Maprotiline Hydrochloride

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Cat Number

API0232194

CAS Number

10347-81-6

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Product Detail Description Scientific Support Customer Q&A

CAS Number

10347-81-6

EINECS

233-758-8

Storage

Store at room temperature

Synonyms

Maprotiline Hcl; Ludiomil; 9-(gamma-Methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene hydrochloride; DTXSID2044507; 7C8J54PVFI; NSC-757085

Molecular Formula

C20H24ClN

Molecular Weight

313.9

Smiles

CNCCCC12CCC(C3=CC=CC=C31)C4=CC=CC=C24.Cl

Appearance

White to almost white powder to crystal

Melting Point

240.0-244.0°C

General Description

Maprotiline hydrochloride is a tetracyclic antidepressant belonging to the dibenzobicyclo[2.2.2]octadiene class, structurally distinct from tricyclic antidepressants. Its structure features a tetracyclic ring system with a dimethylaminopropyl side chain. The hydrochloride salt provides water solubility, and maprotiline is a white crystalline powder with a molecular weight of 313.9 Da (as the hydrochloride).

Mechanism of Action

Maprotiline acts primarily as a selective norepinephrine reuptake inhibitor (NRI), blocking the reuptake of norepinephrine at the presynaptic membrane with high affinity, and to a lesser extent, serotonin. It has no significant effect on dopamine reuptake. The drug also has weak histamine H1 and muscarinic receptor blocking properties, contributing to its sedative and anticholinergic effects.

Application

Maprotiline is indicated for the treatment of major depressive disorder, particularly in patients with endogenous depression, psychomotor retardation, or anergic states. It is also used for anxiety disorders and chronic pain syndromes. Its anticholinergic effects are less than those of amitriptyline, but it has a greater risk of seizures than other antidepressants due to its high affinity for the norepinephrine transporter.

In acetic acid-induced colitis in normal and reserpinised depressed rats, maprotiline (10–40 mg/kg, i.p., 4 days) significantly improved macroscopic, histologic, and biochemical (myeloperoxidase) parameters. Reserpine exacerbated colonic damage. The anti-inflammatory effects are likely mediated through the brain-gut axis and direct anti-inflammatory activity.

Fig. 1 Effect of maprotiline (10, 20, and 40 mg/kg, i.p.) on weight of distal colon. (Minaiyan M, et al., 2014)

References

Minaiyan M, et al. Beneficial Effects of Maprotiline in a Murine Model of Colitis in Normal and Reserpinised Depressed Rats. Int Sch Res Notices. 2014;2014:359841.

Does Maprotiline Hydrochloride require protection from light during storage?

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

What is the recommended storage temperature for Maprotiline Hydrochloride?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which accelerates oxidation of the anthracene ring.

Is Maprotiline Hydrochloride stable in tablet formulations with standard excipients?

Yes, when formulated with standard excipients and protected from moisture.

How is the impurity maprotiline N-oxide (an oxidative degradation product) monitored?

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