|Trade names||Tigan, Tebamide, others|
|Main uses||Nausea, vomiting|
|Side effects||Blurry vision, sleepiness, muscle cramps|
|By mouth, rectal, intramuscular|
|Onset of action||Within 40 min|
|Duration of action||Up to 4 hrs|
|Elimination half-life||7 to 9 hours (mean)|
|Excretion||Urine (30-50%), faeces|
|Chemical and physical data|
|Molar mass||388.464 g·mol−1|
|3D model (JSmol)|
Trimethobenzamide, sold under the brand name Tigan among others, is a medication used to treat nausea and vomiting. This includes that due to surgery and gastroenteritis. It is taken by mouth or by injection into a muscle. Onset occurs within 40 minutes and lasts up to 4 hours.
Common side effects include blurry vision, sleepiness, and muscle cramps. Other side effects may include liver problems and allergic reactions. Safety in pregnancy and breastfeeding is unclear. Use in children with viral infections is not recommended due to concerns of Reye syndrome. It is an antihistamine and believed to work by blocking the chemoreceptor trigger zone.
The typical dose is 300 mg by mouth 3 to 4 times per day or 200 mg by injection 3 to 4 times per day.
Mechanism of action
Society and culture
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).
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