Mebutamate

Mebutamate
Clinical data
ATC code	N05BC04 (WHO) ;
Legal status
Legal status	US: Schedule IV;
Identifiers
	IUPAC name 2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate;
CAS Number	64-55-1 ;
PubChem CID	6151;
ChemSpider	5919 ;
UNII	5H8F175RER;
KEGG	D01807 ;
ChEMBL	ChEMBL1200922 ;
CompTox Dashboard (EPA)	DTXSID1023239 ;
ECHA InfoCard	100.000.534
Chemical and physical data
Formula	C10H20N2O4
Molar mass	232.280 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(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 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 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

^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 634. ISBN 978-3-88763-075-1.
^ The Merck Index (14 ed.). Merck Publishers. 2006-11-03. 5813. ISBN 978-0-911910-00-1.
^ 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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[TaylorFrancis2000-1] 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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Clinical data

ATC code	N05BC04 (WHO)
Legal status
Legal status	US: Schedule IV
Identifiers
IUPAC name 2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate
CAS Number	64-55-1^N
PubChem CID	6151
ChemSpider	5919^N
UNII	5H8F175RER
KEGG	D01807^Y
ChEMBL	ChEMBL1200922^N
CompTox Dashboard (EPA)	DTXSID1023239
ECHA InfoCard	100.000.534
Chemical and physical data
Formula	C₁₀H₂₀N₂O₄
Molar mass	232.280 g·mol⁻¹
3D model (JSmol)	Interactive image
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)