Maprotiline

Base Information

• Chemical Name: Maprotiline
• CAS No.: 10262-69-8
• Molecular Formula: C20H23N
• Molecular Weight: 277.409
• Hs Code.: 2921499090
• European Community (EC) Number: 233-599-4
• UNII: 2U1W68TROF
• DSSTox Substance ID: DTXSID7045029
• Nikkaji Number: J9.818C
• Wikipedia: Maprotiline
• Wikidata: Q418361
• NCI Thesaurus Code: C61824
• Pharos Ligand ID: GG92NA7HQ191
• Metabolomics Workbench ID: 43196
• ChEMBL ID: CHEMBL21731,CHEMBL1201257
• Mol file: 10262-69-8.mol

Synonyms:Ba-34,276;Ba34,276;Deprilept;Dibencycladine;Hydrochloride, Maprotiline;Ludiomil;Maprolu;Maprotilin;Maprotilin Holsten;Maprotilin neuraxpharm;Maprotilin ratiopharm;Maprotilin TEVA;maprotilin von ct;Maprotilin-neuraxpharm;Maprotilin-ratiopharm;Maprotilin-TEVA;Maprotiline;Maprotiline Hydrochloride;Maprotiline Mesylate;Mesylate, Maprotiline;Mirpan;N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine;Novo Maprotiline;Novo-Maprotiline;Psymion

Chemical Property of Maprotiline

Chemical Property:

• Vapor Pressure: 1.35E-06mmHg at 25°C
• Melting Point: 92-94°
• Refractive Index: 1.599
• Boiling Point: 399.615 °C at 760 mmHg
• PKA: pKa 10.5±0.2(H2O t=25.0) (Uncertain)
• Flash Point: 187.657 °C
• PSA: 12.03000
• Density: 1.081 g/cm³
• LogP: 4.60230
• Water Solubility.: 833.4ug/L(22.5 oC)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 277.183049738
• Heavy Atom Count: 21
• Complexity: 339

Purity/Quality:

98%,99%, ^*data from raw suppliers

Maprotiline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCCC12CCC(C3=CC=CC=C31)C4=CC=CC=C24
• Recent ClinicalTrials: Pharmacovigilance in Gerontopsychiatric Patients
• Recent EU Clinical Trials: Pharmacovigilance in children and adolescents:
• 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. Antidepressant.
• Therapeutic Function: Antidepressant
• 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.

Technology Process of Maprotiline

There total 7 articles about Maprotiline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-bicyclo<2.2.2>octadienyl-(1)>-propionsaeure-methylamid (23716-34-9) → maprotiline (10262-69-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1002/hlca.19690520602

Reference yield:

anthracen-9(10H)-one (90-44-8) → maprotiline (10262-69-8)

Guidance literature:

Multi-step reaction with 6 steps

1: (i) KOtBu, tBuOH, (ii) aq. HCl

2: Zn, aq. NH₃

3: dimethylformamide / 170 °C

4: (COCl)2

6: LiAlH₄ / diethyl ether

With ammonium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; zinc; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19690520602

Reference yield:

3-bicyclo<2.2.2>octadienyl-(1)>-propionsaeure (6812-49-3) → maprotiline (10262-69-8)

Guidance literature:

Multi-step reaction with 3 steps

1: (COCl)2

3: LiAlH₄ / diethyl ether

With lithium aluminium tetrahydride; oxalyl dichloride; In diethyl ether;

DOI:10.1002/hlca.19690520602

upstream raw materials:

3-bicyclo<2.2.2>octadienyl-(1)>-propionsaeure-methylamid

anthracen-9(10H)-one

3-bicyclo<2.2.2>octadienyl-(1)>-propionsaeure

3-anthracen-9-ylpropionic acid

Downstream raw materials:

C₃₅H₄₄N₂O

5-Methyl-2--1,4-benzochinon

6-Methyl-2--1,4-benzochinon

Refernces

• 1、 Wilhelm,Schmidt. "Synthesis and properties of 1-aminoalkyl-dibenzo(b,e)bicyclo(2,2,2) octadienes". . p. 1385 - 1395. Retrieved 2007/10/05.