Mebutamate

Mebutamate

File:Mebutamate.svg
Systematic (IUPAC) name
2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate
Clinical data
Legal status	US: Schedule IV
Identifiers
CAS Number	64-55-1 N
ATC code	N05BC04 (WHO)
PubChem	CID: 6151
ChemSpider	5919 N
UNII	5H8F175RER Y
KEGG	D01807 Y
ChEMBL	CHEMBL1200922 N
Chemical data
Formula	C10H20N2O4
Molecular 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) N Key:LEROTMJVBFSIMP-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Mebutamate (Capla, Dormate) is an anxiolytic and sedative drug with antihypertensive effects of the carbamate class. 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.

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

File:Mebutamate synthesis.svg

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

Structural analogs

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