Acetorphine

Base Information

• Chemical Name: Acetorphine
• CAS No.: 25333-77-1
• Molecular Formula: C27H35 N O5
• Molecular Weight: 453.579
• UNII: 2OGQ81529L
• ChEMBL ID: CHEMBL3989451
• DSSTox Substance ID: DTXSID60905123
• Metabolomics Workbench ID: 146124
• NCI Thesaurus Code: C79929
• Wikidata: Q1065083
• Wikipedia: Acetorphine
• Mol file: 25333-77-1.mol

Synonyms:ACETORPHINE;Acetorfina;25333-77-1;ACETYLPROPYLORVINOL;7.alpha.-etorphine 3-acetate;IDS-NA-001;2OGQ81529L;Acetorphinum;[(1R,2S,6R,14R,15R,19R)-19-[(2R)-2-hydroxypentan-2-yl]-15-methoxy-5-methyl-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,16-tetraen-11-yl] acetate;Acetorphine [INN:BAN];Acetorfina [INN-Spanish];Acetorphinum [INN-Latin];UNII-2OGQ81529L;BRN 4947728;ACETORPHINE [INN];7alpha-etorphine 3-acetate;SCHEMBL518296;DEA No. 9319;CHEMBL3989451;DTXSID60905123;IDS-NA-001(SECT.3);DB01469;6,7,8,14-Tetrahydro-7alpha-(1-hydroxy-1-methylbutyl)-6,14-endo-ethenooripavine 3-acetate;4,5alpha-Epoxy-7alpha-(1-hydroxy-1-methylbutyl)-6-methoxy-17-methyl-6,14-endo-ethenomorphinan-3-yl acetat;NS00068009;Q1065083;6,14-endo-Ethenotetrahydrooripavine, 7-alpha-(R)-(1-hydroxy-1-methylbutyl)-, 3-acetate;6,14-Ethenomorphinan-7-methanol, 3-(acetyloxy)-alpha,17-dimethyl-4,5-epoxy-6-methoxy-alpha-propyl-, (5-alpha,7-alpha(R))-;6,7,8,14-TETRAHYDRO-7.ALPHA.-(1-HYDROXY-1-METHYLBUTYL)-6,14-ENDO-ETHENOORIPAVINE 3-ACETATE;Acetorphine;6,14-Ethenomorphinan-7-methanol, 3-(acetyloxy)-4,5-epoxy-6-methoxy-?,17-dimethyl-?-propyl-, (?R,5?,7?)-;6,14-Ethenomorphinan-7-methanol, 3-(acetyloxy)-4,5-epoxy-6-methoxy-?,17-dimethyl-?-propyl-, [5?,7?(R)]-;6,14-endo-Ethenotetrahydrooripavine, 7?-(R)-(

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Chemical Property of Acetorphine

Chemical Property:

• Vapor Pressure: 6.92E-14mmHg at 25°C
• Boiling Point: 571.2°Cat760mmHg
• PKA: 14.92±0.29(Predicted)
• Flash Point: 299.2°C
• PSA: 68.23000
• Density: 1.28g/cm³
• LogP: 3.32120
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 453.25152322
• Heavy Atom Count: 33
• Complexity: 877

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)OC(=O)C)O4)C)OC)O
• Isomeric SMILES: CCC[C@](C)([C@H]1C[C@@]23C=C[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)OC(=O)C)O4)C)OC)O
• Use Description: Acetorphine is a potent synthetic opioid with various applications in different fields. In the field of veterinary medicine, it is employed as a veterinary tranquilizer and analgesic for the immobilization and sedation of wild or large animals during medical procedures or transport. Due to its powerful sedative properties, it is particularly useful for safely managing and treating animals without causing undue stress or harm. In the realm of pharmacology and research, acetorphine is used as a reference compound and tool in studies related to opioid receptors and pain management, contributing to our understanding of opioid pharmacology and potentially leading to the development of novel pain medications. Additionally, in some regions, acetorphine has been historically used for human anesthesia, but its human medical applications have become limited due to its high potency and potential for abuse. Its roles in veterinary medicine, research, and as a historical anesthetic highlight its significance in addressing pain management and advancing scientific knowledge in various fields.

Technology Process of Acetorphine

There total 2 articles about Acetorphine 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:

etorphine methyl ether (16180-26-0) → 3-acetoxy-4,5α-epoxy-19anti-((R)-1-hydroxy-1-methyl-butyl)-6-methoxy-17-methyl-6β,14-ethano-morphin-7-ene (25333-77-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: aq. NaOH

With potassium hydroxide; sodium hydroxide; In diethylene glycol;

DOI:10.1021/ja00989a032

Reference yield:

acetic anhydride (108-24-7) + etorphine (14521-96-1) → 3-acetoxy-4,5α-epoxy-19anti-((R)-1-hydroxy-1-methyl-butyl)-6-methoxy-17-methyl-6β,14-ethano-morphin-7-ene (25333-77-1)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja00989a032

upstream raw materials:

acetic anhydride

etorphine

etorphine methyl ether