Trimethobenzamide

Quality 0.50 · 2 views · Updated 2 months ago

Antiemetic medication

title: "Trimethobenzamide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antiemetics", "benzamides", "d2-antagonists", "phenol-ethers"] description: "Antiemetic medication" topic_path: "general/antiemetics" source: "https://en.wikipedia.org/wiki/Trimethobenzamide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Antiemetic medication ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470615098 | IUPAC_name = N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}- 3,4,5-trimethoxy-benzamide | image = Trimethobenzamide2DACS.svg | image_class = skin-invert-image | image2 = Trimethobenzamidefinal.png | image_class2 = bg-transparent | width = 250px | tradename = Tigan, Tebamide | Drugs.com = | MedlinePlus = a682693 | pregnancy_AU = | pregnancy_US = C | legal_AU = | legal_UK = | legal_US = Rx-only | routes_of_administration = Oral, rectal, intramuscular | bioavailability = 60-100% | elimination_half-life = 7 to 9 hours (mean) | excretion = urine (30-50%), faeces | IUPHAR_ligand = 7614 | CAS_number_Ref = | CAS_number = 138-56-7 | ATC_prefix = R06 | ATC_suffix = AA10 | PubChem = 5577 | DrugBank_Ref = | DrugBank = DB00662 | ChemSpiderID_Ref = | ChemSpiderID = 5375 | UNII_Ref = | UNII = W2X096QY97 | ChEBI_Ref = | ChEBI = 27796 | ChEMBL_Ref = | ChEMBL = 1201256 | C=21 | H=28 | N=2 | O=5 | smiles = O=C(c1cc(OC)c(OC)c(OC)c1)NCc2ccc(OCCN(C)C)cc2 | StdInChI_Ref = | StdInChI = 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) | StdInChIKey_Ref = | StdInChIKey = FEZBIKUBAYAZIU-UHFFFAOYSA-N

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. 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.

Formulations

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.

Synthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/9/93/Trimethobenzamide_synthesis.svg" caption="2879293}} (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).

References

(2012). "Dopamine receptor antagonists". Ann Palliat Med.
Waknine, Yael. (September 2016). "FDA Bans Suppositories With Trimethobenzamide". [[Medscape]]}}{{dead link.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::