PhD Scientific Days 2023

Budapest, 22-23 June 2023

Pharmaceutical Sciences - Posters F

Synthesis and characterization of N-aminoalkyl-morphine structured haptens

Balázs Simon, Sándor Hosztafi
Department of Pharmaceutical Chemistry/Semmelweis University, Budapest
Department of Pharmaceutical Chemistry/Semmelweis University, Budapest

Text of the abstract

Abuse of drugs belonging to the opioid class is an ever-growing problem of our society, and the available therapy for opioid abuse has a limited scope. Vaccines against drugs of abuse could be a big step forward in this regard, but for this use, these so-called hapten molecules have to be chemically modified, and then they need to be conjugated with an already immunogen carrier macromolecule.
In our research we aimed to synthetise molecules with an N-aminoalkyl-morphinan structure from a N-ciano-alkyl structured derivatives using different reducing agents, and characterizing them using different spectroscopy methods.
Common methods of synthetic organic chemistry were used. We used different nor-opiates as starting materials, and reacted them with acrylonitrile and bromoacetonitrile to get the cyanomethyl and cyanoethyl derivatives. These compounds were reacted with different reducing agents, such as lithium aluminium hydride, sodium borohydride (in presence of different cobalt salts), and sodium bis(2-methoxyethoxy)aluminium dihydride, and were characterized with NMR and IR spectroscopy.
The work is still ongoing, so far, four different aminoalkyl compounds were synthetised, two of them with the use of lithium aluminium hydride, one with sodium borohydride, and one with the sodium bis(2-methoxyethoxy)aluminium dihydride.
The ongoing work is promising, especially the usage of lithium aluminium hydride in different solvent mixtures, but more reactions are needed to fully understand the limits of this method.
Funding: No external funding was received.
E-mail adress:
Semmelweis University
Supervisor: Dr. Sándor Hosztafi
I would like to present this as a poster.