbamate Carisoprodol Pentabamate Meprobamate Felbamate Tybamate Index Nominum...

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List of psychiatric medications

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Lorazepam, Loxapine, Lumateperone, Lurasidone Maprotiline, Melperone, Meprobamate, Mesoridazine, Methamphetamine, Methaqualone, Methylphenidate, Mianserin...

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Mephenesin

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the inspiration for the synthesis of a derivative of 1,3-propanediol, meprobamate, by Bernard Ludwig and Frank Berger, the first tranquilizer to see widespread...

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Methaqualone

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Triazolam Carbamates Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate Imidazoles Etomidate Metomidate...

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Frank Berger

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June 1913 - 18 March 2008) was a Czech pharmacologist. He discovered meprobamate, carisoprodol, and felbamate, while working at Wallace Laboratories....

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Benactyzine

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there was some tentative evidence of effectiveness when combined with meprobamate, with the medication no longer available it is not clinically important...

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Ketamine

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Kynurenine L-689560 L-701324 Licostinel (ACEA-1021) LU-73068 MDL-105519 Meprobamate MRZ 2/576 PNQX Rapastinel (GLYX-13) ZD-9379; Polyamine site antagonists:...

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Mechanism of action

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Armodafinil Cannabidiol Cyclobenzaprine Demeclocycline Fabomotizole Lithium Meprobamate Methocarbamol Paracetamol Phenytoin PRL-8-53 Metformin Thalidomide In...

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Brazilian Controlled Drugs and Substances Act

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Lefetamine Ethyl loflazepate Loprazolam Lorazepam Lormetazepam Medazepam Meprobamate Mesocarb Methylphenobarbital (prominal) Methyprylon Midazolam Modafinil...

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Trazodone

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Others: Alpidem‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone‡ Ethanol (alcohol) Etifoxine Hypnotics Zopiclone...

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Sertraline

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Others: Alpidem‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone‡ Ethanol (alcohol) Etifoxine Hypnotics Zopiclone...

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Diphenhydramine

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Triazolam Carbamates Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate Imidazoles Etomidate Metomidate...

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Zopiclone

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Triazolam Carbamates Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate Imidazoles Etomidate Metomidate...

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Tybamate

Last Update:

Effisax) is an anxiolytic of the carbamate family. It is a prodrug for meprobamate in the same way as the better known drug carisoprodol. It has liver enzyme...

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Pregabalin

Last Update:

Others: Alpidem‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone‡ Ethanol (alcohol) Etifoxine Hypnotics Zopiclone...

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Bruce Lee

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day of his death, which contained both aspirin and the tranquilizer meprobamate, although he had taken it many times before. Although there was initial...

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