Moclobemide

Base Information

• Chemical Name: Moclobemide
• CAS No.: 71320-77-9
• Molecular Formula: C13H17ClN2O2
• Molecular Weight: 268.743
• Hs Code.: 29349990
• European Community (EC) Number: 636-108-5
• UNII: PJ0Y7AZB63
• DSSTox Substance ID: DTXSID9040554
• Nikkaji Number: J19.047K
• Wikipedia: Moclobemide
• Wikidata: Q421934
• NCI Thesaurus Code: C87772
• Pharos Ligand ID: B46BM9JVTFNP
• Metabolomics Workbench ID: 43389
• ChEMBL ID: CHEMBL86304
• Mol file: 71320-77-9.mol

Synonyms:Apo Moclobemide;Apo-Moclobemide;Arima;Aurorex;Aurorix;AZU, Moclobemid;Chem mart Moclobemide;DBL Moclobemide;Deprenorm;Feraken;GenRX Moclobemide;Healthsense Moclobemide;Manerix;Moclamine;Moclix;Moclobamide;Moclobemid 1A Pharma;Moclobemid AZU;Moclobemid Puren;Moclobemid ratiopharm;Moclobemid Stada;Moclobemid von ct;Moclobemid-1A Pharma;Moclobemid-Puren;Moclobemid-ratiopharm;Moclobemid1A Pharma;Moclobemide;Moclobemide, Chem mart;Moclobemide, DBL;Moclobemide, GenRX;Moclobemide, Healthsense;Moclobeta;Moclodura;Moclonorm;Novo Moclobemide;Novo-Moclobemide;NovoMoclobemide;Nu Moclobemide;Nu-Moclobemide;NuMoclobemide;PMS Moclobemide;PMS-Moclobemide;Rimoc;Ro 11 1163;Ro 11-1163;Ro-11-1163;Stada, Moclobemid;Terry White Chemists Moclobemide;von ct, Moclobemid

Chemical Property of Moclobemide

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 3.29E-08mmHg at 25°C
• Melting Point: 137 °C
• Refractive Index: 1.55
• Boiling Point: 447.7 °C at 760 mmHg
• PKA: 14.26±0.46(Predicted)
• Flash Point: 224.6 °C
• PSA: 41.57000
• Density: 1.206 g/cm³
• LogP: 1.73080
• Storage Temp.: Room temp
• Solubility.: DMSO: >20mg/mL
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 268.0978555
• Heavy Atom Count: 18
• Complexity: 262

Purity/Quality:

98% ^*data from raw suppliers

Moclobemide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T+
• Hazard Codes: Xn,T+
• Statements: 22-37/38-41-26/27/28
• Safety Statements: 26-39-45-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1CCNC(=O)C2=CC=C(C=C2)Cl
• Recent ClinicalTrials: Establishment of Cessation Therapy by Clinical Trials for Subjects With Betel-quid Dependence and Oral Pre-cancer
• Recent EU Clinical Trials: Evaluation médico-économique de l’infusion continue intra-duodénale d’une forme gélifiée de levodopa dans le traitement des formes avancées et sévères de maladie de parkinson par l’intermédiaire d’un dispositif médical
• Description: Moclobemide is the first of a new generation of non-hydrazine, reversible MAO-A inhibitors useful in the treatment of depression. Moclobemide is a selective inhibitor of MAO-A, allowing tyramine to be metabolized by MAO-B. In controlled studies, moclobemide was clinically superior to desipramine and showed no cholinergic or cardiovascular side-effects. A metabolite is currently under investigation for treatment of Parkinson’s disease,. Moclobemide (Item No. 24361) is an analytical reference standard categorized as an antidepressant. This product is intended for research and forensic applications.
• Uses: A reversible monoamine oxidase inhibitor Antidepressant;Mono amine oxidase inhibitor (Type A) A reversible monoamine oxidase inhibitor.
• Clinical Use: Reversible MAOI: Depression Social phobia
• Drug interactions: Drug interactions for the RIMAs include interaction with SSRI antidepressants, which can cause the 5-HT syndrome. The effect of stimulant drugs, such as methylphenidate and dextroamphetamine (used to treat ADHD), may be increased. Some over-the-counter cold and hay fever decongestants (i.e., sympathomimetic amines) can have increased stimulant effects. Selegiline, a selective MAO-B used for Parkinson's disease, should not be used concurrently with the RIMAs. Unlike the irreversible MAOIs, no significant interactions with foods occur, because the selective inhibition of MAO-A does not stop the metabolism of tyramine. The RIMAs must not be taken concurrently with a nonreversible MAOI.

Technology Process of Moclobemide

There total 47 articles about Moclobemide 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: 100.0%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + para-chlorobenzoic acid (74-11-3) → moclobemide (71320-77-9)

Guidance literature:

With tetramethylorthosilicate; In toluene; at 110 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03841

Reference yield: 99.0%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + Methyl 4-chlorobenzoate (1126-46-1) → moclobemide (71320-77-9)

Guidance literature:

With sodium t-butanolate; In neat (no solvent); at 20 ℃; for 1h; Inert atmosphere; Schlenk technique; Green chemistry;

DOI:10.1039/d1gc00720c

Reference yield: 99.0%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 1-Chloro-4-iodobenzene (637-87-6) + chloroform (67-66-3,8013-54-5) → moclobemide (71320-77-9)

Guidance literature:

With cesiumhydroxide monohydrate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; In toluene; at 80 ℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.5b01385

upstream raw materials:

4-(2-AMINOETHYL)MORPHOLINE

4-chloro-benzoyl chloride

para-chlorobenzoic acid

4-chlorobenzaldehyde

Downstream raw materials:

Ro 12-5637

Refernces

• 1、 Kim, Dokyoung,Sambasivan, Sunderraman,Nam, Hyoseok,Ki, Hean Kim,Jin, Yong Kim,Joo, Taiha,Lee, Kyung-Ha,Kim, Kyong-Tai,Han Ahn, Kyo. "Reaction-based two-photon probes for in vitro analysis and cellular imaging of monoamine oxidase activity". . p. 6833 - 6835. Retrieved 2012.
• 2、 Liu, Tao,Zhang, Xue,Peng, Zejun,Zhao, Junfeng. "Water-removable ynamide coupling reagent for racemization-free syntheses of peptides, amides, and esters". supporting information. p. 9916 - 9921. Retrieved 2021/12/24.
• 3、 Rashed, Md. Nurnobi,Masuda, Koichiro,Ichitsuka, Tomohiro,Koumura, Nagatoshi,Sato, Kazuhiko,Kobayashi, Shū. "Zirconium Oxide-Catalyzed Direct Amidation of Unactivated Esters under Continuous-Flow Conditions". . p. 2529 - 2535. Retrieved 2021/02/01.