Mebutamate

Mebutamate

Systematic (IUPAC) name
2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate
Clinical data
Legal status
Legal status	US: Schedule IV
Identifiers
CAS Number	64-55-1
ATC code	N05BC04 (WHO)
PubChem	CID 6151
ChemSpider	5919
UNII	5H8F175RER
KEGG	D01807
ChEMBL	CHEMBL1200922
Chemical data
Formula	C10H20N2O4
Molar mass	232.277 g/mol
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) Key:LEROTMJVBFSIMP-UHFFFAOYSA-N
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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 GABA_A 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

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

Structural analogs

• Lorbamate
• Carisoprodol
• Pentabamate
• Mebutamate
• Meprobamate
• Felbamate
• Tybamate

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. 5813. ISBN 978-0-911910-00-1.
3. Tetreault, L.; Richer, P.; Bordeleau, J. M. (1967). "Hypnotic properties of mebutamate: A comparative study of mebutamate, secobarbital and placebo in psychiatric patients". Canadian Medical Association journal 97 (8): 395–398. PMC 1923261. PMID 6037393.