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Ethylcholine mustard

From Wikipedia, the free encyclopedia
Ethylcholine mustard
Names
Other names
HN1 chlorohydrin[1]
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H14ClNO/c1-2-8(4-3-7)5-6-9/h9H,2-6H2,1H3
    Key: ODCWAALEHCNIBY-UHFFFAOYSA-N
  • CCN(CCO)CCCl
Properties
C6H14ClNO
Molar mass151.63 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Ethylcholine mustard is a neurotoxicnitrogen mustard that destroyscholinergic neurons.[2][3] It's the hydrolysis product of theHN1vesicant.[1]

Mechanism of action

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Under aqueous condition, ethylcholine mustard forms the highly reactive ethylcholine aziridinium (AF64A) ion. AF64A is transported into cholinergic neurons by thecholine transporter. AF64A irreversibly inhibits thecholine acetyltransferase and thereby inhibitsacetylcholine synthesis. AF64A can also produce cytotoxic effects, leading to cell death.[2][3]

The aziridinium ion can be isolated aspicrylsulfonate salt.[1]

See also

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References

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  1. ^abc"Chemical Warfare Agents, and Related Chemical Problems, Parts III-VI-Summary Technical Report".
  2. ^abSandberg, 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.
  3. ^abColhoun, 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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