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Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression.[5] It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary amine.[5] In terms of its chemistry and pharmacology, maprotiline is closely related to such-other secondary-amine TCAs as nortriptyline and protriptyline and has similar effects to them,[6][5] albeit with more distinct anxiolytic effects.[7][8][9] Additionally, whereas protriptyline tends to be somewhat more stimulating and in any case is distinctly more-or-less non-sedating,[10] mild degrees of sedation may be experienced with maprotiline.[11]

Medical uses

Maprotiline is used in the treatment of depression, such as depression associated with agitation or anxiety and has similar efficacy to the antidepressant drug moclobemide.[12] This finding has also been validated by a group of general practitioners who compared the respective efficacy and tolerability of maprotiline and moclobemide.[13]

The use of maprotiline in the treatment of enuresis in pediatric patients has so far not been systematically explored and its use is not recommended.[15] Safety and effectiveness in the pediatric population in general have not been established. Anyone considering the use of maprotiline in a child or adolescent must balance the potential risks with the clinical need.

A very small body of research has also explored the potential of maprotiline in treating diabetic kidney disease[16] and it has been measured against amitriptyline in this regard.[17]

Maprotiline and fluoxetine have also been found, among certain lines of research, to have quite potent anti-profilerative effects against certain forms of cancer of the Burkitt lymphoma type.[18][19] One study also bore ought a certain level of evidence regarding maprotiline’s ability to suppress both cholesterol biosynthesis and hepatocellular carcinoma liver-cancer progression.

Maprotiline was also measured against imipramine, fluoxetine and ketamine in an experiment-model involving two different kinds of chicken differently-conditioned against stress, including (black) Australorps in the proposed treatment of treatment-resistant depression in humans.[20]

In general, lower dosages are recommended for patients over 60 years of age. Dosages of 50 mg to 75 mg daily are usually satisfactory as maintenance therapy for elderly patients who do not tolerate higher amounts.[21][22] In any case, 225 m.g./d. is the absolute-maximum highest recommended dose for this drug, as any more can predispose more significantly to seizures. 150 m.g. is the average optimal daily dose for otherwise-healthy patients who can tolerate a full dose.

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CAS 10262-69-8 Maprotiline | Products & Prices & Suppliers

    • Maprotiline, with the chemical formula C20H23N, has the CAS number 10262-69-8. It is a tetracyclic antidepressant belonging to the class of dibenzazepines. It appears as a white to off-white crystalline powder with a faint odor. Its basic structure consists of four rings attached to a central nitrogen atom. This compound is practically insoluble in water. Maprotiline may cause irritation to the skin and eyes. It is also harmful if swallowed or inhaled. The primary hazard is the potential for adverse effects on the central nervous system. Proper precautions should be taken to avoid exposure to this chemical.Applicable Fields

      Antidepressant: Maprotiline is primarily used as an antidepressant medication. Its purpose in this field involves its ability to inhibit the reuptake of norepinephrine, a neurotransmitter involved in mood regulation. The mechanism of action in antidepressant therapy is the increase in norepinephrine levels, which helps alleviate symptoms of depression.

      Anxiety Disorders: Maprotiline has also been used in the treatment of anxiety disorders. Its mechanism of action in this context is similar to its antidepressant effects, as it increases norepinephrine levels, which can help reduce anxiety symptoms.

      Storage

      Conditions: Store in a cool and dry place.

 

Maprotiline

PharmacologyNeurotransmitter TransportersReceptor Binding

⚠ Attention: For research use only. Not for human or veterinary use.
Molecular FormulaC20H23N
Molecular Weight277.4 g/mol
CAS No.10262-69-8
Cat. No.B082187
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Technical Parameters

