The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Spontaneous autoxidation of dopamine
Abstract
A detailed kinetic study has been carried out of the reaction of dopamine, 2-(3,4-dihydroxyphenyl)ethylamine, with dioxygen over the pH range 7–9 where it reacts spontaneously without the necessity of metal ion catalysis. The reaction was found to be accurately first-order in [O2] and in [dopamine] and first-order in [H+]–1 and, furthermore, stoichiometric amounts of H2O2 were shown to be produced. The other product of oxidation is, initially, the pink dopaminochrome which, however, is not stable and reacts further (without the consumption of dioxygen) to form the insoluble polymeric material known as ‘melanine’. The rate-determining step is assumed to be hydrogen atom abstraction from the monodeprotonated species by O2(as with many other catecholamines, dopamine is stable towards oxidation in acidic media in the complete absence of metal ions) with a second-order rate constant of k1= 0.47 ± 0.05 dm3 mol–1 s–1 at 25 °C in a solution of ionic strength 0.1 mol–1 dm–3(KCl).
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Citations
Cites
Oxidative Pathways for Catecholamines in the Genesis of Neuromelanin and Cytotoxic Quinones
GRAHAM, D. G. (1978) · Molecular Pharmacology · doi:10.1016/s0026-895x(25)13535-9 · Cited by 1,126
Cited by
Characterization of Polydopamine Thin Films Deposited at Short Times by Autoxidation of Dopamine
Zangmeister, R. A., Morris, T. A., & Tarlov, M. J. (2013) · Langmuir · doi:10.1021/la400587j · Cited by 983
Catechols as versatile platforms in polymer chemistry
Faure, E., Falentin-Daudré, C., Jérôme, C., Lyskawa, J., Fournier, D., Woisel, P., & Detrembleur, C. (2013) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2012.06.004 · Cited by 616
Boronic Acid-Based Hydrogels Undergo Self-Healing at Neutral and Acidic pH
Deng, C. C., Brooks, W. L. A., Abboud, K. A., & Sumerlin, B. S. (2015) · ACS Macro Letters · doi:10.1021/acsmacrolett.5b00018 · Cited by 438
Kruss, S., Landry, M. P., Vander Ende, E., Lima, B. M. A., Reuel, N. F., Zhang, J., Nelson, J., Mu, B., Hilmer, A., & Strano, M. (2014) · Journal of the American Chemical Society · doi:10.1021/ja410433b · Cited by 391
Polydopamine Spheres as Active Templates for Convenient Synthesis of Various Nanostructures
Yan, J., Yang, L., Lin, M., Ma, J., Lu, X., & Lee, P. S. (2013) · Small · doi:10.1002/smll.201201064 · Cited by 355
Metadata
- Authors
- Herlinger, E., Jameson, R. F., & Linert, W.
- Venue
- Journal of the Chemical Society, Perkin Transactions 2
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 1995
- Issue
- 2
- Pages
- 259
- ISSN
- 0300-9580 (ISSN-L)
- 1364-5471
- OpenAlex
- W2060887289
- Cited by
- 227
- References
- 1
- FWCI
- 1.51
- Type
- journal article
- Language
- en
- Open access
- closed
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- Herlinger, E., Jameson, R. F., & Linert, W. (1995). Spontaneous autoxidation of dopamine. Journal of the Chemical Society, Perkin Transactions 2. https://doi.org/10.1039/p29950000259
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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