Tybamate (INN; Solacen, Tybatran, Effisax) is an anxiolytic of the carbamate family.[1] 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.[2]
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| ECHA InfoCard | 100.022.050  |
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| Formula | C13H26N2O4 |
| Molar mass | 274.361 g·mol−1 |
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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.[3]
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.[4][5][6]
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