Mebutamate

Mebutamate
Clinical data
ATC code
Legal status
Legal status
  • US: Schedule IV
Identifiers
IUPAC name
  • 2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.534
Chemical and physical data
FormulaC10H20N2O4
Molar mass232.280 g·mol−1
3D model (JSmol)
SMILES
  • CCC(C)C(C)(COC(=O)N)COC(=O)N
InChI
  • 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 (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 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

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

Structural analogs

References

  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.
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