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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.
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.
Previous research has shown that sex differences exist in the composition of lateral movements (E. F. Field, I. Q. Whishaw, & S. M. Pellis, 1996, 1997a, 1997b; see also records 1996-06132-009, 1997-05322-015, and 1997-04722-005). An unresolved question is whether sex differences are present in other movements, such as rotation around the longitudinal axis, and whether this difference is dependent on a feminine or masculine skeletomusculature. Female rats (Rattus norvegicus) first rotate their forequarters and then their hindquarters in the same direction. Male rats exhibit rotation of the hindquarters counter to the direction of forequarter rotation. Males with the testicular feminized mutation, who have a feminized skeletomusculature and masculinized central nervous system, are similar to male controls. This study provides evidence that sex differences in movement integration are not restricted to the lateral plane, are not solely due to sex differences in skeletomusculature, and thus are likely mediated by the central nervous system.
Rats protect food by dodging horizontally away from a conspecific. Females and males use different movement and stepping patterns to execute a dodge. An unresolved question is whether exposure to ovarian steroids in females is necessary for the development of the female-typical pattern. Females ovariectomized neonatally and prior to puberty use a combination of male and female tactics. Pregnant females, however, use a female-typical pattern of dodging, suggesting that the patterns used by prepubertal ovariectomized females are not due to their increase in body mass. Thus, the contribution of ovarian steroids to the development of female-typical patterns of behavior needs to be studied further at both a behavioral and neural level with regard to the organization of movement.
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