| Identification | More | [Name]
Maprotiline | [CAS]
10262-69-8 | [Synonyms]
MAPROTILINE
n-methyl-9,10-ethanoanthracene-9(10h)-propanamine
276-Ba
3-(9,10-Dihydro-9,10-ethanoanthracen-9-yl)propylmethylamine
9,10-Ethanoanthracene-9(10H)-propanamine, N-methyl-
9,10-Ethanoanthracene-9(10H)-propylamine, N-methyl-
Ludiomil
maprotylina
n-methyl-10-ethanoanthracene-9(10h)-propylamine
N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine
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 | [EINECS(EC#)]
233-599-4 | [Molecular Formula]
C20H23N | [MDL Number]
MFCD00661057 | [Molecular Weight]
277.4 | [MOL File]
10262-69-8.mol |
| Hazard Information | Back Directory | [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].
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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