Trimipramine

Base Information

• Chemical Name: Trimipramine
• CAS No.: 739-71-9
• Molecular Formula: C20H26 N2
• Molecular Weight: 294.44
• European Community (EC) Number: 212-008-3
• UNII: QJ9MUH57H8,6S082C9NDT,9K5931C1H5
• DSSTox Substance ID: DTXSID8023715
• Nikkaji Number: J53.921J,J6.960D,J86.105G
• Wikipedia: Trimipramine
• Wikidata: Q423498
• NCI Thesaurus Code: C61990
• RXCUI: 10834
• Pharos Ligand ID: 8L68PDSTTGNY
• Metabolomics Workbench ID: 43032
• ChEMBL ID: CHEMBL644
• Mol file: 739-71-9.mol

Synonyms:10,11 Dihydro-N,N,beta-trimethyl-5H-dibenz(b,f)azepine-5-propanamine;Apo Trimip;Apo-Trimip;ApoTrimip;beta, Trimipramin;Eldoral;Herphonal;Novo Tripramine;Novo-Tripramine;NovoTripramine;Nu Trimipramine;Nu-Trimipramine;NuTrimipramine;Rhotrimine;Stangyl;Surmontil;Surmontil Maleate;Trimeprimine;Trimidura;Trimineurin;Trimineurin Maleate;Trimipramin AZU;Trimipramin beta;Trimipramin neurazpharm;Trimipramin Stada;Trimipramin-neurazpharm;Trimipramine;Trimipramine Maleate;Trimipramine Maleate (1:1);Trimipramine Maleate (1:1), (+)-Isomer;Trimipramine Maleate (1:1), (+-)-Isomer;Trimipramine Maleate (1:1), (-)-Isomer;Trimipramine Mesylate;Trimipramine Monohydrochloride;Trimipramine, (+-)-Isomer;Trimipramine, (-)-Isomer;Trimipraminneurazpharm

Chemical Property of Trimipramine

Chemical Property:

• Melting Point: 45°
• Refractive Index: 1.6450 (estimate)
• Boiling Point: 426.2°C (rough estimate)
• PKA: pKa 8.0 (Uncertain)
• Flash Point: 9℃
• PSA: 6.48000
• Density: 0.9912 (rough estimate)
• LogP: 4.18600
• Storage Temp.: 2-8°C
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 294.209598838
• Heavy Atom Count: 22
• Complexity: 317

Purity/Quality:

99.9% ^*data from raw suppliers

Trimipramine solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CC(CN1C2=CC=CC=C2CCC3=CC=CC=C31)CN(C)C
• Recent ClinicalTrials: Pharmacovigilance in Gerontopsychiatric Patients
• Recent EU Clinical Trials: Pharmacovigilance in children and adolescents:
• Uses: Antidepressant.
• Therapeutic Function: Antidepressant
• Clinical Use: Although trimipramine has the weakest binding affinity for the monoamine transporters, it shares the pharmacological and toxicity actions of the other TCAs and is used primarily in the treatment of depression.
• Drug interactions: Potentially hazardous interactions with other drugs Alcohol: increased sedative effect. Analgesics: increased risk of CNS toxicity with tramadol; possibly increased risk of side effects with nefopam; possibly increased sedative effects with opioids. Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone - avoid; increased risk of ventricular arrhythmias with disopyramide, flecainide or propafenone; avoid with dronedarone. Antibacterials: increased risk of ventricular arrhythmias with delamanid and moxifloxacin and possibly telithromycin - avoid with delamanid and moxifloxacin. Anticoagulants: may alter anticoagulant effect of coumarins. Antidepressants: enhanced CNS excitation and hypertension with MAOIs and moclobemide - avoid; concentration possibly increased with SSRIs; risk of ventricular arrhythmias with citalopram and escitalopram - avoid; possible increased risk of convulsions with vortioxetine. Antiepileptics: convulsive threshold lowered; concentration reduced by carbamazepine, phenobarbital and possibly fosphenytoin, phenytoin and primidone. Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol. Antipsychotics: increased risk of ventricular arrhythmias especially with droperidol, fluphenazine, haloperidol, pimozide, sulpiride and zuclopenthixol - avoid; increased risk of ventricular arrhythmias with risperidone; increased antimuscarinic effects with clozapine and phenothiazines; concentration increased by antipsychotics. Antivirals: increased risk of ventricular arrhythmias with saquinavir - avoid; concentration possibly increased with ritonavir. Atomoxetine: increased risk of ventricular arrhythmias and possibly convulsions. Beta-blockers: increased risk of ventricular arrhythmias with sotalol. Clonidine: tricyclics antagonise hypotensive effect; increased risk of hypertension on clonidine withdrawal. Dapoxetine: possibly increased risk of serotonergic effects - avoid. Dopaminergics: avoid use with entacapone; CNS toxicity reported with selegiline and rasagiline. Pentamidine: increased risk of ventricular arrhythmias. Sympathomimetics: increased risk of hypertension and arrhythmias with adrenaline and noradrenaline; metabolism possibly inhibited by methylphenidate.

Technology Process of Trimipramine

There total 3 articles about Trimipramine 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: 95.0%

trimipramine N-oxide (14171-70-1) → trimipramine (739-71-9)

Guidance literature:

With sodium tetrahydroborate; In water; at 50 - 60 ℃; chemoselective reaction;

DOI:10.1016/j.tetlet.2010.08.045

Reference yield:

9,10-dihydrodibenzazepine (494-19-9) + 3-(dimethylamino)-2-methylpropylchloride (23349-86-2) → trimipramine (739-71-9)

Guidance literature:

With sodium amide; In toluene; for 16h; Heating;

DOI:10.1002/mrc.1509

Reference yield:

→ trimipramine (739-71-9)

Guidance literature:

aus Iminodibenzyl-5-carbonsaeure-(3-dimethylamino-2-methyl-propylester) (185-250grad);

upstream raw materials:

9,10-dihydrodibenzazepine

3-(dimethylamino)-2-methylpropylchloride

trimipramine N-oxide

Downstream raw materials:

trimipramine N-oxide

Refernces

• 1、 Gowda, Narendra B.,Rao, Gopal Krishna,Ramakrishna, Ramesha A.. "A chemoselective deoxygenation of N-oxides by sodium borohydride-Raney nickel in water". experimental part. p. 5690 - 5693. Retrieved 2010/11/05.