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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
Antihypertensive Drugs: Vasodilators01:23

Antihypertensive Drugs: Vasodilators

Vasodilators, primarily affecting the smooth muscles within arterial and venous walls, are commonly used for hypertension treatment. Medications such as minoxidil and hydralazine primarily target arteries and arterioles, while sodium nitroprusside acts on arterioles and venules. Minoxidil, functioning as a prodrug, is metabolized by hepatic sulfotransferase into its active form, minoxidil sulfate, after oral administration. This metabolite binds to the sulfonylurea receptor (SUR) component of...

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Novel Whole-tissue Quantitative Assay of Nitric Oxide Levels in Drosophila Neuroinflammatory Response
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Decay of nitroprusside. I: In vitro.

C J Vesey1, M Stringer, P V Cole

  • 1Anaesthetics Laboratory, St Bartholomew's Hospital, West Smithfield, London.

British Journal of Anaesthesia
|June 1, 1990
PubMed
Summary

Nitroprusside (SNP) decomposition in blood generates cyanide (HCN), contrary to prior beliefs. This reaction is temperature, pH, and time-dependent, occurring significantly within blood but not during standard assays.

Area of Science:

  • Pharmacology
  • Clinical Chemistry
  • Toxicology

Background:

  • Intravascular decomposition of sodium nitroprusside (SNP) was previously attributed to photolysis and assay artifacts, suggesting safe infusion if light is excluded.
  • Concerns existed regarding the generation of cyanide (HCN) from SNP in vivo, impacting its safe clinical use.

Purpose of the Study:

  • To investigate the true mechanism and conditions for cyanide (HCN) generation from sodium nitroprusside (SNP) in blood.
  • To determine if SNP decomposition occurs in blood independently of light exposure or assay artifacts.
  • To quantify the rate and factors influencing HCN release from SNP in a blood matrix.

Main Methods:

  • Incubation of SNP with blood and plasma under varying conditions (temperature, pH, time).

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Platelet-based Detection of Nitric Oxide in Blood by Measuring VASP Phosphorylation
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  • Measurement of HCN generated using a validated analytical method.
  • UV spectrophotometry was employed to assess SNP concentration and distribution in plasma.

    • Main Results:

    • HCN generation from SNP did not occur during standard analytical procedures.
    • Significant HCN formation was observed exclusively after SNP incubation with blood.
    • HCN release was dependent on temperature, pH (optimal around 7.5 in plasma), and incubation time, with 50% release at 37°C in blood occurring in 26.6 minutes and >90% yield within 2 hours.
    • UV analysis indicated SNP primarily resides in plasma at clinically relevant concentrations.

    Conclusions:

    • Sodium nitroprusside (SNP) decomposition with cyanide (HCN) release is an intrinsic reaction with blood components, not an artifact of light or assay.
    • The rate of HCN release is significantly influenced by physiological conditions within the blood.
    • Understanding these decomposition kinetics is crucial for safe SNP administration and managing potential cyanide toxicity.