Neurotoxic Effects of Nitrogen Mustard Analogues of Choline

  • E. H. Colhoun
Part of the Advances in Behavioral Biology book series (ABBI, volume 30)


The first synthesis of acetylcholine mustard (AChM) can be attributed to Hanby and Rydon (11), and the toxicology of it and other nitrogen mustard analogues of choline to Anslow et al. (1). Jackson and Hirst (15) modified the synthesis procedure to give higher yield, and showed clearly that the biological activity of AChM was due to formation of the aziridinium ion (Az) isomer in a polar solvent. The framework molecular model of the parent mustard compound, its Az ion isomer and acetylcholine (ACh) is illustrated in Fig. 1. Note the similarity between ACh and the Az ion isomer and in particular the ammonium head. In our laboratory the synthesis technique for the production of AChMAz has, with modifications, been utilized for the synthesis of other mustard analogues (Fig. 2). These compounds are acetylmonoethycholine mustard (AMEChM) and ethoxycholine mustard (EChM). Choline mustard (ChM) and monoethylcholine mustard (MEChM) Az were obtained by alkaline hydrolysis of the acetylated analogues. The aziridinium ion isomers are denoted by the Az suffix.


Medial Septum Nitrogen Mustard Elsevier Scientific Publishing Company Phrenic Nerve Activity Cholinergic Nerve Terminal 
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Copyright information

© Plenum Press, New York 1986

Authors and Affiliations

  • E. H. Colhoun
    • 1
  1. 1.Department of Pharmacology and ToxicologyThe University of Western OntarioLondonCanada

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