Ethylcholine mustard

Ethylcholine mustard

Names
Other names HN1 chlorohydrin[1]
Identifiers
CAS Number	4669-20-9
3D model (JSmol)	Interactive image
ChemSpider	172807
PubChem CID	199656
CompTox Dashboard (EPA)	DTXSID70196904
InChI InChI=1S/C6H14ClNO/c1-2-8(4-3-7)5-6-9/h9H,2-6H2,1H3 Key: ODCWAALEHCNIBY-UHFFFAOYSA-N
SMILES CCN(CCO)CCCl
Properties
Chemical formula	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). Infobox references

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

• HN1 (nitrogen mustard)

References

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