Tybamate

Tybamate

Clinical data
ATC code	none
Identifiers
IUPAC name [2-(Carbamoyloxymethyl)-2-methylpentyl] N-butylcarbamate
CAS Number	4268-36-4 Y
PubChem CID	20266
ChemSpider	19092 Y
UNII	3875LLL8M8
KEGG	D06260 Y
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C13H26N2O4
Molar mass	274.361 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCNC(=O)OCC(C)(CCC)COC(=O)N
InChI InChI=1S/C13H26N2O4/c1-4-6-8-15-12(17)19-10-13(3,7-5-2)9-18-11(14)16/h4-10H2,1-3H3,(H2,14,16)(H,15,17) Y Key:PRBORDFJHHAISJ-UHFFFAOYSA-N Y

Tybamate (INN; Solacen, Tybatran, Effisax) is an anxiolytic of the carbamate family. It is a prodrug for meprobamate in the same way as the better known drug carisoprodol. It has liver enzyme inducing effects similar to those of phenobarbital but much weaker.

As the trade name Tybatran (Robins), it was formerly available in capsules of 125, 250, and 350 mg, taken 3 or 4 times a day for a total daily dosage of 750 mg to 2 g. The plasma half-life of the drug is three hours. At high doses in combination with phenothiazines, it could produce convulsions.

Synthesis

Catalytic hydrogenation of 2-methyl-2-pentenal (1) gives the aldehyde 2-methylpentanal (2). Treatment with formaldehyde gives a crossed Cannizzaro reaction yielding 2,2-bis(hydroxymethyl)pentane (3). Cyclisation of this diol with diethyl carbonate gives (4), which reacts with ammonia to provide the carbamate (5). Lastly, treatment with butyl isocyanate (6) produces tybamate.