Desipramine

Base Information

• Chemical Name: Desipramine
• CAS No.: 50-47-5
• Molecular Formula: C18H22 N2
• Molecular Weight: 266.386
• Hs Code.: 2933990090
• European Community (EC) Number: 200-040-0
• UNII: TG537D343B
• DSSTox Substance ID: DTXSID6022896
• Nikkaji Number: J8.596K
• Wikipedia: Desipramine
• Wikidata: Q423288
• NCI Thesaurus Code: C61700
• RXCUI: 3247
• Pharos Ligand ID: DQYTJFUGMG5V
• Metabolomics Workbench ID: 43373
• ChEMBL ID: CHEMBL72
• Mol file: 50-47-5.mol

Synonyms:Apo Desipramine;Apo-Desipramine;Demethylimipramine;Desipramine;Desipramine Hydrochloride;Desmethylimipramine;Hydrochloride, Desipramine;Norpramin;Novo Desipramine;Novo-Desipramine;Nu Desipramine;Nu-Desipramine;Pertofran;Pertofrane;Pertrofran;Petylyl;PMS Desipramine;PMS-Desipramine;Ratio Desipramine;ratio-Desipramine

Chemical Property of Desipramine

Chemical Property:

• Melting Point: 212°C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 407.4 °C at 760 mmHg
• PKA: pKa 10.21(-)(H2O t=20) (Uncertain)
• Flash Point: 160.5 °C
• PSA: 15.27000
• Density: 1.047 g/cm³
• LogP: 3.98870
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 266.178298710
• Heavy Atom Count: 20
• Complexity: 267

Purity/Quality:

99.9% ^*data from raw suppliers

Desipramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressants
• Canonical SMILES: CNCCCN1C2=CC=CC=C2CCC3=CC=CC=C31
• Recent ClinicalTrials: Irritable Bowel Syndrome (IBS) Functional Magnetic Resonance Imaging (fMRI) With Desipramine
• Recent EU Clinical Trials: A Randomized Phase 4 Study Comparing 2 Intravenous Temsirolimus (TEMSR) Regimens in Subjects With Relapsed, Refractory Mantle Cell Lymphoma
• Uses: Desipramine is used for depression of various etiology and in particular for endogenous depression. Antidepressant.
• Therapeutic Function: Psychostimulant

Technology Process of Desipramine

There total 24 articles about Desipramine 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: 75.0%

N-Benzyldesipramine (3978-87-8) → desipramine (50-47-5)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 60 ℃; for 16h; under 760.051 Torr;

DOI:10.1021/acscatal.1c01199

Reference yield: 44.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + didesmethylimipramine (2095-95-6) → desipramine (50-47-5)

Guidance literature:

formaldehyd; In methanol; at 20 ℃; for 0.25h;

didesmethylimipramine; With methanol; sodium tetrahydroborate; at 80 ℃; for 0.666667h; Microwave irradiation;

DOI:10.1021/acschemneuro.8b00242

Reference yield:

Imipramine hydrochloride (113-52-0) → desipramine (50-47-5) + 9,10-dihydrodibenzazepine (494-19-9) + 10-Hydroxyimipramine (796-28-1)

Guidance literature:

In water; Ambient temperature; M_. griseo-cyanus (ATCC 1207a); further microbial agents;

DOI:10.1002/jps.2600700209

upstream raw materials:

10,11-dihydro-N-methyl-N-(methyl-d₃)-5H-dibenz(b,f)azepine-5-propanamine

impramine

Imipramine hydrochloride

2-((2Ξ,4S)-3,4r-dimethyl-5c-phenyl-oxazolidin-2-yl)-phenol

Downstream raw materials:

impramine

cyclopropylcarbinyl bromide

3-phenoxybenzyl 2-(4-difluorochloromethoxyphenyl)-2-methylpropyl ether

N'-(4-{[3-(10,11-dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-amino}phenyl)-diazocarboxylic acid tert-butyl ester

Refernces

• 1、 Clark,Clinton,Baker,Hufford. "Demethylation of imipramine by enteric bacteria". . p. 1288 - 1290. Retrieved 1983.
• 2、 Cheng, Fangyuan,Du, Lei,Durairaj, Pradeepraj,Guo, Jiawei,Li, Fengwei,Li, Shengying,Liu, Xiaohui,Long, Xiangtian,Ma, Li,Tang, Dandan,Zhang, Gang,Zhang, Wei,Zhang, Xingwang. "Bacterial Biosynthetic P450 Enzyme PikCD50N: A Potential Biocatalyst for the Preparation of Human Drug Metabolites". . p. 14563 - 14571. Retrieved 2021/11/12.
• 3、 Blaess, Markus,Bibak, Nelly,Claus, Ralf A.,Kohl, Matthias,Bonaterra, Gabriel A.,Kinscherf, Ralf,Laufer, Stefan,Deigner, Hans-Peter. "NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation". . p. 73 - 104. Retrieved 2017/10/17.