Metoclopramide Hydrochloride

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Cat Number

API54143576

CAS Number

7232-21-5

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CAS Number

7232-21-5

EINECS

230-634-5

Storage

Store at room temperature

Synonyms

Maxolon; metoclopramide hcl monohydrate; Metoclopramide hydrochloride monohydrate; metipamid; AHR-3070-C; Gastromax; Metramid; Mygdalon; Paspertin

Molecular Formula

C14H25Cl2N3O3

Molecular Weight

354.3

Smiles

CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Cl.O.Cl

Appearance

White or practically white, crystalline powder

Melting Point

171-173°C

General Description

Metoclopramide hydrochloride is a substituted benzamide with a para‑amino group and a chloro substituent, structurally related to procainamide. Its chemical structure is 4‑amino‑5‑chloro‑N‑[2‑(diethylamino)ethyl]‑2‑methoxybenzamide hydrochloride. Metoclopramide is a white crystalline powder that is readily soluble in water. It is a dopamine D2 receptor antagonist and a 5‑HT4 receptor agonist.

Mechanism of Action

Metoclopramide acts as a dopamine D2 receptor antagonist in the chemoreceptor trigger zone (CTZ), providing antiemetic effects, and as a 5‑HT4 receptor agonist in the gastrointestinal tract, enhancing acetylcholine release and stimulating motility. It increases lower esophageal sphincter tone, accelerates gastric emptying, and coordinates antral and duodenal contractions. The drug also has weak 5‑HT3 receptor antagonism.

Application

Metoclopramide is indicated for the treatment of nausea and vomiting associated with chemotherapy, radiation, and postoperative states, and for diabetic gastroparesis. It is also used for the treatment of gastroesophageal reflux disease (GERD).

PET imaging with [¹¹C]metoclopramide in mice showed that cation transporter inhibitors (cimetidine, sulpiride) and unlabeled metoclopramide decreased kidney/liver uptake (~2.5-fold), inhibited metabolism, and reduced urinary excretion, increasing plasma concentrations. Slc22a1/2 knockout reduced kidney/liver uptake ~1.3-fold. OCT1/2 contribute to uptake and MATEs to urinary excretion of metoclopramide. Transporter variability may contribute to pharmacokinetic variability and side effects.

Fig. 1 Mean time-radioactivity curves. (Hernández-Lozano I, et al., 2021)

References

Hernández-Lozano I, et al. Influence of Cation Transporters (OCTs and MATEs) on the Renal and Hepatobiliary Disposition of [11C]Metoclopramide in Mice. Pharm Res. 2021;38(1):127-140.

Metoclopramide (MCP), a D2R antagonist, inhibited dengue virus infection in D2R‑expressing Neuro‑2a cells but not in D2R‑negative BHK‑21 cells. MCP blocked DENV binding, reduced dsRNA replication, and prevented neuronal cytotoxicity in vitro. In vivo, MCP protected against DENV‑induced CNS neuropathy and mortality. Repurposing MCP as an anti‑dengue therapeutic is promising.

Fig. 2 Metoclopramide (MCP) treatment delays the clinical scores in suckling mice during dengue virus (DENV) infection. (Shen TJ, et al., 2021)

References

Shen TJ, et al. Repurposing the Antiemetic Metoclopramide as an Antiviral Against Dengue Virus Infection in Neuronal Cells. Front Cell Infect Microbiol. 2021;10:606743.

Does Metoclopramide Hydrochloride require protection from light during storage?

Yes, it is photosensitive. Light exposure can cause discoloration and degradation of the benzamide ring. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Metoclopramide Hydrochloride?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which accelerate hydrolysis of the amide bond and oxidation.

Is Metoclopramide Hydrochloride stable in injectable and oral solution formulations?

Aqueous solutions are stable when protected from light and stored at room temperature.

How is the impurity 4-amino-5-chloro-2-methoxybenzoic acid (a hydrolysis product) monitored?

This degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains below pharmacopoeial limits.