Basic Identity
Product Name Maprotiline
CAS 10262-69-8
Synonyms
Molecular Formula C20H23N
Molecular Weight 277.4 g/mol
Structural Identifiers
SMILES CNCCCC12CCC(C3=CC=CC=C31)C4=CC=CC=C24
InChI InChI=1S/C20H23N/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20/h2-5,7-10,15,21H,6,11-14H2,1H3
InChIKey QSLMDECMDJKHMQ-UHFFFAOYSA-N
Commercial & Availability
Standard Pack Sizes 25 mg / 50 mg / 100 mg / Bulk Custom
Availability In Stock
Custom Synthesis Available on request
Handling Information
Solubility 38.6 [ug/mL] (The mean of the results at pH 7.4)
Slightly soluble
1.50e-04 g/L

Structure & Identifiers

Maprotiline Product Overview & Technical Selection

Maprotiline is a tetracyclic antidepressant (TeCA) that functions as a highly selective inhibitor of the norepinephrine transporter (NET). While structurally and mechanistically related to the tricyclic antidepressants (TCAs), maprotiline exhibits a markedly distinct pharmacological profile characterized by high affinity for NET (Ki = 1.8 nM) with minimal interference with serotonin (5-HT) reuptake systems [1]. This compound is primarily utilized in research models of noradrenergic signaling, major depressive disorder, neuropathic pain, and certain cancer pathways, with recent studies also exploring its antiproliferative and neuroprotective properties .

Noradrenergic signaling probe with reported NET selectivity
Supports depression, neuropathic pain, and cancer pathway models
Cell-proliferation and neuroprotection assay context available
Tetracyclic scaffold distinct from tricyclic antidepressants

Why Maprotiline Analogs Compromise Research Reproducibility

Although maprotiline is often grouped with TCAs or other tetracyclic antidepressants, direct substitution with analogs such as amitriptyline, nortriptyline, or mirtazapine is scientifically unsound. Maprotiline possesses a unique bridged tetracyclic structure that confers a distinct selectivity ratio for NET over the serotonin transporter (SERT) [1]. This structural uniqueness translates into a differential side-effect and toxicity profile, most notably an increased risk of seizures in overdose compared to TCAs, and a distinct pattern of GIRK channel modulation [2]. Furthermore, while mirtazapine is also a tetracyclic, its primary mechanism is presynaptic alpha-2 adrenoreceptor antagonism, a pathway completely distinct from maprotiline’s NET inhibition, rendering them non-interchangeable for targeted pathway studies [3].

Maprotiline
Selective NET inhibition; minimal SERT activity
Amitriptyline / Imipramine
Dual NET/SERT inhibition; confounding serotonergic effects in noradrenergic readouts
Maprotiline
GIRK channel EC50 ~47 µM; distinct modulatory profile
Amitriptyline / Nortriptyline
GIRK potency and efficacy may shift; off-target interpretation may differ
Maprotiline
NET inhibition mechanism
Mirtazapine
Alpha-2 adrenoreceptor antagonism; not interchangeable for noradrenergic reuptake studies

Quantitative Evidence for Maprotiline Selection

NET Binding Affinity & Selectivity vs. Tricyclic Antidepressants

Maprotiline demonstrates high-affinity binding to the norepinephrine transporter (NET) with a Ki value of 1.8 nM, as measured in radioligand binding assays . It is a highly selective noradrenergic reuptake inhibitor, exhibiting minimal to no affinity for the serotonin transporter (SERT), in direct contrast to many tricyclic antidepressants like amitriptyline and imipramine which potently inhibit both NET and SERT [1]. This selective profile is a direct consequence of its tetracyclic structure.

NET binding & selectivity
Head-to-head
Ki = 1.8 nM (NET); negligible SERT inhibition
vs. Amitriptyline Ki NET ~14-35 nM, SERT ~4 nM
Supports noradrenergic-specific pathway studies without serotonergic confound
PharmacologyNeurotransmitter TransportersReceptor BindingAntidepressant Selectivity

GIRK Channel Modulation vs. Amitriptyline & Nortriptyline

In functional studies on G-protein-coupled inwardly rectifying potassium (GIRK) channels, maprotiline exhibits a distinct inhibitory profile compared to structurally related TCAs. This channel modulation is a known off-target effect of many antidepressants. The EC50 for inhibition of GIRK1/2 channels was measured at 47.1 ± 10.1 µM for maprotiline, which is significantly different from the values observed for amitriptyline (22.3 ± 2.8 µM) and nortriptyline (50.5 ± 12.8 µM) [1].

