Metoclopramide HCl | CAS# 54143-57-6 | Antiemetic agent

MedKoo Cat#: 573503 | Name: Metoclopramide HCl

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Description:

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

Metoclopramide HCl is a dopamine D2 antagonist. It is also an antiemetic agent.

Chemical Structure

Metoclopramide HCl

CAS#7232-21-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 573503

Name: Metoclopramide HCl

CAS#: 7232-21-5 (HCl)

Chemical Formula: C14H23Cl2N3O2

Exact Mass: 335.1167

Molecular Weight: 336.26

Elemental Analysis: C, 50.01; H, 6.89; Cl, 21.09; N, 12.50; O, 9.52

Price and Availability

Size	Price	Availability	Quantity
10g	USD 350.00	2 Weeks
25g	USD 650.00	2 Weeks

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Related CAS #

7232-21-5 (HCl) 54143-57-6 364-62-5 (free base)

Synonym

AHR-3070-C, Maxolon, Metoclopramide HCl, Metoclopramide hydrochloride; Rimetin;

IUPAC/Chemical Name

4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide hydrochloride

InChi Key

RVFUNJWWXKCWNS-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H22ClN3O2.ClH/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3;/h8-9H,4-7,16H2,1-3H3,(H,17,19);1H

SMILES Code

O=C(NCCN(CC)CC)C1=CC(Cl)=C(N)C=C1OC.[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

Shelf Life

>3 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Metoclopramide HCl (Metoclopramide hydrochloride) is a selective dopamine D2 receptor antagonist.

In vitro activity:

This study aimed at elucidating the effect of metoclopramide on triple-negative breast cancer, MDA-MB-231 cells were treated with various concentrations of metoclopramide, the cell proliferation was detected by MTT method, the apoptosis rate was detected by Annexin V/PI double staining method, the expression change of death-related protein was detected by Western Blot. This study found that metoclopramide inhibits cell proliferation and induces cell apoptosis of MDA-MB-231 in a concentration-dependent manner, and the Bcl family was involved in this process. Reference: Pharmazie. 2021 Apr 1;76(4):172-174. https://pubmed.ncbi.nlm.nih.gov/33849703/

In vivo activity:

The present study evaluated behavioral and neurochemical effects of long-term exposure to MET (methionine) in zebrafish. The results showed that metoclopramide was not only beneficial in improving MET-induced cognitive impairment but it also prevented social withdrawal in zebrafish exposed to MET. In addition, metoclopramide reversed anxiety-like behavior, as indicated by significant changes in locomotion activity. Reference: Zebrafish. 2023 Feb;20(1):19-27. https://pubmed.ncbi.nlm.nih.gov/36577055/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	59.48
	DMSO	20.0	59.48
	Ethanol	43.5	129.37
	PBS (pH 7.2)	10.0	29.74
	Water	67.0	199.25

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 336.26 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.

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

Formulation protocol:

1. Chen Y, Zhang M, Ji X, Zhao J, Qin S, Ji Y, Fan R, Liu Y, Lu P. The anti-cancer effect of metoclopramide on triple-negative breast cancer cells. Pharmazie. 2021 Apr 1;76(4):172-174. doi: 10.1691/ph.2021.0977. PMID: 33849703. 2. Riether C, Radpour R, Kallen NM, Bürgin DT, Bachmann C, Schürch CM, Lüthi U, Arambasic M, Hoppe S, Albers CE, Baerlocher GM, Ochsenbein AF. Metoclopramide treatment blocks CD93-signaling-mediated self-renewal of chronic myeloid leukemia stem cells. Cell Rep. 2021 Jan 26;34(4):108663. doi: 10.1016/j.celrep.2020.108663. PMID: 33503440. 3. Ved H, Doshi G, Bhatia N, Kale P. Metoclopramide as a Potential Antipsychotic Against Long-Term Methionine Exposure in Zebrafish. Zebrafish. 2023 Feb;20(1):19-27. doi: 10.1089/zeb.2022.0033. Epub 2022 Dec 27. PMID: 36577055. 4. Shen TJ, Hanh VT, Nguyen TQ, Jhan MK, Ho MR, Lin CF. Repurposing the Antiemetic Metoclopramide as an Antiviral Against Dengue Virus Infection in Neuronal Cells. Front Cell Infect Microbiol. 2021 Feb 2;10:606743. doi: 10.3389/fcimb.2020.606743. PMID: 33634036; PMCID: PMC7902071.

