Cebranopadol

Base Information

• Chemical Name: Cebranopadol
• CAS No.: 863513-91-1
• Molecular Formula: C24H27FN2O
• Molecular Weight: 378.49
• UNII: 7GDW9S3GN3
• ChEMBL ID: CHEMBL2364605,CHEMBL3545616,CHEMBL3962932
• DSSTox Substance ID: DTXSID001031965
• Metabolomics Workbench ID: 153739
• NCI Thesaurus Code: C112002
• Pharos Ligand ID: HDDJAT77WTTU
• Wikidata: Q19596315
• Wikipedia: Cebranopadol
• Mol file: 863513-91-1.mol

Synonyms:6'-fluoro-4',9'-dihydro-N,N-dimethyl-4-phenylspiro(cyclohexane-1,1'(3'H)-pyrano(3,4-b)indol)-4-amine;cebranopadol

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Cebranopadol

Chemical Property:

• Boiling Point: 547.5±50.0 °C(Predicted)
• PKA: 16.79±0.40(Predicted)
• PSA: 28.26000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 5.10610
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 378.21074165
• Heavy Atom Count: 28
• Complexity: 553

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1(CCC2(CC1)C3=C(CCO2)C4=C(N3)C=CC(=C4)F)C5=CC=CC=C5
• Recent ClinicalTrials: Bunionectomy Trial With GRT6005
• Recent EU Clinical Trials: An open-label, multi-site trial to describe the safety and tolerability of oral cebranopadol administered for 26 weeks in subjects with cancer-related pain who have completed treatment in the KF6005/07 trial
• Uses: Cebranopadol can be obtained from 1,4-Cyclohexanedione Monoethylene Acetal (C987955) which is used in the preparation of series of potent analgesic compounds. 1,4-Cyclohexanedione Monoethylene Acetal (C987955) is also used as a building block in the synthesis of tritium labelled probes for the autoradiography study of the dopamine reuptake complex.

Technology Process of Cebranopadol

There total 5 articles about Cebranopadol 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: 91.0%

4-dimethylamino-4-phenylcyclohexanone (65619-20-7) + 2-(5-fluoro-1H-indol-3-yl)ethanol (101349-12-6) → (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine (863513-91-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 22 - 40 ℃; for 65h; Inert atmosphere;

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + C22H23FN2O → (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine (863513-91-1)

Guidance literature:

With formic acid; In water; at 70 ℃; for 16h;

DOI:10.1021/acs.orglett.0c02234

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine (863513-91-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / water; methanol / 0 - 20 °C

2.1: tetrahydrofuran / 0 - 20 °C

2.2: 0 - 20 °C

3.1: water; hydrogenchloride / diethyl ether

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 h / 20 °C / Inert atmosphere

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; water; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/ml500117c

upstream raw materials:

4-dimethylamino-4-phenylcyclohexanone

2-(5-fluoro-1H-indol-3-yl)ethanol

cyclohexanedione monoethylene ketal

8-(dimethylamino)-1,4-dioxaspiro-[4.5]-decane-8-carbonitrile

Downstream raw materials:

trans-6'-fluoro-4',9'-dihydro-N,N-dimethyl-4-phenyl-spiro[cyclohexane-1,1'(3'H)-pyrano[3,4-b]indol]-4-amine hemicitrate

(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine sulfate

(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine hydrochloride