Dizocilpine maleate

Base Information

• Chemical Name: Dizocilpine maleate
• CAS No.: 77086-22-7
• Molecular Formula: C₄H₄O₄*C₁₆H₁₅N
• Molecular Weight: 337.375
• European Community (EC) Number: 278-614-5
• UNII: 6LR8C1B66Q
• DSSTox Substance ID: DTXSID2045785
• Wikidata: Q27265120
• NCI Thesaurus Code: C166949
• ChEMBL ID: CHEMBL344151
• Mol file: 77086-22-7.mol

Synonyms:Dizocilpine;Dizocilpine Maleate;MK 801;MK-801;MK801

Chemical Property of Dizocilpine maleate

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 1.55E-12mmHg at 25°C
• Melting Point: 208.5-210°
• Boiling Point: 320.3 °C at 760 mmHg
• Flash Point: 152.6 °C
• PSA: 86.63000
• LogP: 3.19110
• Storage Temp.: Store at RT
• Solubility.: DMSO: >20 mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 337.13140809
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

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

(+)-MK-801 hydrogen maleate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CC12C3=CC=CC=C3CC(N1)C4=CC=CC=C24.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: C[C@@]12C3=CC=CC=C3C[C@@H](N1)C4=CC=CC=C24.C(=C\C(=O)O)\C(=O)O
• Uses: (-)-MK-801 MALEATE is probe for NMDA receptors (-)-MK-801 MALEATE acts as an NMDA receptor antagonist. It is selective and potent, but noncompetitive, used in various ischemia treatments. Dizocilpine maleate is used to interact at the NMDA-associated ion channel, preventing Ca2+ flux and blocking NMDA-induced depolarizations. (+)-MK 801 demonstrates potent neuroprotective effects against excitotoxic insult, showing substantial protection against neuron loss produced by NMDA and quinolinic acid introduction.

Technology Process of Dizocilpine maleate

There total 7 articles about Dizocilpine maleate 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: 79.0%

12-(4-methylphenylsulfonyl)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (76858-24-7) + maleic acid (110-16-7,26099-09-2) → MK-801 (77086-22-7)

Guidance literature:

12-(4-methylphenylsulfonyl)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine; With magnesium; triethylamine; In methanol; for 10h; Inert atmosphere; Reflux;

maleic acid; In methanol; water; for 10h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2012.03.007

Reference yield:

N-(4-methylphenylsulfonyl)-10,11-dihydro-5-oxo-dibenzo[a,d]cyclohepten-10,11-aziridine → MK-801 (77086-22-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 20 °C

2.1: tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice

3.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: magnesium; triethylamine / methanol / 10 h / Inert atmosphere; Reflux

4.2: 10 h / Inert atmosphere; Reflux

With palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; magnesium; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 2.1: Grignard methylation;

DOI:10.1016/j.tet.2012.03.007

Reference yield:

4-methyl-N-(5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl)-benzenesulfonamide (1372806-49-9) → MK-801 (77086-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice

2.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: magnesium; triethylamine / methanol / 10 h / Inert atmosphere; Reflux

3.2: 10 h / Inert atmosphere; Reflux

With boron trifluoride diethyl etherate; magnesium; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1.1: Grignard methylation;

DOI:10.1016/j.tet.2012.03.007

upstream raw materials:

12-(4-methylphenylsulfonyl)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine

maleic acid

4-methyl-N-(5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl)-benzenesulfonamide

dibenzosuberenon

Refernces

• 1、 -. "Process for 5-methyl-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5,10-imine". . . Retrieved 2008/06/13.