Ethylcholine mustard
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H14ClNO | |
| Molar mass | 151.63 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Ethylcholine mustard is a neurotoxic nitrogen mustard that destroys cholinergic neurons.[2][3] It's the hydrolysis product of the HN1 vesicant.[1]
Mechanism of action
Under aqueous condition, ethylcholine mustard forms the highly reactive ethylcholine aziridinium (AF64A) ion. AF64A is transported into cholinergic neurons by the choline transporter. AF64A irreversibly inhibits the choline acetyltransferase and thereby inhibits acetylcholine synthesis. AF64A can also produce cytotoxic effects, leading to cell death.[2][3]
The aziridinium ion can be isolated as picrylsulfonate salt.[1]
- ^ a b c "Chemical Warfare Agents, and Related Chemical Problems, Parts III-VI-Summary Technical Report".
- ^ a b Sandberg, K.; Schnaar, R. L.; McKinney, M.; Hanin, I.; Fisher, A.; Coyle, J. T. (February 1985). "AF64A: An Active Site Directed Irreversible Inhibitor of Choline Acetyltransferase". Journal of Neurochemistry. 44 (2): 439–445. doi:10.1111/j.1471-4159.1985.tb05434.x. PMID 3838098. S2CID 10890459.
- ^ a b Colhoun, E.H.; Rylett, R.J. (January 1986). "Nitrogen mustard analogues of choline: potential for use and misuse". Trends in Pharmacological Sciences. 7: 55–58. doi:10.1016/0165-6147(86)90253-1.
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| Antineoplastic agents |
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| Neurotoxins |
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| Bicyclic phosphates | |
| Cholinergic neurotoxins |
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