In vitro protocol:

In vivo protocol:

1. Ved H, Doshi G, Bhatia N, Kale P. Metoclopramide as a Potential Antipsychotic Against Long-Term Methionine Exposure in Zebrafish. Zebrafish. 2023 Feb;20(1):19-27. doi: 10.1089/zeb.2022.0033. Epub 2022 Dec 27. PMID: 36577055. 2. Shen TJ, Hanh VT, Nguyen TQ, Jhan MK, Ho MR, Lin CF. Repurposing the Antiemetic Metoclopramide as an Antiviral Against Dengue Virus Infection in Neuronal Cells. Front Cell Infect Microbiol. 2021 Feb 2;10:606743. doi: 10.3389/fcimb.2020.606743. PMID: 33634036; PMCID: PMC7902071.

1: Storelli F, Anoshchenko O, Unadkat JD. Successful prediction of human brain Kp,uu of P-gp substrates using the proteomics-informed relative expression factor approach. Clin Pharmacol Ther. 2021 Mar 6. doi: 10.1002/cpt.2227. Epub ahead of print. PMID: 33675056. 2: van Gelder MMHJ, Nordeng H. Antiemetic Prescription Fills in Pregnancy: A Drug Utilization Study Among 762,437 Pregnancies in Norway. Clin Epidemiol. 2021 Feb 26;13:161-174. doi: 10.2147/CLEP.S287892. PMID: 33664595; PMCID: PMC7924249. 3: Ho CC, Su YJ. Esophageal Bezoar Successfully Treated by Intravenous Metoclopramide. Am J Med Sci. 2021 Feb 26:S0002-9629(21)00071-9. doi: 10.1016/j.amjms.2021.02.018. Epub ahead of print. PMID: 33647284. 4: Metoclopramide nasal spray (Gimoti) for diabetic gastroparesis. Med Lett Drugs Ther. 2021 Jan 11;63(1615):5-7. PMID: 33646999. 5: Kim K, Jung J, Kim H, Kim JT, Oh JM, Kim H. Potentially Inappropriate Prescriptions to Older Patients in Emergency Departments in South Korea: A Retrospective Study. Ther Clin Risk Manag. 2021 Feb 19;17:173-181. doi: 10.2147/TCRM.S291458. PMID: 33642859; PMCID: PMC7903959. 6: Shen TJ, Hanh VT, Nguyen TQ, Jhan MK, Ho MR, Lin CF. Repurposing the Antiemetic Metoclopramide as an Antiviral Against Dengue Virus Infection in Neuronal Cells. Front Cell Infect Microbiol. 2021 Feb 2;10:606743. doi: 10.3389/fcimb.2020.606743. PMID: 33634036; PMCID: PMC7902071. 7: Hishinuma K, Yamane R, Yokoo I, Arimoto T, Takahashi K, Goto M, Saito Y, Nakajima K, Murashima A, Hayashi M. Pregnancy outcome after first trimester exposure to domperidone-An observational cohort study. J Obstet Gynaecol Res. 2021 Feb 25. doi: 10.1111/jog.14709. Epub ahead of print. PMID: 33631840. 8: Veldhuis P, Melse M, Mullaart N. Implementation of isopropyl alcohol (IPA) inhalation as the first-line treatment for nausea in the emergency department: practical advantages and influence on the quality of care. Int J Emerg Med. 2021 Feb 24;14(1):15. doi: 10.1186/s12245-021-00334-z. PMID: 33627064; PMCID: PMC7905555. 9: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Acupuncture. 2021 Feb 15. PMID: 30000950. 10: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Metoclopramide. 2021 Feb 15. PMID: 30000411. 