58772-72-8Relevant academic research and scientific papers
Preparation and analgesic activity of 3,6 diacetylnormorphine and 6 acetylnormorphine
Rice,Jacobson
, p. 1033 - 1035 (1975)
3,6 Diacetylnormorphine (norheroin) and 6 acetylnormorphine have been prepared in excellent yield through the 3,N bis (tert butoxycarbonyl) derivative of normorphine via acetylation and selective removal of protecting groups. This general procedure would be applicable to the preparation of various 3,6 diesters or 6 monoesters of normorphine. The analgesic potency of norheroin was found to be the same as that of 6 acetylnormorphine, about 0.05 that of heroin. The onset, peak, and duration of action of these compounds were nearly identical and comparable with morphine.
Synthesis of N-demethyl-N-substituted dihydroisomorphine and dihydroisocodeine derivatives
Hosztafi,Simon,Makleit
, p. 1673 - 1682 (1992)
Several new N-demethyl-N-alkyl derivatives (1p, 1r, 1s, 1m, 1n and 1o) of dihydroisomorphine and dihydroisocodeine, and N-demethyl-N-cyclopropylmethylisocodeine (2g) have been prepared. The presented synthetic procedure allows a convenient access to a series of structurally related, stereochemically homogeneous substances for studies of the agonist/antagonist properties.
A chemically contiguous hapten approach for a heroin-fentanyl vaccine
Natori, Yoshihiro,Hwang, Candy S.,Lin, Lucy,Smith, Lauren C.,Zhou, Bin,Janda, Kim D.
supporting information, p. 1020 - 1031 (2019/06/08)
Background: Increased death due to the opioid epidemic in the United States has necessitated the development of new strategies to treat addiction. Monoclonal antibodies and antidrug vaccines provide a tool that both aids addiction management and reduces the potential for overdose. Dual drug vaccines formulated by successive conjugation or by mixture have certain drawbacks. The current study examines an approach for combatting the dangers of fentanyl-laced heroin, by using a hapten with one epitope that has domains for both fentanyl and heroin. Results: We evaluated a series of nine vaccines developed from chemically contiguous haptens composed of both heroin- and fentanyl-like domains. Analysis of the results obtained by SPR and ELISA revealed trends in antibody affinity and titers for heroin and fentanyl based on epitope size and linker location. In antinociception studies, the best performing vaccines offered comparable protection against heroin as our benchmark heroin vaccine, but exhibited attenuated protection against fentanyl compared to our fentanyl vaccine. Conclusion: After thorough investigation of this strategy, we have identified key considerations for the development of a chemically contiguous heroin-fentanyl vaccine. Importantly, this is the first report of such a strategy in the opioid-drug-vaccine field.
Development of a Clinically Viable Heroin Vaccine
Bremer, Paul T.,Schlosburg, Joel E.,Banks, Matthew L.,Steele, Floyd. F.,Zhou, Bin,Poklis, Justin L.,Janda, Kim D.
, p. 8601 - 8611 (2017/07/06)
Heroin is a highly abused opioid and incurs a significant detriment to society worldwide. In an effort to expand the limited pharmacotherapy options for opioid use disorders, a heroin conjugate vaccine was developed through comprehensive evaluation of hap
6-ACETYLMORPHINE ANALOGS, AND METHODS FOR THEIR SYNTHESIS AND USE
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Paragraph 00111; 00151, (2014/10/04)
The present invention relates to novel 6-acetylmorphine analogs, and methods for their synthesis and use. Such analogs are designed to provide a convenient linkage chemistry for coupling under mild conditions to a suitable group on a target protein, polypeptide, solid phase or detectable label.
