Nalfurafine

Base Information

• Chemical Name: Nalfurafine
• CAS No.: 152657-84-6
• Molecular Formula: C₂₈H₃₂N₂O₅
• Molecular Weight: 476.572
• UNII: XC41AVD567
• DSSTox Substance ID: DTXSID70905119
• Nikkaji Number: J934.315F
• Wikipedia: Nalfurafine
• Wikidata: Q6960874
• NCI Thesaurus Code: C80585
• Pharos Ligand ID: GAVFYSPDV7NU
• Metabolomics Workbench ID: 154277
• ChEMBL ID: CHEMBL267495
• Mol file: 152657-84-6.mol

Synonyms:17-cyclopropylmethyl-3,14beta-dihydroxy-4,5alpha-epoxy-6beta-(N-methyl-trans-3-(3-furyl)acrylamido)morphinan hydrochloride;nalfurafine;nalfurafine hydrochloride;TRK 820;TRK-820

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

Chemical Property of Nalfurafine

Chemical Property:

• Vapor Pressure: 1.3E-20mmHg at 25°C
• Boiling Point: 700.7°Cat760mmHg
• PKA: 9.37±0.60(Predicted)
• Flash Point: 377.6°C
• PSA: 86.38000
• Density: 1.41g/cm³
• LogP: 3.02760
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 476.23112213
• Heavy Atom Count: 35
• Complexity: 893

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C1CCC2(C3CC4=C5C2(C1OC5=C(C=C4)O)CCN3CC6CC6)O)C(=O)C=CC7=COC=C7
• Isomeric SMILES: CN([C@@H]1CC[C@]2([C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)O)CCN3CC6CC6)O)C(=O)/C=C/C7=COC=C7
• Recent EU Clinical Trials: CLINICAL TRIAL NO: EU820UPV01
• Recent NIPH Clinical Trials: Clinical trial to relapse of itching after the stop of nalfurafine for chronic hepatitis C, or cirrhosis.
• Uses: Treatment of uremic pruritus in hemodialysis patients.

Technology Process of Nalfurafine

There total 9 articles about Nalfurafine 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: 95.0%

→ 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[N-methyl-trans-3-(3-furyl)acrylamido]morphinan (152657-84-6)

Guidance literature:

Reference yield:

trans-3-(furan-3-yl)acryloyl chloride (81311-96-8) + 6β-N-methylnaltrexamine (102869-99-8) → 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[N-methyl-trans-3-(3-furyl)acrylamido]morphinan (152657-84-6)

Guidance literature:

In tetrahydrofuran; water; at 20 ℃; for 0.5h;

Reference yield:

17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6β-(N-methylamino)morphinan phthalate + trans-3-(furan-3-yl)acryloyl chloride (81311-96-8) → 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[N-methyl-trans-3-(3-furyl)acrylamido]morphinan (152657-84-6)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; for 0.5h; Inert atmosphere;

upstream raw materials:

6β-N-methylnaltrexamine

3-(furan-3-yl)prop-2-enoic acid

trans-3-(furan-3-yl)acryloyl chloride

(E)-3-furan-3-yl-acrylic acid

Downstream raw materials:

nalfurafine hydrochloride