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Literature DB >> 833816

A rapid, high-yield conversion of codeine to morphine.

Abstract

Brief treatment of codeine (1) in chloroform with boron tribromide has consiste-tly given morphine (2) in 90-91% yield after a simple isolation procedure. The yield and simplicity of operation in this method are vastly superior to those previously reported for this transformation.

Entities: Chemical

Mesh：

Substances：

Year: 1977 PMID： 833816 DOI： 10.1021/jm00211a036

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

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Cited

12 in total

1. Structural determinants of opioid activity in derivatives of 14-aminomorphinones: effect of substitution in the aromatic ring of cinnamoylaminomorphinones and codeinones.

Authors: Nick P R Nieland; Humphrey A Moynihan; Simon Carrington; Jillian Broadbear; James H Woods; John R Traynor; Stephen M Husbands; John W Lewis
Journal: J Med Chem Date: 2006-08-24 Impact factor: 7.446

2. Benzylideneoxymorphone: A new lead for development of bifunctional mu/delta opioid receptor ligands.

Authors: Jason R Healy; Padmavani Bezawada; Nicholas W Griggs; Andrea L Devereaux; Rae R Matsumoto; John R Traynor; Andrew Coop; Christopher W Cunningham
Journal: Bioorg Med Chem Lett Date: 2016-11-22 Impact factor: 2.823

3. A One-Step Synthesis of β-Bromocodide from Codeine.

Authors: Christopher W Cunningham; Jeffrey R Deschamps; Andrew Coop
Journal: J Pharm Sci Pharmacol Date: 2014-03

4. Synthesis, modeling, and pharmacological evaluation of UMB 425, a mixed μ agonist/δ antagonist opioid analgesic with reduced tolerance liabilities.

Authors: Jason R Healy; Padmavani Bezawada; Jihyun Shim; Jace W Jones; Maureen A Kane; Alexander D MacKerell; Andrew Coop; Rae R Matsumoto
Journal: ACS Chem Neurosci Date: 2013-06-11 Impact factor: 4.418

5. Synthesis and immunological effects of heroin vaccines.

Authors: Fuying Li; Kejun Cheng; Joshua F G Antoline; Malliga R Iyer; Gary R Matyas; Oscar B Torres; Rashmi Jalah; Zoltan Beck; Carl R Alving; Damon A Parrish; Jeffrey R Deschamps; Arthur E Jacobson; Kenner C Rice
Journal: Org Biomol Chem Date: 2014-10-07 Impact factor: 3.876

6. Opioids and efflux transporters. Part 3: P-glycoprotein substrate activity of 3-hydroxyl addition to meperidine analogs.

Authors: Susan L Mercer; Christopher W Cunningham; Natalie D Eddington; Andrew Coop
Journal: Bioorg Med Chem Lett Date: 2008-04-25 Impact factor: 2.823

A rapid, high-yield conversion of codeine to morphine.

1. Structural determinants of opioid activity in derivatives of 14-aminomorphinones: effect of substitution in the aromatic ring of cinnamoylaminomorphinones and codeinones.

2. Benzylideneoxymorphone: A new lead for development of bifunctional mu/delta opioid receptor ligands.

3. A One-Step Synthesis of β-Bromocodide from Codeine.

4. Synthesis, modeling, and pharmacological evaluation of UMB 425, a mixed μ agonist/δ antagonist opioid analgesic with reduced tolerance liabilities.

5. Synthesis and immunological effects of heroin vaccines.

6. Opioids and efflux transporters. Part 3: P-glycoprotein substrate activity of 3-hydroxyl addition to meperidine analogs.

7. Opioids and efflux transporters. Part 2: P-glycoprotein substrate activity of 3- and 6-substituted morphine analogs.

Review 8. The DARK Side of Total Synthesis: Strategies and Tactics in Psychoactive Drug Production.

9. A Cascade Strategy Enables a Total Synthesis of (±)-Morphine.

10. Design, Synthesis, and Biological Evaluation of Phenol Bioisosteric Analogues of 3-Hydroxymorphinan.