Etorphinum

Base Information

• Chemical Name: Etorphinum
• CAS No.: 14521-96-1
• Molecular Formula: C25H33 N O4
• Molecular Weight: 411.541
• European Community (EC) Number: 238-535-9
• Wikipedia: Etorphine
• Wikidata: Q416827
• NCI Thesaurus Code: C80578
• Mol file: 14521-96-1.mol

Synonyms:Ethorphine;Etorphine;M99

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Chemical Property of Etorphinum

Chemical Property:

• Vapor Pressure: 6.47E-13mmHg at 25°C
• Melting Point: 217°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 549.7°C at 760 mmHg
• PKA: 12?+-.0.60(Predicted)
• Flash Point: 286.2°C
• PSA: 62.16000
• Density: 1.3g/cm³
• LogP: 3.10150
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 411.24095853
• Heavy Atom Count: 30
• Complexity: 772

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)C)OC)O
• Isomeric SMILES: CCCC(C)(C1C[C@@]23C=CC1(C4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)C)OC)O
• Uses: Etorphine is used as a narcotic analgesic.

Technology Process of Etorphinum

There total 13 articles about Etorphinum 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: 75.4%

etorphine methyl ether (16180-26-0) → etorphine (14521-96-1)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; heating;

DOI:10.1248/cpb.32.1268

Reference yield: 61.0%

1-[(5α,7α)-17-methyl-4,5-epoxy-3-hydroxy-6-methoxy-6,14-ethenomorphinan-7-yl]ethanone + 1-propylmagnesium chloride (2234-82-4) → etorphine (14521-96-1)

Guidance literature:

In 1,4-dioxane; diethyl ether; tert-butyl methyl ether; at 0 - 60 ℃; for 4.25h; Solvent;

Reference yield:

thevinone (15358-22-2) → etorphine (14521-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73.2 percent / diethyl ether; tetrahydrofuran / heating

2: 75.4 percent / EtSNa / dimethylformamide / heating

With sodium thioethylate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1248/cpb.32.1268

upstream raw materials:

etorphine methyl ether

thebaine

thevinone

N-carboethoxythebaine

Downstream raw materials:

(R)-2-(4,5α-epoxy-6-methoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-pentan-2-ol

Dihydroetorphine

S-etorphine

3-acetoxy-4,5α-epoxy-19anti-((R)-1-hydroxy-1-methyl-butyl)-6-methoxy-17-methyl-6β,14-ethano-morphin-7-ene

Refernces

• 1、 Huang, Xin-Ren,Srimurugan, Sankareswaran,Lee, Gene-Hsiang,Chena, Chinpiao. "A facile synthesis and structural verification of etorphine and dihydroetorphine from codeine". experimental part. p. 101 - 107. Retrieved 2011/11/28.
• 2、 -. "(+)-Isomers of endoetheno/endoethano-epoxymorphinan derivatives as antitussive agents". . . Retrieved 2008/06/13.