3-Acetylmorphine

Base Information

• Chemical Name: 3-Acetylmorphine
• CAS No.: 5140-28-3
• Molecular Formula: C19H21 N O4
• Molecular Weight: 327.38
• European Community (EC) Number: 682-868-6
• UNII: 9N7243EY5T
• DSSTox Substance ID: DTXSID30183774
• Nikkaji Number: J276.364H
• Wikipedia: 3-Monoacetylmorphine
• Wikidata: Q4634178
• Mol file: 5140-28-3.mol

Synonyms:O(3)-monoacetylmorphine;O(3)-monoacetylmorphine hydrochloride, (5alpha,6alpha)-isomer;O(3)-monoacetylmorphine, sulfamate, (5alpha,6alpha)-isomer

Chemical Property of 3-Acetylmorphine

Chemical Property:

• Vapor Pressure: 3.65E-14mmHg at 25°C
• Boiling Point: 621.3°Cat760mmHg
• Flash Point: 329.5°C
• PSA: 59.00000
• Density: 1.195g/cm³
• LogP: 1.35570
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 327.14705815
• Heavy Atom Count: 24
• Complexity: 592

Purity/Quality:

99%min ^*data from raw suppliers

3-Acetylmorphine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=C2C3=C(CC4C5C3(CCN4C)C(O2)C(C=C5)O)C=C1
• Isomeric SMILES: CC(=O)OC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4C)[C@@H](O2)[C@H](C=C5)O)C=C1

Technology Process of 3-Acetylmorphine

There total 5 articles about 3-Acetylmorphine 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: 99.0%

acetic anhydride (108-24-7) + MORPHIN (57-27-2) → 3-O-acetylmorphine (5140-28-3)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 0.25h;

DOI:10.1016/j.ejmech.2018.02.074

Reference yield: 98.0%

morphine hydrochloride (52-26-6) + acetic anhydride (108-24-7) → 3-O-acetylmorphine (5140-28-3)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃;

DOI:10.1016/j.ejmech.2013.09.031

Reference yield: 90.0%

morphine sulfate (64-31-3,49719-65-5,6211-15-0) + acetic anhydride (108-24-7) → 3-O-acetylmorphine (5140-28-3)

Guidance literature:

With sodium hydrogencarbonate; In water;

upstream raw materials:

acetic anhydride

MORPHIN

acetic acid

morphine hydrochloride

Downstream raw materials:

morphine

N-methyl 7,8-didehydro-4,5-epoxy-3,6-dihydroxy-(5α,6α)-morphinan carbamate

N-methyl 3,6-diacetyl-7,8-didehydro-4,5-epoxy(5α,6α)-morphinan carbamate

6β-(4-(trifluoromethyl)cinnamoyl)-morphinamine

Refernces

• 1、 Ahonen, Tiina J.,Rinne, Maiju,Grutschreiber, Peter,M?tlik, Kert,Airavaara, Mikko,Schaarschmidt, Dieter,Lang, Heinrich,Reiss, David,Xhaard, Henri,Gaveriaux-Ruff, Claire,Yli-Kauhaluoma, Jari,Moreira, Vania M.. "Synthesis of 7β-hydroxy-8-ketone opioid derivatives with antagonist activity at mu- and delta-opioid receptors". . p. 495 - 507. Retrieved 2018/04/14.
• 2、 Váradi, András,Hosztafi, Sándor,Le Rouzic, Valerie,Tóth, Gergo,Urai, ákos,Noszál, Béla,Pasternak, Gavril W.,Grinnell, Steven G.,Majumdar, Susruta. "Novel 6β-acylaminomorphinans with analgesic activity". supporting information. p. 786 - 789. Retrieved 2013/10/22.