11: Ristescu AI, Pintilie G, Moscalu M, Rusu D, Grigoras I. Preoperative Cognitive Impairment and the Prevalence of Postoperative Delirium in Elderly Cancer Patients-A Prospective Observational Study. Diagnostics (Basel). 2021 Feb 10;11(2):275. doi: 10.3390/diagnostics11020275. PMID: 33578953; PMCID: PMC7916677. 12: Biskup A, Plagens-Rotman K, Polocka-Molinska M, Merks P. The impact of multimodal therapies on the comfort and safety of patients in the immediate post-anaesthetic period following gynaecological procedures - part I. Ginekol Pol. 2021 Feb 12. doi: 10.5603/GP.a2020.0167. Epub ahead of print. PMID: 33576475. 13: Zhang R, Hristovski D, Schutte D, Kastrin A, Fiszman M, Kilicoglu H. Drug repurposing for COVID-19 via knowledge graph completion. J Biomed Inform. 2021 Feb 8;115:103696. doi: 10.1016/j.jbi.2021.103696. Epub ahead of print. PMID: 33571675; PMCID: PMC7869625. 14: Gnanapandithan K, Karthik N, Gerber J. Methadone, Metoclopramide and Metronidazole Interaction Causing Torsades de Pointes. Clin Pract. 2021 Feb 7;11(1):101-105. doi: 10.3390/clinpract11010015. PMID: 33562182; PMCID: PMC7931031. 15: Rhee SY, Kim HS. Subcortical Structure Disruption in Diffusion Tensor Tractography of the Patient With the Syndrome of Irreversible Lithium- Effectuated Neurotoxicity Combined With Neuroleptic Malignant Syndrome: A Case Report. Clin Neuropharmacol. 2021 Feb 5. doi: 10.1097/WNF.0000000000000439. Epub ahead of print. PMID: 33560007. 16: Hernández-Lozano I, Mairinger S, Sauberer M, Stanek J, Filip T, Wanek T, Ciarimboli G, Tournier N, Langer O. Influence of Cation Transporters (OCTs and MATEs) on the Renal and Hepatobiliary Disposition of [11C]Metoclopramide in Mice. Pharm Res. 2021 Jan;38(1):127-140. doi: 10.1007/s11095-021-03002-2. Epub 2021 Feb 8. PMID: 33559045; PMCID: PMC7902338. 17: Balihar K, Kotyza J, Zdrhova L, Kozeluhova J, Krcma M, Matejovic M. Characterization of esophageal motor activity, gastroesophageal reflux, and evaluation of prokinetic effectiveness in mechanically ventilated critically ill patients: a high-resolution impedance manometry study. Crit Care. 2021 Feb 8;25(1):54. doi: 10.1186/s13054-021-03479-8. PMID: 33557860; PMCID: PMC7870125. 18: Saleh AS, Khokhar T, Nawaz A. 62. Metoclopramide-induced atrial fibrillation: a case report. Eur J Emerg Med. 2020 Sep 1;27(Suppl 1):e12-e13. doi: 10.1097/01.mej.0000697864.53903.b1. PMID: 33555802. 19: Buddam A, Hoilat GJ, Dacha S. Gastric Stasis. 2021 Feb 9. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2021 Jan–. PMID: 29489278. 20: Wolfes J, Ellermann C, Burde S, Fehr M, Eckardt L, Frommeyer G. Proarrhythmic potential of metoclopramide in a sensitive whole-heart model. Basic Clin Pharmacol Toxicol. 2021 Feb 6. doi: 10.1111/bcpt.13567. Epub ahead of print. PMID: 33548156.