|Trade names||Tigan, Tebamide|
|Oral, rectal, intramuscular|
|Elimination half-life||7 to 9 hours (mean)|
|Excretion||urine (30-50%), faeces|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||388.458 g/mol g·mol−1|
|3D model (JSmol)|
|(what is this?)|
Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting. It is often prescribed for patients with gastroenteritis, medication-induced nausea, and other illnesses. Trimethobenzamide is generally considered the most potent antiemetic that does not have effects on the serotonergic, dopaminergic, or histaminergic systems, so it has a lower likelihood of causing undesired side effects. In the United States, it requires a prescription.
Mechanism of action
Trimethobenzamide is marketed under the brand names Tebamide and Tigan, manufactured by GlaxoSmithKline and King Pharmaceuticals, respectively. It is available as oral capsules and injectable formulations.
Alkylation of the sodium salt of p-hydroxybenzaldehyde (1) with 2-dimethylaminoethyl chloride affords the ether (2). Reductive amination of the aldehyde in the presence of ammonia gives diamine (3). Acylation of that product with 3,4,5-trimethoxybenzoyl chloride affords trimethobenzamide (4).