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MedKoo Cat#: 318952 | Name: Trimethobenzamide HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Trimethobenzamide 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. Although the specific mechanism through which trimethobenzamide functions is unknown, it is believed to affect the chemoreceptor trigger zone (CTZ) of the medulla oblongata.

Chemical Structure

Trimethobenzamide HCl
Trimethobenzamide HCl
CAS# 554-92-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 318952

Name: Trimethobenzamide HCl

CAS#: 554-92-7 (HCl)

Chemical Formula: C21H29ClN2O5

Exact Mass: 0.0000

Molecular Weight: 424.92

Elemental Analysis: C, 59.36; H, 6.88; Cl, 8.34; N, 6.59; O, 18.83

Price and Availability

Size Price Availability Quantity
100mg USD 265.00 2 weeks
500mg USD 650.00 2 weeks
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Related CAS #
554-92-7 (HCl) 138-56-7 (free base)
Synonym
Tebamide; Ticon; Tigan; trimethobenzamide; trimethobenzamide monohydrochloride; trade names Tebamide, Tigan.
IUPAC/Chemical Name
N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}-3,4,5-trimethoxy-benzamide hydrochloride
InChi Key
WIIZEEPFHXAUND-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H28N2O5.ClH/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);1H
SMILES Code
O=C(NCC1=CC=C(OCCN(C)C)C=C1)C2=CC(OC)=C(OC)C(OC)=C2.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related CAS# CAS#554-92-7 ( Trimethobenzamide HCl salt); CAS#138-56-7 ( Trimethobenzamide free base).

Preparing Stock Solutions

The following data is based on the product molecular weight 424.92 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Hauser RA, Isaacson S, Clinch T; Tigan/Apokyn Study Investigators. Randomized, placebo-controlled trial of trimethobenzamide to control nausea and vomiting during initiation and continued treatment with subcutaneous apomorphine injection. Parkinsonism Relat Disord. 2014 Nov;20(11):1171-6. doi: 10.1016/j.parkreldis.2014.08.010. Epub 2014 Aug 27. PubMed PMID: 25239603. 2: Goksu Erol AY, Gokcimen A, Ozdemir O. Growth failure, tardive dyskinesia, megacolon development, and hepatic damage in neonatal rats following exposure to trimethobenzamide in utero. J Matern Fetal Neonatal Med. 2011 Sep;24(9):1176-80. doi: 10.3109/14767058.2010.536867. Epub 2010 Dec 7. PubMed PMID: 21133831. 3: Friedman BW, Hochberg M, Esses D, Bijur PE, Corbo J, Paternoster J, Solorzano C, Toosi B, Lipton RB, Gallagher EJ. A clinical trial of trimethobenzamide/diphenhydramine versus sumatriptan for acute migraines. Headache. 2006 Jun;46(6):934-41. PubMed PMID: 16732839. 4: Ahlskog JE. Trimethobenzamide in elderly patients. Mayo Clin Proc. 2004 Jun;79(6):829. PubMed PMID: 15182103. 5: Katzir H, Mendoza D, Mathern GW. Effect of theophylline and trimethobenzamide when given during kainate-induced status epilepticus: an improved histopathologic rat model of human hippocampal sclerosis. Epilepsia. 2000 Nov;41(11):1390-9. PubMed PMID: 11077452. 6: Colbert DL. Possible explanation for trimethobenzamide cross-reaction in immunoassays of amphetamine/methamphetamine. Clin Chem. 1994 Jun;40(6):948-9. PubMed PMID: 8087994. 7: Jones R, Klette K, Kuhlman JJ, Levine B, Smith ML, Watson CV, Selavka CM. Trimethobenzamide cross-reacts in immunoassays of amphetamine/methamphetamine. Clin Chem. 1993 Apr;39(4):699-700. PubMed PMID: 8472376. 8: Kennett GA, Curzon G. The antiemetic drug trimethobenzamide prevents hypophagia due to acetyl salicylate, but not to 5-HT1B or 5-HT1C agonists. Psychopharmacology (Berl). 1988;96(1):101-3. PubMed PMID: 3147468. 9: Naviasky H. Ion-pair column chromatographic determination of trimethobenzamide hydrochloride in capsule and injection dosage forms: collaborative study. J Assoc Off Anal Chem. 1985 Sep-Oct;68(5):1055-7. PubMed PMID: 4055625. 10: Naviasky H. Quantitative analysis of trimethobenzamide hydrochloride by ion-pair column chromatography and semiquantitative analysis of 3,4,5-trimethoxybenzoic acid by thin-layer chromatography. J Pharm Sci. 1984 Apr;73(4):542-5. PubMed PMID: 6726641. 11: Robert TA, Daigneault EA, Hinton P, Hagardorn AN. The relationship between serum and saliva trimethobenzamide concentrations in man. J Clin Pharmacol. 1982 Jan;22(1):53-8. PubMed PMID: 7061726. 12: Robert TA, Hagardorn AN, Daigneault EA, Brown RD. Analysis of trimethobenzamide in human saliva by gas chromatography--mass spectrometry. J Chromatogr. 1981 Jun 12;224(1):116-21. PubMed PMID: 7263808. 13: Hurley JD, Eshelman FN. Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy. J Clin Pharmacol. 1980 May-Jun;20(5-6 Pt 1):352-6. PubMed PMID: 7400373. 14: Ginsburg CM, Clahsen J. Evaluation of trimethobenzamide hydrochloride (Tigan) suppositories for treatment of nausea and vomiting in children. J Pediatr. 1980 Apr;96(4):767-9. PubMed PMID: 7359291. 15: Holmes C, Flaherty RJ. Trimethobenzamide HCL (Tigan)-induced extrapyramidal dysfunction in a neonate. J Pediatr. 1976 Oct;89(4):669-70. PubMed PMID: 957017. 16: Medoff J. A double-blind evaluation of the anti-emetic efficacy of benzquinamide, prochlorperazine and trimethobenzamide in office practice. Curr Ther Res Clin Exp. 1970 Nov;12(11):706-10. PubMed PMID: 4993123. 17: Tibbs RC. A clinical comparison of rectal pyrilamine maleate and trimethobenzamide hydrochloride for the control of vomiting in children. J Miss State Med Assoc. 1969 Apr;10(4):130-2. PubMed PMID: 4390081. 18: Dobkin AB, Evers W, Israel JS. Double-blind evaluation of metoclopramide (MK 745, Sinemet), trimethobenzamide (Tigan), and a placebo as postanaesthetic anti-emetics following methoxyflurane anaesthesia. Can Anaesth Soc J. 1968 Jan;15(1):80-91. PubMed PMID: 4951153. 19: Borda I, Jick H. Hepatitis following the administration of trimethobenzamide hydrochloride. Arch Intern Med. 1967 Sep;120(3):371-3. PubMed PMID: 6038296. 20: Snow JC. Trimethobenzamide as an antiemetic in surgery for detached retina. Am J Ophthalmol. 1967 Jul;64(1):149-52. PubMed PMID: 6028626.