HN1 (nitrogen mustard)
|HN1 (nitrogen mustard)|
|Jmol-3D images||Image 1|
|Molar mass||170.08 g mol−1|
|Density||1.0861 g mL−1 (at 20 °C)|
|Melting point||−34 °C (−29 °F; 239 K)|
|Boiling point||85.5 °C (185.9 °F; 358.6 K)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
Bis(2-chloroethyl)ethylamine is the organic compound with the formula C2H5N(CH2CH2Cl)2. Often abbreviated HN1, it is a powerful vesicant and a nitrogen mustard gas used for chemical warfare. HN1 was developed in the 1920s and 1930s to remove warts and later as a military agent. Because of the latter use, it is a Schedule 1 chemical within the Chemical Weapons Convention and therefore use and production is strongly restricted.
It is an oily liquid with a colorless to pale yellow appearance and a faint fishy or musty odor.
Mode of action
Nitrogen mustards react via an initial cyclization to the corresponding aziridinium salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize. The aziridinium ion reacts with water in a slower reaction. At pH 8, the nitrogen mustards are essentially quantitatively converted to the aziridinium ion for subsequent slow reaction with water. In contrast, at pH 4 cyclization and hydrolysis show the classic form of reactions in series.
Brain tumors are hard to treat in part because many antitumor agents which might otherwise be expected to have useful activity are too polar to pass the blood brain barrier effectively and fail to reach the site of the cancer. Nitrogen mustards are alkylating agents which fall into the category of antitumor agents which do not penetrate into the CNS. It is well known that a number of hydantoins pass through the highly lipid capillary membranes and, indeed, a number of CNS depressants possess this structural feature. Combination of a hydantoin moiety to serve as a carrier with a latentiated nitrogen mustard results in spiromustine.
- The Emergency Response Safety and Health Database: NITROGEN MUSTARD HN-1. National Institute for Occupational Safety and Health. Accessed March 19, 2009.
- Peng, G. W.; Marquez, V. E.; Driscoll, J. S. (1975). "Potential central nervous system antitumor agents. Hydantoin derivatives". Journal of Medicinal Chemistry 18 (8): 846–9. doi:10.1021/jm00242a019. PMID 1159704.