Dizocilpine, (-)-

Base Information

• Chemical Name: Dizocilpine, (-)-
• CAS No.: 77086-19-2
• Molecular Formula: C₁₆H₁₅N
• Molecular Weight: 221.302
• Hs Code.: 2925290090
• UNII: 2V2JET5YTL
• DSSTox Substance ID: DTXSID901018023
• Nikkaji Number: J403.264K
• Wikidata: Q27166385
• ChEMBL ID: CHEMBL132153
• Mol file: 77086-19-2.mol

Synonyms:Dizocilpine, (-)-;(-)-dizocilpine;2V2JET5YTL;Dizocilpine (-)-form [MI];UNII-2V2JET5YTL;(+)-5-Methyl-10,11- dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine maleate);(1R,9S)-1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaene;5H-Dibenzo(a,d)cyclohepten-5,10-imine, 10,11-dihydro-5-methyl-, (5R,10S)-;dizocilpine-(-);MK-801(Dizocilpine);Prestwick0_000935;Prestwick1_000935;Prestwick2_000935;Prestwick3_000935;BSPBio_000870;SPBio_003039;BPBio1_000958;CHEMBL132153;SCHEMBL4029994;CHEBI:94547;DTXSID901018023;HMS3267G17;AB00514720;BRD-K23163214-050-03-7;Q27166385

Chemical Property of Dizocilpine, (-)-

Chemical Property:

• Melting Point: 68.5-69.5°
• PSA: 86.63000
• LogP: 3.19110
• Storage Temp.: 0-6°C
• Solubility.: DMSO: >20mg/mL
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 221.120449483
• Heavy Atom Count: 17
• Complexity: 313

Purity/Quality:

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

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C3=CC=CC=C3CC(N1)C4=CC=CC=C24
• Isomeric SMILES: C[C@]12C3=CC=CC=C3C[C@H](N1)C4=CC=CC=C24
• Uses: Biochemical probe for NMDA receptors.

Technology Process of Dizocilpine, (-)-

There total 8 articles about Dizocilpine, (-)- 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: 97.0%

C21H24N2 (124070-25-3) → (+/-)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (70449-94-4,77086-18-1,77086-19-2,77086-21-6)

Guidance literature:

With potassium hydroxide; In ethylene glycol; at 150 ℃; for 0.25h;

DOI:10.1016/S0040-4039(00)95276-6

Reference yield: 83.0%

5-methyl-12-((trifluoromethyl)sulfonyl)-10,11-dihydro-5H-5,10-epiminodibenzo[7]annulene → (+/-)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (70449-94-4,77086-18-1,77086-19-2,77086-21-6)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 0 - 50 ℃; for 14h; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201901673

Reference yield:

(+/-)-des-methyl MK-801 (50537-17-2,129746-23-2) → (+/-)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (70449-94-4,77086-18-1,77086-19-2,77086-21-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / (NH₄)2SO₄

2: 1.) s-BuLi / 1.) Et₂O, 5-10 deg C, 30 min 2.) 5-10 deg C to room temp.

3: 97 percent / KOH / ethane-1,2-diol / 0.25 h / 150 °C

With potassium hydroxide; sec.-butyllithium; ammonium sulfate; In ethylene glycol;

DOI:10.1016/S0040-4039(00)95276-6

upstream raw materials:

C₂₁H₂₄N₂

(+/-)-des-methyl MK-801

C₂₀H₂₂N₂

10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Downstream raw materials:

(5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine

Refernces

• 1、 Monn, J. A.,Rice, K. C.. "A BRIDGEHEAD α-AMINO CARBANION: FACILE PREPARATION OF C5(BRIDGEHEAD)-SUBSTITUTED ANALOGUES OF (+/-)-5H-DIBENZOCYCLOHEPTEN-5,10-IMINE INCLUDING A STABLE α-IODO SECONDARY AMINE". . p. 911 - 914. Retrieved 2007/10/02.