GIRK channel modulation
Head-to-head
EC50 = 47.1 ± 10.1 µM (GIRK1/2)
Amitriptyline: 22.3 ± 2.8 µM; Nortriptyline: 50.5 ± 12.8 µM
Distinct ion channel inhibition profile for off-target research
NeurophysiologyIon Channel PharmacologyAntidepressant MechanismsGIRK Channel

Comparative Seizure Risk in Overdose vs. Tricyclic Antidepressants

A retrospective review of 1,313 cases of cyclic antidepressant exposures reported to a poison center quantified a significant difference in seizure incidence. Seizures were documented in 12.2% of maprotiline exposures, compared to a 3.0% incidence in the tricyclic antidepressant (TCA) group (P < 0.01). The incidence was highest for amoxapine at 24.5%, while trazodone showed 0% [1]. Despite the higher seizure risk, maprotiline overdose was associated with less severe peripheral autonomic and cardiac toxicity than typical TCA overdoses [2].

 

Clinical Efficacy & Tolerability vs. SSRI Paroxetine

A large double-blind, randomized, multicenter study (n=544 outpatients) directly compared the therapeutic benefits of dose escalation for maprotiline (100 mg/day) versus the SSRI paroxetine (20 mg/day) in patients with inadequate treatment response. While both drugs showed comparable antidepressant efficacy, the side-effect profiles were distinct. The maprotiline group exhibited a higher frequency of anticholinergic side effects, whereas the paroxetine group reported more nausea, sweating, and headache [1]. This study provides a quantified benchmark for the clinical performance and side-effect burden of maprotiline relative to a major modern antidepressant class.

Efficacy vs SSRI
Head-to-head
Comparable antidepressant efficacy (p > 0.05) to paroxetine 20 mg/day
6-week RCT; n=544; maprotiline 100 mg/day; distinct tolerability profile
Supports noradrenergic comparator to SSRI in trial design; anticholinergic side-effect context noted
Clinical PsychopharmacologyDepression ResearchComparative EfficacyAntidepressant Dosing

Validated Research & Industrial Applications of Maprotiline

Noradrenergic Signaling in Depression & Anxiety Models

Given its validated high selectivity for the norepinephrine transporter (NET) over the serotonin transporter (SERT) [1], maprotiline is the compound of choice for in vivo and in vitro studies aiming to isolate and characterize the behavioral and molecular consequences of enhanced noradrenergic tone. Unlike the tricyclic amitriptyline, which has a dual mechanism, maprotiline allows researchers to attribute observed effects—such as changes in beta-adrenergic receptor sensitivity or cAMP signaling [2]—specifically to norepinephrine reuptake inhibition.

Comparative Toxicology & Overdose Model Research

Due to its well-documented, quantitatively distinct toxicity profile—specifically a 4.1-fold higher risk of seizures in overdose compared to classic TCAs [3]—maprotiline is a valuable tool compound in toxicology. It serves as a positive control or comparative agent in studies modeling antidepressant-induced seizures, cardiotoxicity, and the development of novel overdose countermeasures, where its unique pattern of high CNS excitability with relatively low cardiotoxicity is essential for mechanistic dissection [4].

GIRK Channel & Ion Channel Pharmacology Studies

The quantified differential inhibitory effect of maprotiline on GIRK1/2 channels (EC50 = 47.1 µM), which is distinct from that of amitriptyline (EC50 = 22.3 µM) and nortriptyline (EC50 = 50.5 µM) [5], positions this compound as a critical tool for probing structure-activity relationships (SAR) around potassium channel modulation by antidepressants. Researchers investigating the molecular determinants of GIRK channel block can utilize maprotiline as a structurally unique comparator to TCAs.

