Cyprenorphine

Base Information

• Chemical Name: Cyprenorphine
• CAS No.: 4406-22-8
• Deprecated CAS: 17065-88-2,24472-80-8
• Molecular Formula: C₂₆H₃₃NO₄
• Molecular Weight: 423.552
• UNII: 1P6HEG5ZHS
• ChEMBL ID: CHEMBL2110789
• DSSTox Substance ID: DTXSID80905125
• Metabolomics Workbench ID: 146135
• NCI Thesaurus Code: C87355
• Wikidata: Q5200299
• Wikipedia: Cyprenorphine
• Mol file: 4406-22-8.mol

Synonyms:cyprenorphine

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Chemical Property of Cyprenorphine

Chemical Property:

• Melting Point: 234° (7a- or 7b-linkage unspecified)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 62.16000
• Density: 1.35g/cm³
• LogP: 3.10150
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 423.24095853
• Heavy Atom Count: 31
• Complexity: 824

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O
• Isomeric SMILES: CC(C)([C@H]1C[C@@]23C=C[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O
• Uses: Cyprenorphine is an Etorphine(E936500) antagonist, which is an opioid analgesic and anesthetic used as strong tranquilizer for large animals. Cyprenorphine has been studied for its use as an opioid addition treatment and an analgesic.Controlled substance (opium derivatives)

Technology Process of Cyprenorphine

There total 7 articles about Cyprenorphine 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:

2-(3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-propan-2-ol → N-cyclopropylmethyl-6,14-endo-etheno-7-(2-hydroxy-2-propyl)tetrahydronororipavine (4406-22-8)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂

2: KOH / bis-(2-hydroxy-ethyl) ether

3: K₂CO₃ / diethyl ether

4: LiAlH₄ / tetrahydrofuran / Heating

With potassium hydroxide; lithium aluminium tetrahydride; potassium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; diethylene glycol;

DOI:10.1021/ja00989a032

Reference yield:

4,5α-epoxy-19anti-(1-hydroxy-1-methyl-ethyl)-3,6-dimethoxy-6β,14-ethano-morphin-7-ene-17-carbonitrile (16553-46-1) → N-cyclopropylmethyl-6,14-endo-etheno-7-(2-hydroxy-2-propyl)tetrahydronororipavine (4406-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1: KOH / bis-(2-hydroxy-ethyl) ether

2: K₂CO₃ / diethyl ether

3: LiAlH₄ / tetrahydrofuran / Heating

With potassium hydroxide; lithium aluminium tetrahydride; potassium carbonate; In tetrahydrofuran; diethyl ether; diethylene glycol;

DOI:10.1021/ja00989a032

Reference yield:

17-cyclopropanecarbonyl-4,5α-epoxy-19anti-(1-hydroxy-1-methyl-ethyl)-6-methoxy-6β,14-ethano-morphin-7-en-3-ol (16550-20-2) → N-cyclopropylmethyl-6,14-endo-etheno-7-(2-hydroxy-2-propyl)tetrahydronororipavine (4406-22-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Heating;

DOI:10.1021/ja00989a032

upstream raw materials:

17-cyclopropanecarbonyl-4,5α-epoxy-19anti-(1-hydroxy-1-methyl-ethyl)-6-methoxy-6β,14-ethano-morphin-7-en-3-ol

7α-(1-hydroxy-1-methylethyl)-6,7,8,14-tetrahydro-6,14-endo-ethenothebaine

2,2'-[4,5α;4',5'α-diepoxy-3,6,3',6'-tetramethoxy-17,17'-methanediyl-bis-(6α,14α-etheno-morphinan-7α-yl)]-bis-propan-2-ol

4,5α-epoxy-19anti-(1-hydroxy-1-methyl-ethyl)-6-methoxy-6β,14-ethano-morphin-7-en-3-ol