N-Methylnaltrindole

Base Information

• Chemical Name: N-Methylnaltrindole
• CAS No.: 111555-57-8
• Molecular Formula: C27H28 N2 O3
• Molecular Weight: 428.52
• UNII: M993BKL35V
• DSSTox Substance ID: DTXSID20912217
• Nikkaji Number: J328.064K
• Wikidata: Q27283696
• Pharos Ligand ID: QQH7AHNJZBWZ
• ChEMBL ID: CHEMBL477154
• Mol file: 111555-57-8.mol

Synonyms:N-methylnaltrindole

Chemical Property of N-Methylnaltrindole

Chemical Property:

• Vapor Pressure: 1.47E-17mmHg at 25°C
• Boiling Point: 645.8°Cat760mmHg
• Flash Point: 344.4°C
• PSA: 57.86000
• Density: 1.57g/cm³
• LogP: 3.52090
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 428.20999276
• Heavy Atom Count: 32
• Complexity: 804

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C3=C1C4C56CCN(C(C5(C3)O)CC7=C6C(=C(C=C7)O)O4)CC8CC8
• Isomeric SMILES: CN1C2=CC=CC=C2C3=C1[C@H]4[C@@]56CCN([C@@H]([C@@]5(C3)O)CC7=C6C(=C(C=C7)O)O4)CC8CC8

Technology Process of N-Methylnaltrindole

There total 6 articles about N-Methylnaltrindole 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: 73.0%

naltrexone Hydrochloride (16676-29-2) + 1-Methyl-1-phenylhydrazine (618-40-6) → N-Methylnaltrindole (111555-57-8)

Guidance literature:

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

DOI:10.1002/jlcr.3898

Reference yield: 31.0%

17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-6,7-2',3'-(1'-methyl)-indolomorphinan (161532-23-6) → N-Methylnaltrindole (111555-57-8)

Guidance literature:

With hydrogen; ammonium formate; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; at 85 ℃; for 0.166667h;

DOI:10.1002/jlcr.2580360206

Reference yield: 4.0%

17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-5',7'-dibromo-6,7-2',3'-(1'-methyl)-indolomorphinan (188258-72-2) → N-Methylnaltrindole (111555-57-8) + C27H27BrN2O3

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In N,N-dimethyl-formamide; for 2h; under 258.6 Torr; Ambient temperature;

DOI:10.1002/(SICI)1099-1344(199702)39:2<115::AID-JLCR947>3.0.CO;2-3

upstream raw materials:

naltrexone Hydrochloride

N-methyl-N-phenylhydrazine hydrochloride

17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-6,7-2',3'-(1'-methyl)-indolomorphinan

17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-5',7'-dibromo-6,7-2',3'-(1'-methyl)-indolomorphinan

Downstream raw materials:

17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-6,7-2',3'-(1'-methyl)-indolomorphinan