Norhydromorphone

Base Information

• Chemical Name: Norhydromorphone
• CAS No.: 14696-23-2
• Molecular Formula: C16H17NO3
• Molecular Weight: 271.316
• DSSTox Substance ID: DTXSID70438654
• Nikkaji Number: J525.592I
• Wikidata: Q76415514
• Metabolomics Workbench ID: 42556
• Mol file: 14696-23-2.mol

Synonyms:norhydromorphone

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Chemical Property of Norhydromorphone

Chemical Property:

• Melting Point: 305-306 °C
• Boiling Point: 496.2±45.0 °C(Predicted)
• PKA: 9.03±0.20(Predicted)
• PSA: 58.56000
• Density: 1.44±0.1 g/cm3(Predicted)
• LogP: 1.61690
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 271.12084340
• Heavy Atom Count: 20
• Complexity: 467

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)C2C34C1C(CC5=C3C(=C(C=C5)O)O2)NCC4
• Isomeric SMILES: C1CC(=O)[C@H]2[C@@]34[C@@H]1[C@@H](CC5=C3C(=C(C=C5)O)O2)NCC4
• Uses: Norhydromorphone is a novel metabolite of Hydromorphone (H714650).

Technology Process of Norhydromorphone

There total 10 articles about Norhydromorphone 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: 38.0%

(S)-17-methyl-4,5α-epoxy-3-hydroxy-morphinan-6-one N-oxide → Norhydromorphone (14696-23-2)

Guidance literature:

With methanol; water; iron(II) sulfate; for 1h;

Reference yield:

hydromorphone (466-99-9) → Norhydromorphone (14696-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium bicarbonate / CHCl₃ / 5 h / Heating

2: zinc; aq. NaH₂PO₄ / tetrahydrofuran / 2.5 h / Heating

With sodium dihydrogenphosphate; potassium hydrogencarbonate; zinc; In tetrahydrofuran; chloroform;

DOI:10.1016/j.lfs.2004.06.008

Reference yield:

(-)-4,5-epoxy-3-hydroxy-N-(2,2,2-trichloroethoxycarbonyl)morphinan-6-one (85618-66-2) → Norhydromorphone (14696-23-2)

Guidance literature:

With sodium dihydrogenphosphate; zinc; In tetrahydrofuran; for 2.5h; Heating;

DOI:10.1016/j.lfs.2004.06.008

upstream raw materials:

normorphine

(-)-4,5-epoxy-3-hydroxy-N-(2,2,2-trichloroethoxycarbonyl)morphinan-6-one

hydromorphone

(-)-tetrahydrothebaine