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{{Chembox |
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| Name = Ethylcholine mustard |
| Name = Ethylcholine mustard |
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| OtherNames = [[HN1 (nitrogen mustard)|HN1]] chlorohydrin |
| OtherNames = [[HN1 (nitrogen mustard)|HN1]] chlorohydrin<ref name="PB158507">{{cite web |title=Chemical Warfare Agents, and Related Chemical Problems, Parts III-VI-Summary Technical Report. |url=https://ntrl.ntis.gov/NTRL/dashboard/searchResults/titleDetail/PB158507.xhtml}}</ref> |
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| ImageFile = Ethylcholine mustard.png |
| ImageFile = Ethylcholine mustard.png |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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| C=6|H=14|Cl=1|N=2|O=1 |
| C=6|H=14|Cl=1|N=2|O=1 |
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| Section3 = {{Chembox Hazards |
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| LD50 = |
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'''Ethylcholine mustard''' is a neurotoxic [[nitrogen mustard]] that destroys [[cholinergic neuron]]s. It’s the hydrolysis product of the [[HN1 (nitrogen mustard)|HN1]] [[vesicant]]. |
'''Ethylcholine mustard''' is a neurotoxic [[nitrogen mustard]] that destroys [[cholinergic neuron]]s.<ref name="ref1">{{cite journal |last1=Sandberg |first1=K. |last2=Schnaar |first2=R. L. |last3=McKinney |first3=M. |last4=Hanin |first4=I. |last5=Fisher |first5=A. |last6=Coyle |first6=J. T. |title=AF64A: An Active Site Directed Irreversible Inhibitor of Choline Acetyltransferase |journal=Journal of Neurochemistry |date=February 1985 |volume=44 |issue=2 |pages=439–445 |doi=10.1111/j.1471-4159.1985.tb05434.x}}</ref><ref name="ref2">{{cite journal |last1=Colhoun |first1=E.H. |last2=Rylett |first2=R.J. |title=Nitrogen mustard analogues of choline: potential for use and misuse |journal=Trends in Pharmacological Sciences |date=January 1986 |volume=7 |pages=55–58 |doi=10.1016/0165-6147(86)90253-1}}</ref> It’s the hydrolysis product of the [[HN1 (nitrogen mustard)|HN1]] [[vesicant]].<ref name="PB158507" /> |
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==Mechanism of action== |
==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 the [[choline transporter]]. AF64A irreversibly inhibits the [[choline acetyltransferase]] and thereby inhibits [[acetylcholine]] synthesis. AF64A can also produce cytotoxic effects, leading to cell death. |
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.<ref name="ref1" /><ref name="ref2" /> |
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The aziridinium ion can be isolated as [[picrylsulfonate]] salt. |
The aziridinium ion can be isolated as [[picrylsulfonate]] salt.<ref name="PB158507" /> |
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==See also== |
==See also== |
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Revision as of 15:35, 24 December 2023
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3D model (JSmol)
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| Properties | |
| C6H14ClN2O | |
| Molar mass | 165.64 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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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]
See also
References
- ^ 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.
- ^ 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.