106262-09-3Relevant academic research and scientific papers
Synthetic method of morphine derivative and applications
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Paragraph 0073-0074, (2018/05/07)
The invention discloses a synthetic method of a morphine derivative. The method employs morphine as an initial raw material, and selective protection and glycosylation are carried out in order to obtain a target product. The HPLC purity of M3G obtained by the synthetic method reaches 99.8%, and the M3G can be used as a reference substance or a standard substance for researching quality of relatedproducts.
Preparation of benzoate esters of morphine and its derivatives
Beni, Szabolcs,Toth, Gergo,Noszal, Bela,Hosztafi, Sandor
, p. 1431 - 1440,10 (2020/08/20)
Sustained analgesia is crucial for patients suffering from long-acting pain. Ester derivatives of morphine could enhance the lipophilicity of morphine; consequently its transdermal delivery as well as its duration of action are also increased. Therefore, twenty-one 3-O-, 6-O-, and 14-Obenzoate esters of morphine and their derivatives were synthesized in order to elaborate different synthetic methods suitable for esterification of these widely used compounds. Schotten-Baumann reaction was applied with sodium hydrogen carbonate, triethylamine, or pyridine in methylene chloride or 1,2-dichloroethane as solvents. The presence of 4-dimethylaminopyridine catalyst was also successfully utilized mainly in the case of tertiary alcohols. A novel synthesis of dihydromorphine via diacetyl morphine free of by-products is also presented. Structures of all synthesized compounds were elucidated by 1H nuclear magnetic resonance (NMR), 13CNMR, high-resolution mass spectrometry (HRMS), and electron ionizationmass spectrometry (EI-MS). The log D (pH 7.4) values of the synthesized compounds were determined by a reversed-phase high-performance liquid chromatography (HPLC)-MS-based method, and calculated hydrolysis rate constants are also provided. The synthesized benzoate esters are potential prodrugs of the parent morphine with enhanced lipophilicity, derivatives which can also be used in transdermal drug delivery as prospective long-acting narcotic analgesics.
Methods of synthesis of morphinans
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Page/Page column 7, (2009/12/28)
The disclosure describes morphinan compounds and methods for their synthesis. Preferred methods according to the disclosure allow for large-scale preparation of diastereomerically enriched morphinans. Preferred methods according to the disclosure may also
Aminimides as potential CNS-acting agents. III. Design, synthesis, and receptor binding of aminimide analogues of dopamine, serotonin, morphine, and nicotine
Capuano, Ben,Crosby, Ian T.,Lloyd, Edward J.,Neve, Juliette E.,Taylor, David A.
, p. 422 - 431 (2008/12/20)
A series of aminimide derivatives of centrally acting agents, namely dopamine, serotonin, morphine and nicotine, were designed on the basis of the physicochemical properties of the aminimide functional group and synthesized to investigate their central nervous system (CNS) receptor affinity. The target compounds were readily prepared from an appropriate tertiary amine by N-acylation of a hydrazinium salt intermediate using acetic anhydride or acetyl chloride. The aminimides were tested for in vitro affinity at the dopaminergic D4, serotonergic 5-HT2A, opiate (?, ?, and non-selective) and nicotinic acetylcholine receptors and were found to possess mixed affinities for the aforementioned receptor systems. CSIRO 2008.
