Are nitrate esters likely to produce peroxy containing species?

László L. Torday, Svend J. Knak Jensen, I. Csizmadia

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

One of the most limiting factors in the use of organic nitrates as vasodilators in medicine is the development of nitrate tolerance. The chemistry leading to nitrate tolerance is not fully understood, newly formed reactive oxygen species, such as the peroxynitrite anion, have been suggested to play a central role. To elucidate the steps of the development of nitrate tolerance the aqueous phase interconversions of the isomeric methyl esters of peroxynitrous acid and nitric acid are studied computationally by quantum mechanical geometry optimizations and statistical mechanical methods. These calculations show that methyl nitrate is more stable than methyl peroxynitrite by about 134 kJ/mol. The energy of the transition state connecting the isomers is about 296 kJ/mol higher than that of methyl nitrate. This finding suggests that the direct isomerization of methyl nitrate to methyl peroxynitrite is of no importance at physiological conditions.

Original languageEnglish
Pages (from-to)139-146
Number of pages8
JournalMedicinal Chemistry Research
Volume12
Issue number3
Publication statusPublished - 2003

Fingerprint

Nitrates
Esters
Peroxynitrous Acid
Nitric Acid
Isomerization
Vasodilator Agents
Isomers
Medicine
Anions
Reactive Oxygen Species
Geometry
methyl nitrate
methyl peroxynitrite

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry

Cite this

Are nitrate esters likely to produce peroxy containing species? / Torday, László L.; Knak Jensen, Svend J.; Csizmadia, I.

In: Medicinal Chemistry Research, Vol. 12, No. 3, 2003, p. 139-146.

Research output: Contribution to journalArticle

Torday, László L. ; Knak Jensen, Svend J. ; Csizmadia, I. / Are nitrate esters likely to produce peroxy containing species?. In: Medicinal Chemistry Research. 2003 ; Vol. 12, No. 3. pp. 139-146.
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