Last updated
Clinical data
Trade names Tigan, Tebamide
AHFS/ Monograph
MedlinePlus a682693
Routes of
Oral, rectal, intramuscular
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 60-100%
Elimination half-life 7 to 9 hours (mean)
Excretion urine (30-50%), faeces
  • N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}-
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.848 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H28N2O5
Molar mass 388.464 g·mol−1
3D model (JSmol)
  • O=C(c1cc(OC)c(OC)c(OC)c1)NCc2ccc(OCCN(C)C)cc2
  • InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24) Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting.


Mechanism of action

Trimethobenzamide is an antagonist of the D2 receptor. [1] It is believed to affect the chemoreceptor trigger zone (CTZ) of the medulla oblongata to suppress nausea and vomiting.

Side effects

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. [2]


Trimethobenzamide synthesis: Hoffmann La Roche, U.S. Patent 2,879,293 (1959). Trimethobenzamide synthesis.svg
Trimethobenzamide synthesis: Hoffmann La Roche, U.S. Patent 2,879,293 (1959).

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).

See also

Related Research Articles

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  1. Smith HS, Cox LR, Smith BR (2012). "Dopamine receptor antagonists". Ann Palliat Med. 1 (2): 137–42. doi:10.3978/j.issn.2224-5820.2012.07.09. PMID   25841474.
  2. Waknine, Yael (April 6, 2007). "FDA Bans Suppositories With Trimethobenzamide". Medscape . Retrieved 2007-04-06.[ dead link ]