Application of Electronic Spectroscopy and Quantum-Chemical Modeling for Analysis of Products of Autoxidation of Adrenaline

Guzov, E. A.; Казин, В. Н.; Moshareva, V. A.; Жукова, А. А.

doi:10.1007/s10812-019-00766-9

Cited by 6 publications

(7 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It has been reported that adrenaline's chirality and amino moiety trigger sensitivity to degradation [32] by oxidation (Figures 2a and 3), autooxidation, racemisation, and excipient interaction [28]. Oxidation and racemisation are known to proliferate in alkaline solutions [44], upon exposure to light and temperature changes [45], but they become retarded under acidic conditions, as confirmed by…”

Section: Stability Investigationmentioning

confidence: 72%

“…Under acidic conditions, the UV spectra of adrenaline revealed distinctive peaks at 280 nm and 221 nm, and the CD spectra exhibited a negative ellipticity signal at 230 nm. These arise from the phenol chromophore electronic transitions π → π*, which are indicative of (−)-adrenaline [44]. After 24 h of exposure, there were no significant differences in UV (p = 0.96) and CD (p = 0.23) when compared to the control and no visible changes; the solutions remained clear and colourless with no precipitation or turbidity (Supplementary SI 4).…”

Section: Stability Investigationmentioning

confidence: 97%

“…However, after exposure to alkaline conditions for 24 h, the UV spectra of adrenaline exhibited a bathochromic and hyperchromic shift in λmax from 280 nm to 300 nm. This shift is indicative of the adrenaline multistate transitions, where adrenaline oxidises into various degradative o-quinone structures arising from the charge transfer between the benzene chromophore and oxygen [44] ( Figure 2b).…”

Section: Stability Investigationmentioning

confidence: 99%

“…The consecutive rapid oxidation and auto-oxidation of these structures subsequently forms coloured yet pharmacologically inactive indole derivatives [32]. The major indole-derivative degradant adrenochrome sets up a redox cycling process advancing oxidation and auto-oxidation [44]. Under acidic conditions, cyclisation is prevented.…”

Section: Stability Investigationmentioning

confidence: 99%

See 3 more Smart Citations

An Evaluation of the Drone Delivery of Adrenaline Auto-Injectors for Anaphylaxis: Pharmacists’ Perceptions, Acceptance, and Concerns

Beck

Bui

Davies

et al. 2020

Drones

View full text Add to dashboard Cite

Anaphylaxis is a life-threatening condition where delays in medical treatment can be fatal. Such situations would benefit from the drone delivery of an adrenaline auto-injector such as EpiPen®. This study evaluates the potential risk, reward, and impact of drone transportation on the stability of adrenaline during episodes of anaphylaxis. Further, this study examines pharmacists’ perceptions on drone delivery—pharmacists approved the use of drones to deliver EpiPen® during emergencies but had concerns with drone safety and supply chain security. Laboratory simulated onboard drone conditions reflected typical missions. In these experiments, in vitro model and pharmaceutical equivalent formulations were subjected independently to 30 min vibrations at 5, 8.43, and 13.33 Hz, and temperature storage at 4, 25, 40, and 65 °C for 0, 0.5, 3, and 24 h. The chiral composition (an indicator of chemical purity that relates to molecular structure) and concentration of these adrenaline formulations were determined using ultraviolet (UV) and circular dichroism spectroscopy (CD). Adrenaline intrinsic stability was also explored by edge-of-failure experimentation to signpost the uppermost limits for safe transportation. During drone flight with EpiPen®, the temperature and vibration g-force were 10.7 °C and 1.8 g, respectively. No adverse impact on adrenaline was observed during drone flight and laboratory-simulated conditions shown by conformation to the British Pharmacopeia standards (p > 0.05 for CD and UV). This study showed that drone delivery of EpiPen® is feasible. There are more than 15,000 community pharmacies and ≈9000 GP surgeries spanning the UK, which are likely to provide achievable ranges and distances for the direct drone delivery of EpiPen®. The authors recommend that when designing future missions, in addition to medicine stability testing that models the stresses imposed by drone flight, one must conduct a perceptions survey on the relevant group of medical professionals, because their insights, acceptance, and concerns are extremely valuable for the design and evaluation of the mission.

show abstract

Section: Stability Investigationmentioning

confidence: 72%

Section: Stability Investigationmentioning

confidence: 97%

Section: Stability Investigationmentioning

confidence: 99%

Section: Stability Investigationmentioning

confidence: 99%

See 2 more Smart Citations

An Evaluation of the Drone Delivery of Adrenaline Auto-Injectors for Anaphylaxis: Pharmacists’ Perceptions, Acceptance, and Concerns

Beck

Bui

Davies

et al. 2020

Drones

View full text Add to dashboard Cite

show abstract

“…The kinetics of adrenaline autoxidation were studied using the rate of consumption (W) at T = 310 ± 0.1 K in carbonate buffer (pH = 10.40-10.70) using the method of electron spectroscopy on a Perkin Elmer Lambda 35 spectrophotometer (USA) similarly to [29].…”

Section: Methodsmentioning

confidence: 99%

Influence of a Constant Magnetic Field on the Mechanism of Adrenaline Oxidation

et al. 2022

View full text Add to dashboard Cite

In order to establish the role of the magnetic effect in the key stages of the autoxidation and initiated oxidation radical-chain reactions, the experimental data and kinetic analysis of the influence of a magnetic field on the oxidative transformations of adrenaline are presented in this work. In the case of autoxidation, the process is being controlled by the rate of adrenaline consumption in the gross process of quinoid oxidation. The analysis of the obtained results is estimative and is based on the assumption of the leading role of superoxide radical during the autoxidation. Superoxide radical concentration increases with the increase in the applied magnetic field strength, which leads to the decrease in the rate of initiation of the quinoid process. In the case of initiated oxidation, the results obtained are based on the known radical-chain mechanism, and they were interpreted using the theory of radical pairs. The observed magnetic effect is explained by the influence of a constant magnetic field on the mechanism of chain termination of radical-chain oxidation and/or initiation of the autoxidation process.

show abstract