Quality Control & Stability Testing of Pharmaceutical Formulations

The development and validation of specific, stability-indicating HPLC methods for the determination of maprotiline and its related impurities in solid dosage forms provide a technical framework for analytical chemists in pharmaceutical quality control [6]. This established methodology, capable of resolving maprotiline from its degradation products and synthetic impurities, is directly applicable for batch release, stability studies, and method development for related tetracyclic compounds.

Application
Selection Property
Validation Focus
Noradrenergic signaling studies
Reported NET selectivity over SERT
β-adrenergic sensitivity, cAMP pathway endpoints
Overdose toxicology models
Differential seizure incidence profile
CNS excitability vs. cardiotoxicity endpoints
Ion channel pharmacology
GIRK channel modulation (EC50 context)
Structure-activity relationship around potassium channel block
Analytical quality control
Stability-indicating HPLC method
Impurity resolution, batch release, stability studies

Technical Documentation Hub

Structured technical reading across foundational, methodological, troubleshooting, and validation/comparative pathways. Use the hub when you need more detail before procurement.

55 linked technical documents

Explore Hub

FoundationalNovember 2025

The Core Mechanism of Maprotiline on Norepinephrine Transporters: An In-depth Technical Guide

FoundationalNovember 2025

tetracyclic antidepressant maprotiline neurochemical effects

FoundationalNovember 2025

The Tetracyclic Antidepressant Maprotiline: An In-depth Technical Guide to its Effects on Central Adrenergic Synapses

View all 55 documents
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Product Requirements

Maprotiline

Maprotiline Structure

Maprotiline structure

CAS No.
10262-69-8
Chemical Name:
Maprotiline
Synonyms
276-Ba;Ludiomil;MAPROTILINE;Maprotyline;maprotylina;Maprotiline USP/EP/BP;Maprotiline (base and/or unspecified salts);n-methyl-10-ethanoanthracene-9(10h)-propylamine;n-methyl-9,10-ethanoanthracene-9(10h)-propanamine;N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine
CBNumber:
CB6149440
Molecular Formula:
C20H23N
Molecular Weight:
277.4
MDL Number:
MFCD00661057
MOL File:
10262-69-8.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-04-21 10:31:43
Product description Number Pack Size Price
Maprotiline ≥98% AA0007VG 50mg $120
Maprotiline ≥98% AA0007VG 250mg $380
Maprotiline ≥98% AA0007VG 1g $1060
Maprotiline M188003 250mg $575
MAPROTILINE 95.00% API0000638 100MG $525
Request For Quotation

Maprotiline Properties

Melting point 92-94°
Boiling point 410.26°C (rough estimate)
Density 0.9801 (rough estimate)
refractive index 1.4900 (estimate)
pka pKa 10.5±0.2(H2O t=25.0) (Uncertain)
Water Solubility 833.4ug/L(22.5 ºC)
CAS DataBase Reference 10262-69-8(CAS DataBase Reference)
EWG’s Food Scores 1
FDA UNII 2U1W68TROF
NCI Drug Dictionary Ludiomil
ATC code N06AA21
NIST Chemistry Reference Maprotiline(10262-69-8)

 

SAFETY

Risk and Safety Statements

RIDADR 3249
HazardClass 6.1(b)
PackingGroup III
Toxicity LD50 oral in rat: 760mg/kg

Maprotiline price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
aablocks AA0007VG Maprotiline ≥98% 10262-69-8 50mg $120 2026-05-25 Buy
aablocks AA0007VG Maprotiline ≥98% 10262-69-8 250mg $380 2026-05-25 Buy
aablocks AA0007VG Maprotiline ≥98% 10262-69-8 1g $1060 2026-05-25 Buy
TRC M188003 Maprotiline 10262-69-8 250mg $575 2021-12-16 Buy
American Custom Chemicals Corporation API0000638 MAPROTILINE 95.00% 10262-69-8 100MG $525 2021-12-16 Buy

Maprotiline Chemical Properties, Uses, Production

Originator

Maprotiline hydrochloride ,Mylan

Uses

Antidepressant.

