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Mebutamate

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Chemical compound
Pharmaceutical compound
Mebutamate
Clinical data
ATC code
Legal status
Legal status
Identifiers
  • 2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.000.534Edit this at Wikidata
Chemical and physical data
FormulaC10H20N2O4
Molar mass232.280 g·mol−1
3D model (JSmol)
  • 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 (Capla,Dormate) is ananxiolytic andsedativedrug withantihypertensive effects of the carbamate class.[1][2] It has effects comparable to those ofbarbiturates such assecobarbital, but is only around 1/3 the potency of secobarbital as a sedative. Side effects includedizziness andheadaches.[3]

Mebutamate is one of manyGABAergic drugs which act viaallosteric agonism of theGABAA receptor at the β-subreceptor similar to barbiturates. In contrast,benzodiazepines act at the α-subreceptor. As such, carbamates and barbiturates, possessanalgesic properties while the benzodiazepine class of drugs are strictly psychoactive.

Other carbamates with the same mechanism of action and pharmacological properties includemeprobamate,carisoprodol,felbamate, andtybamate.

Synthesis

[edit]
Mebutamate synthesis: Berger, Ludwig,U.S. patent 2,878,280 (1959 toCarter 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.
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