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Mebutamate

Summary

Mebutamate (Capla, Dormate) is an anxiolytic and sedative drug with antihypertensive effects of the carbamate class.[1][2] It has effects comparable to those of barbiturates such as secobarbital, but is only around 1/3 the potency of secobarbital as a sedative. Side effects include dizziness and headaches.[3]

Mebutamate
Clinical data
ATC code
Legal status
Legal status
Identifiers
  • 2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate
CAS Number
  • 64-55-1 ☒N
PubChem CID
  • 6151
ChemSpider
  • 5919 ☒N
UNII
  • 5H8F175RER
KEGG
  • D01807 checkY
ChEMBL
  • ChEMBL1200922 ☒N
CompTox Dashboard (EPA)
  • DTXSID1023239 Edit this at Wikidata
ECHA InfoCard100.000.534 Edit this at Wikidata
Chemical and physical data
FormulaC10H20N2O4
Molar mass232.280 g·mol−1
3D model (JSmol)
  • Interactive image
  • CCC(C)C(C)(COC(=O)N)COC(=O)N
  • InChI=1S/C10H20N2O4/c1-4-7(2)10(3,5-15-8(11)13)6-16-9(12)14/h7H,4-6H2,1-3H3,(H2,11,13)(H2,12,14) ☒N
  • Key:LEROTMJVBFSIMP-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Mebutamate is one of many GABAergic drugs which act via allosteric agonism of the GABAA receptor at the β-subreceptor similar to barbiturates. In contrast, benzodiazepines act at the α-subreceptor. As such, carbamates and barbiturates, possess analgesic properties while the benzodiazepine class of drugs are strictly psychoactive.

Other carbamates with the same mechanism of action and pharmacological properties include meprobamate, carisoprodol, felbamate, and tybamate.

Synthesis edit

 
Mebutamate synthesis: Berger, Ludwig, U.S. patent 2,878,280 (1959 to Carter Prod.).

Structural analogs edit

References edit

  1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 634. ISBN 978-3-88763-075-1.
  2. ^ The Merck Index (14 ed.). Merck Publishers. 2006-11-03. 5813. ISBN 978-0-911910-00-1.
  3. ^ Tetreault L, Richer P, Bordeleau JM (August 1967). "Hypnotic properties of mebutamate: a comparative study of mebutamate, secobarbital and placebo in psychiatric patients". Canadian Medical Association Journal. 97 (8): 395–8. PMC 1923261. PMID 6037393.