Maprotiline
- Product Name
- Maprotiline
- 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
- Formula Weight
- 277.4
- MOL File
- 10262-69-8.mol
Maprotiline Property
- 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
- RIDADR
- 3249
- HazardClass
- 6.1(b)
- PackingGroup
- III
- Toxicity
- LD50 oral in rat: 760mg/kg
N-Bromosuccinimide Price
- Product number
- M188003
- Product name
- Maprotiline
- Packaging
- 250mg
- Price
- $575
- Updated
- 2021/12/16
- Product number
- API0000638
- Product name
- MAPROTILINE
- Purity
- 95.00%
- Packaging
- 100MG
- Price
- $525
- Updated
- 2021/12/16
Maprotiline Chemical Properties,Usage,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].
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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