Mebutamate

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Mebutamate
File:Mebutamate.svg
Systematic (IUPAC) name
2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate
Clinical data
Legal status
Identifiers
CAS Number 64-55-1 N
ATC code N05BC04 (WHO)
PubChem CID: 6151
ChemSpider 5919 N
UNII 5H8F175RER YesY
KEGG D01807 YesY
ChEMBL CHEMBL1200922 N
Chemical data
Formula C10H20N2O4
Molecular mass 232.277 g/mol
  • 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
 NYesY (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 which the benzodiazepine class of drugs do not.

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

Synthesis

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

Structural analogs

References

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