Naltrindole

Base Information

• Chemical Name: Naltrindole
• CAS No.: 111555-53-4
• Molecular Formula: C26H26 N2 O3
• Molecular Weight: 414.5
• UNII: G167Z38QA4
• DSSTox Substance ID: DTXSID60912216
• Nikkaji Number: J304.821G
• Wikipedia: Naltrindole
• Wikidata: Q3743642
• Pharos Ligand ID: JNZ47ZTMRPPG
• ChEMBL ID: CHEMBL567175
• Mol file: 111555-53-4.mol

Synonyms:17-cyclopropylmethyl-6,7-dehydro-4,5-epoxy-3,14-dihydroxy-6,7,2',3'-indolomorphinan;naltrindole;natrindole hydrochloride

Chemical Property of Naltrindole

Chemical Property:

• Vapor Pressure: 1.23E-17mmHg at 25°C
• Boiling Point: 647.2°Cat760mmHg
• Flash Point: 345.2°C
• PSA: 68.72000
• Density: 1.51g/cm³
• LogP: 3.51050
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 414.19434270
• Heavy Atom Count: 31
• Complexity: 774

Purity/Quality:

NALTRINDOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1CN2CCC34C5C6=C(CC3(C2CC7=C4C(=C(C=C7)O)O5)O)C8=CC=CC=C8N6
• Isomeric SMILES: C1CC1CN2CC[C@]34[C@@H]5C6=C(C[C@]3([C@H]2CC7=C4C(=C(C=C7)O)O5)O)C8=CC=CC=C8N6

Technology Process of Naltrindole

There total 7 articles about Naltrindole 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: 98.0%

naltrexone Hydrochloride (16676-29-2) + phenylhydrazine hydrochloride (59-88-1) → naltrindole (111555-53-4)

Guidance literature:

In water; at 20 ℃;

DOI:10.1039/b920864j

Reference yield: 98.0%

naltrexone Hydrochloride (16676-29-2) + phenylhydrazine (100-63-0) → naltrindole (111555-53-4)

Guidance literature:

In water; at 100 ℃; for 0.75h; Acidic conditions;

DOI:10.1002/jlcr.3898

Reference yield: 82.0%

3-O-Methylnaltrindole (126580-44-7) → naltrindole (111555-53-4)

Guidance literature:

With L-Selectride; In tetrahydrofuran; for 4h; Heating;

DOI:10.1021/jo9801972

upstream raw materials:

naltrexone Hydrochloride

phenylhydrazine hydrochloride

3-O-Methylnaltrindole

Naltrexone

Downstream raw materials:

17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-6,7-2',3'-indolomorphinan

17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-6,7-2',3'-indolomorphinan

3-O-triphenylmethylnaltrindole

17-cyclopropylmethyl-6,7-didehydro-4,5-epoxy-3-benzyloxy-14-hydroxy-6,7,2',3'-[1'-(p-fluorobenzyl)]-indolomorphinan

Refernces

Fischer indole synthesis in water: Simple, efficient preparation of naltrindole, naltriben and analogs

10.1039/b920864j

The research presents an environmentally friendly method for synthesizing naltrindole (NTI), naltriben (NTB), and their analogs using Fischer indole synthesis under mildly acidic, purely aqueous conditions. The study explores the preparation of these compounds, which are valuable tools for opioid receptor pharmacology studies, using hydrochloride salts of naltrexone and various phenylhydrazines in boiling water, achieving good to excellent yields and high purities without the need for organic solvents or harsh acids. The chemicals that played a crucial role in this research include naltrexone hydrochloride (NTX·HCl), phenylhydrazine hydrochloride, and other substituted phenylhydrazines such as 1-methyl-1-phenylhydrazine, o-chlorophenylhydrazine, o-fluorophenylhydrazine, and o-nitrophenylhydrazine. The study also utilized dilute hydrochloric acid (HCl) to facilitate the synthesis, and in some cases, sulfuric acid (H?SO?) for comparison. The products were obtained through simple filtration or centrifugation, highlighting the simplicity and efficiency of the aqueous Fischer synthesis method.