Uses

Maprotiline disrupts neuronal reuptake of monoamines in the CNS and possesses moderate tranquilizing and cholinergic activity. It improves mood significantly and relieves feelings of fear. Maprotiline is used in various forms of depression accompanied by a feeling of fear and irritability.

Definition

ChEBI: Maprotiline is a member of anthracenes.

Manufacturing Process

9-(3-Hydroxypropyl)anthracene was prepared by reduction of 3-(9-anthryl) propionic acid with LiAlH4. By action of thionylchloride and then methylamine the 9-(3-hydroxypropyl)anthracene was converted to 9-(3-methylaminopropyl) anthracene. By addition of ethylene to 9-(3-methylaminopropyl)anthracene (at 150°C, a pressure of ethylene 50 atm, 24 hours) was obtained 3-(9,10- dihydro-9,10-ethanoanthracene-9-yl)-N-methylpropylamine. Hydrochloride 3- (9,10-dihydro-9,10-ethanoanthracene-9-yl)-N-methylpropylamine may be prepared by action hydrochloric acid.

Therapeutic Function

Antidepressant

Mechanism of action

Maprotiline is slowly but completely absorbed from the GI tract, and like the other TCAs, it is metabolized by the polymorphic CYP2D6 and CYP2C19 isoforms in the liver, primarily to pharmacologically active N-desmethylmaprotiline and to maprotiline-N-oxide.Maprotiline is distributed into breast milk at concentrations similar to those found at steady state in maternal blood. The elimination half-life of maprotiline averages 43 hours (60–90 hours for its N-desmethyl metabolite).Maprotiline shares the toxic potentials of the TCAs, and the usual precautions of TCA administration should be observed.

Clinical Use

Maprotiline is a secondary amine dibenzobicyclooctadiene (a tetracyclic antidepressant) that differs structurally from the TCAs by having an ethylene bridge in its central ring, resulting in a rigid bicyclomolecular skeleton .
Maprotiline exhibits the highest affinity and selectivity for the NE transporter. Its antidepressant mechanism of action is similar to that of desipramine, with an onset of action of up to 2 to 3 weeks.

Side effects

Although most of the TCAs have been reported to induce seizures, it is generally recognized that maprotiline may be associated with a higher incidence of dose-dependent seizures compared with the other secondary TCAs. Maprotiline has been reported to produce sedation in depressed patients and to reduce aggressive behavior in animals. Maprotiline also shares the anticholinergic and cardiovascular effects of the secondary TCAs and may cause electrocardiographic changes, tachycardia, and postural hypotension.

Synthesis

Maprotiline, N-methyl-9,10-ethanoanthracen-9(10H)-propylamine (7.1.22), is synthesized by a 42 cycloaddition reaction of 9-(3-methylaminopropyl)anthracene with ethylene [39¨C41].

Synthesis_10262-69-8

Maprotiline is frequently referred to as a tetracyclic antidepressant. This °hybrid± drug, containing both elements of °classic tricyclic antidepressants± and protriptyline elements, is pharmacologically and clinically more similar to imipramine.

Maprotiline synthesis

90-44-8
10262-69-8
Synthesis of Maprotiline from Anthrone

 

  • Product Name: Maprotiline
  • Molecular Weight: 277.411
  • Molecular Formula: C20H23N
  • Synonyms: [14C]-Maprotiline; 276-Ba; 3-(9,10-Dihydro-9,10-ethanoanthracen-9-yl)-N-methylpropan-1-amine; 3-(9,10-Dihydro-9,10-ethanoanthracen-9-yl)propylmethylamine; 9,10-Ethano-9,10-dihydro-9-(3-methylaminopropyl)anthracene; 9-[3-(methylamino)propyl]-9,10-dihydro-9,10-ethanoanthracene;

Available forms

  • Coated tablets: 10 mg, 25 mg, 50 mg, and 75 mg
  • Injectable concentrate, 25 mg

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