Separation and Quantitation of Methenamine in Urine by Ion-Pair Extraction

This is an update of a previous chapter. It presents an evaluation of the toxicological potential of a number of aliphatic and aromatic nitrogen compounds, with information on their use, production, and exposure scenarios. These compounds were originally selected on the basis of their use in industry. In general, there has been little new information published in the literature that has significantly altered the previous profile of each compound. The three‐membered ring compounds discussed are ethyleneimine, propylenenimine, and triethylenemelamine. They are alkylating agents and have toxicological properties similar to nitrogen mustards. Six nitrogen mustards and their hydrochlorides are discussed as a group of chemicals. Furthermore, data on representatives of five‐membered ring nitrogen compounds (pyrrolidine, N ‐methyl‐2‐pyrrolidone) and of six‐membered ring compounds (piperidine, piperazine, morpholine, and hexamethylenetetramine) are included. Captan, captafol, and folpet—three N ‐sulfenyl phthalimide fungicides—and benomyl, carbendazim, and thiophanate‐methyl—benzimidazole fungicides—are evaluated as separate groups. Data on 1‐ H ‐benzotriazol are also included in this chapter. The subchapter of each compound or group of compounds includes the physical and chemical properties, information as to use and production, data on the toxicological potential, and standards, regulations, or guidelines of exposure. In addition, data on the environmental impact of each compound or group of compounds are presented and evaluated.

Selected Aliphatic and Aromatic Nitrogen Compounds

Ziegler‐Skylakakis

2023

Aliphatic and Aromatic Nitrogen Compounds

Trochimowicz¹,

Kennedy²,

Krivanek³

2001

This chapter covers both aliphatic and aromatic compounds that contain one or more nitrogen atoms in their structures. Only a small number of the nitrogen‐containing compounds that could be considered will be reviewed here based mainly on their uses in industry. Three‐membered rings discussed are ethyleneimine, propyleneimine, and one polyfunctional derivative, triethylenemelamine. Toxicologists, chemists, and biologists have always been interested in ethylenimine and its derivatives because they are reactive, are useful at relatively low doses, and are moderately to highly toxic. Ethylenimines are classic alkylating agents and have toxicological effects similar to nitrogen mustards. Monofunctional derivatives of ethylenimine are less potent in producing the characteristic toxicity of the group than the derivatives that have two or more ethylenimine groups. Finally, polymers of ethylenimine and its derivatives have shown a relatively low order of toxicity. Six simple nitrogen mustards (β‐chloroethylamines) are also covered in this chapter. They are all tertiary amines in which the halogen atom and the amine portion have reactivities similar to the alkyl halides and alkyl amines. They have no significant industrial uses in the United States, but they are used in medicine as “antineoplastic agents” and in treating some nonmalignant diseases. Representative nitrogen‐containing chemicals that have five‐membered rings (pyrrolidine, NMP) and six‐membered rings (piperidine, piperazine, morpholine, and HMTA) are also discussed in this chapter in some detail.

Aliphatic and Aromatic Nitrogen Compounds

Kennedy¹

2012

This chapter covers both aliphatic and aromatic compounds that contain one or more nitrogen atoms in their structures. Only a small number of the nitrogen‐containing compounds that could be considered will be reviewed here mainly based on their uses in industry. This is an update of a previous chapter and for each chemical, the first sentence will tell the reader whether there has been significant new information published in the literature and included or whether there has been little or no new information available for update and inclusion. Three‐membered rings discussed are ethyleneimine, propyleneimine, and, one polyfunctional derivative, triethylenemelamine. Toxicologists, chemists, and biologists have always been interested in ethyleneimine and its derivatives because they are reactive, are useful at relatively low doses, and are moderately to highly toxic. Ethyleneimines are classic alkylating agents and have toxicological effects similar to nitrogen mustards. Monofunctional derivatives of ethyleneimine are less potent in producing the characteristic toxicity of the group than the derivatives that have two or more ethyleneimine groups. Finally, polymers of ethyleneimine and its derivatives have shown a relatively low order of toxicity. Six simple nitrogen mustards (β‐chloroethylamines) are also covered in this chapter. They are all tertiary amines in which the halogen atom and the amine portion have reactivities similar to the alkyl halides and alkyl amines. They have no significant industrial uses in the United States, but they are used in medicine as “antineoplastic agents” and in treating some nonmalignant diseases. Representative nitrogen‐containing chemicals that have five‐membered rings (pyrrolidine, N ‐methyl‐2‐pyrrolidinone) and six‐membered rings (piperidine, piperazine, morpholine, and hexamethylenetetramine) are also discussed in this chapter in some detail. Several representative aromatic nitrogen compounds are covered—pyrrole, aminotriazole, N ‐sulfenyl phthalimide fungicides, benzimidazole fungicides, and 1‐ H ‐benzotriazole. The data presented for compounds of this class that are used in agriculture include toxicology studies that have been published in the open literature as well as those available through company files to support governmental registration. In some cases, the high toxicity of the agent has been considered and is the reason for its inclusion here, rather than usage volume or industrial importance. Further, very little pharmacological information is presented because this is adequately covered in the pharmacological literature. We have tried to minimize hypotheses regarding the mechanism of action not because it is unimportant, but because the biochemistries are often very detailed, are almost always fairly speculative, and are presented comprehensively in other texts. Likewise, we resisted the temptation to employ structure–activity relationships because, although the database is very thorough for some chemicals, it did not contain enough analogous chemicals with known, comparable toxicity profiles.