Maprotiline Chemical 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)

NIST Chemistry Reference

Maprotiline(10262-69-8)

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

LD50 oral in rat: 760mg/kg

Maprotiline Usage And Synthesis

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 4
2 cycloaddition reaction of 9-(3-methylaminopropyl)anthracene with ethylene [39¨C41].

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.

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