|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||388.464 g·mol−1|
|3D model (JSmol)|
|(what is this?)|
Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting.
Trimethobenzamide is an antagonist of the D2 receptor. It is believed to affect the chemoreceptor trigger zone (CTZ) of the medulla oblongata to suppress nausea and vomiting.
Possible side effects include drowsiness, dizziness, headache, muscle cramps, and blurred vision. More serious adverse effects include skin rash, tremors, parkinsonism, and jaundice.
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.
Trimethobenzamide was also available as a rectal suppository, but such formulations were banned by the U.S. Food and Drug Administration on April 6, 2007 due to unproven efficacy.
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).