6-Acetylmorphine

Base Information

• Chemical Name: 6-Acetylmorphine
• CAS No.: 2784-73-8
• Molecular Formula: C19H21 N O4
• Molecular Weight: 327.38
• European Community (EC) Number: 621-729-6
• UNII: M5E47P1ZCH
• DSSTox Substance ID: DTXSID60182154
• Nikkaji Number: J330.682H
• Wikipedia: 6-Monoacetylmorphine
• Wikidata: Q2406967
• ChEMBL ID: CHEMBL592009
• Mol file: 2784-73-8.mol

Synonyms:6-(0-acetyl)morphine;6-acetylmorphine;6-MAM cpd;6-monoacetylmorphine;6-O-monoacetylmorphine;6-O-monoacetylmorphine hydrochloride, (5alpha,6alpha)-isomer;morphine-6-acetate

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of 6-Acetylmorphine

Chemical Property:

• Vapor Pressure: 1.83E-09mmHg at 25°C
• Melting Point: 184-189ºC
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 470.2°Cat760mmHg
• PKA: pKa 8.19 (H2O t=25.0±0.1 I=0.15(KCl) underAr) (Uncertain);9.55(H2O t=25.0±0.1 I=0.15(KCl) underAr) (Uncertain)
• Flash Point: 238.2°C
• PSA: 59.00000
• Density: 1.38g/cm³
• LogP: 1.70680
• Storage Temp.: −20°C
• XLogP3: 1.3
• 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:

Safty Information:

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)O)CCN3C
• Isomeric SMILES: CC(=O)O[C@H]1C=C[C@H]2[C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)O)CCN3C
• Uses: A metabolite of Heroin. Controlled substance

Technology Process of 6-Acetylmorphine

There total 4 articles about 6-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: 35.0%

methyl (phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosid)uronate (62812-42-4) + 3-O-acetylmorphine (5140-28-3) → 3-O-acetyl-6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucopyranosyluronate)morphine (20736-12-3) + 6-monoacetylmorphine (2784-73-8) + Diamorphine (561-27-3)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In diethyl ether; dichloromethane; at -12 ℃;

DOI:10.1055/s-2000-6413

Reference yield: 32.0%

ethyl [methyl(2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate] (99077-83-5) + 3-O-acetylmorphine (5140-28-3) → 3-O-acetyl-6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucopyranosyluronate)morphine (20736-12-3) + 6-monoacetylmorphine (2784-73-8) + Diamorphine (561-27-3)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In diethyl ether; dichloromethane; at -40 ℃;

DOI:10.1055/s-2000-6413

Reference yield:

Diamorphine (561-27-3) → MORPHIN (57-27-2) + 6-monoacetylmorphine (2784-73-8)

Guidance literature:

With water; at 37 ℃; half-lives at var. temp. and pH, also in the presence of human plasma; half-lives for 6-monoacetylmorphine;

DOI:10.1111/j.2042-7158.1992.tb05474.x

upstream raw materials:

heroin hydrochloride

Diamorphine

ethyl [methyl(2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]

3-O-acetylmorphine

Downstream raw materials:

Morphine 3-b-D-glucuronide

[3H]-Morphine 3-sulfate

Z-phenyl-2-azo-6-acetyl-morphine

E-phenyl-2-azo-6-acetyl-morphine

Refernces

• 1、 Barrett,Dyssegaard,Shaw. "The effect of temperature and pH on the deacetylation of diamorphine in aqueous solution and in human plasma". . p. 606 - 608. Retrieved 1992.
• 2、 Rukhman,Yudovich,Nisnevich,Gutman. "6-O-Glycosylation of morphine derivatives using thioglycosides as glycosyl donors". . p. 1241 - 1246. Retrieved 2007/10/03.