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Maprotiline

Basic information Safety Supplier Related

Maprotiline Basic information

Product Name:
Maprotiline
Synonyms:
  • MAPROTILINE
  • n-methyl-9,10-ethanoanthracene-9(10h)-propanamine
  • Maprotiline (base and/or unspecified salts)
  • 9,10-Ethano-9,10-dihydro-9-(3-methylaminopropyl)anthracene
  • Maprotyline
  • N-Methyl-9,10-ethanoanthracene-9(10H)-propan-1-amine
  • 276-Ba
  • 3-(9,10-Dihydro-9,10-ethanoanthracen-9-yl)propylmethylamine
CAS:
10262-69-8
MF:
C20H23N
MW:
277.4
EINECS:
233-599-4
Mol File:
10262-69-8.mol
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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)
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Safety Information

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

Uses

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.

Maprotiline Preparation Products And Raw materials

Raw materials

MaprotilineSupplier

LGM Pharma
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