His choice was made: Curtius embarked upon a career in chemistry, though he remained active as a pianist, singer and composer throughout his life. endobj << Ohmori et al25 investigated the influence of red blood cells on the stability of azide by comparing the stability in the plasma fraction to the red blood cell fraction. /Parent 8 0 R Separation took place by gas chromatography using a temperature gradient. Thatt fell to others, who suggested an isocyanate intermediate might be involved. In line with this, Ohmori et al have suggested that azide is transported from plasma into red blood cells and ultimately destroyed by oxyhemoglobin (O2‐Hb).25 In case 2, the blood sample was collected 3‐4.5 hours after the estimated time of ingestion, thus around the tmax of azide. 26 The isomerization proceeds more conveniently at 140 °C in the presence of iodine. In 1857, Theodor Curtius was born in the Prussian Rhineland city of Duisburg, situated at the confluence of the Rhine and Ruhr rivers. Samples were mixed by vortex‐mixing, centrifuged at 23 100 × g for 5 minutes and snap‐frozen in an ethanol/dry ice bath. Reaction with nitrous acid (HNO2) led to the corresponding acyl azide, and substitution using sodium ethoxide then gave sodium azide (NaN3). /Rotate 0 No carry‐over was observed. >> Alternatively, the acyl azide can be formed by the direct reaction of a carboxylic acid with diphenylphosphoryl azide (DPPA). Ber., 1963, 96, SI (DOI: 10.1002/cber.19630960434), 2 T Curtius, Ber. “Curtius rearrangement rxn” By lh.779 – Own work (CC BY-SA 4.0) via Commons Wikimedia. 18 0 obj /Count 0 Since the accuracy varied for cyanide, accurate determination of the stability of cyanide in biological matrices was not possible. endobj /Contents 65 0 R 11 0 obj /CropBox [0 0 595 842] The invention provides a preparation method of 2-amino-3-nitrobenzoic acid. A validation procedure was followed based on guidelines from the Scientific Working Group for Forensic Toxicology (SWGTOX).20 We used a fit‐for‐purpose strategy and included the calibration model, lower limit of quantitation (LLOQ), limit of detection (LOD), accuracy, precision, carry‐over, cross‐analyte interference, dilution integrity and stability.

These results are in agreement with the results of Ohmori et al25 Azide is stable in human plasma at several conditions (Table 2), except at room temperature and long storage in the freezer (1 year). endobj

1. A temperature gradient was applied to the oven starting at 40°C for 2 minutes rising gradually to 150°C at 13 minutes. Separation of hydrogen cyanide, ethyl isocyanate, propionitrile and some contaminants was necessary for the reliable identification and quantification of cyanide and azide. Accordingly, there is a growing relevance and importance to develop methods for the identification and quantification of azide. /Type /Page << The reaction is closely related to the Curtius rearrangement except that in this reaction the acyl azide is produced by reaction of the carboxylic acid with hydrazoic acid via the protonated carboxylic acid, in a process akin to a Fischer esterification. >> 1 K Freudenberg, Chem. /Rotate 0 What is Hofmann Rearrangement 15 0 obj Several reports found elevated levels of cyanide in blood or plasma after azide ingestion.9, 10, 14, 18, 19 The metabolic pathway and whether the production of cyanide took place in vivo or post‐mortem is unknown. /Resources 58 0 R

Acrobat Distiller 4.05 for Macintosh Summary. Laboratory assessment revealed a combined acidosis with a pH of 6.7 (7.35‐7.45), bicarbonate of 10.8 mmol/L (22‐29 mmol/L), pCO2 of 56 mm Hg (35‐48 mm Hg), a plasma lactate level above the detection limit of 20 mmol/L (0.5‐1.7 mmol/L) and a plasma potassium level of 11.2 mmol/L (3.5‐5.0 mmol/L). endobj This nucleophilic attack yields a primary amine, carbamate, or urea derivatives. In the past few years, the attention for azide as a suicide drug in The Netherlands is raising. /MediaBox [0 0 595 842]

/Type /Page Besides the effects on the cardiovascular system, it causes an enhanced excitatory transmission in the central nervous system after conversion to nitric oxide. Please check your email for instructions on resetting your password. The full text of this article hosted at iucr.org is unavailable due to technical difficulties. %���� This patient (female, 41 years old) was found at home after an alarming farewell e‐mail. /Resources 64 0 R /MediaBox [0 0 595 842] /MediaBox [0 0 595 842] According to the literature, azide is not stable in biological matrices, but the stability data were inconsistent.

A few methods have been described in the literature for the determination of azide in biological matrices,8-17 but not for the combined analysis of azide and cyanide using the same procedure. The sample pretreatment was performed in a fume hood. Moreover, we aimed to apply the method for the measurement of azide and cyanide in biological samples in two lethal cases with suspected azide ingestion. 2007-10-10T03:40:31+09:00 He published the Curtius rearrangement in 1890/1894 and also discovered diazoacetic acid, hydrazine and hydrazoic acid. /Count 8 /Resources 62 0 R

/Resources 48 0 R Lett., 2005, 7, 4107-4110. The Curtius rearrangement (or Curtius reaction or Curtius degradation), first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas. /CropBox [0 0 595 842] Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, The ratio ethyl isocyanate/propionitrile (A) and area of ethyl isocyanate and propionitrile (B) at several time‐points after addition of propionic anhydride, By continuing to browse this site, you agree to its use of cookies as described in our, orcid.org/https://orcid.org/0000-0002-0300-8281, I have read and accept the Wiley Online Library Terms and Conditions of Use, Evaluation of mutagenicity and other adverse effects of occupational exposure to sodium azide, Studies of the effect of sodium azide on microbic growth and respiration, Comparison of hypotensive action of sodium azide in normotensive and hypertensive patients, Human health effects of sodium azide exposure: a literature review and analysis, Sodium azide [MAK value documentation, 2003], Acute neurotoxicity of sodium azide and nitric oxide, Facile derivatization of azide ions using click chemistry for their sensitive detection with LC‐MS, Convenient headspace gas chromatographic determination of azide in blood and plasma, Analytical findings in a suicide involving sodium azide, Detection of azide in forensic samples by capillary electrophoresis, Determination of sodium azide in the presence of proteins by high‐performance liquid chromatography, Determining sodium azide concentration in blood by ion chromatography, Application of high‐performance liquid chromatography to a fatality involving azide, Determination of azide in blood and urine by gas chromatography‐mass spectrometry, Application of a new analytical method using gas chromatography and gas chromatography–mass spectrometry for the azide ion to human blood and urine samples of an actual case, Liquid chromatographic determination of azide as the 3,5‐dinitrobenzoyl derivative, Suicidal sodium azide intoxication: an analytical challenge based on a rare case, Scientific working group for forensic toxicology (SWGTOX) standard practices for method validation in forensic toxicology, A case of survival following high‐dose sodium azide poisoning, Cyanide: hydrogen cyanide, inorganic cyanide salts, and nitriles, Development and validation of a liquid chromatography‐tandem mass spectrometry analytical method for the therapeutic drug monitoring of eight novel anticancer drugs, Stability of cyanide in cadavers and in postmortem stored tissue specimens: a review, High distribution of azide in blood investigated in vivo, and its stability in blood investigated in vitro, [Suicidal intoxication with sodium azide–a case report]. << /CropBox [0 0 595 842] 1. endobj Chem., 1930, 125, 1 (DOI: 10.1002/prac.19301250101), 8 G Schroeter, Ber. Chem. /Type /Page /Rotate 0 6 0 obj



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