Half-mustard

Lee, M. and Garbiras, B.J., Efficient synthesis of benzoic acid half mustards, Synth. Commun. 24, 3129-3134, 1994. 

Fig. 7. Transformation of 2-chloroethylethyl sulfide (half-mustard) into 2-hydroxyethylethyl sulfide by alkali or into 2-chloroethylethyl sulfoxide by hypochlorite...

Kurihara T, Nojima K, Sakagami H, Motohashi N, Molnar J (1999) Electronic structure and cytotoxic activity of half-mustard type phenothiazines by MM3 and PM3 methods. Anticancer Res 19 3895-3899... 

Varma, S.D., Devamanoharan, P.S., Ali, A.H., Henein, M., Petrali, J., Brozetti, J., Lehnert, E. (1998a). Comeal damage by half mustard (2-chloroethyl ethyl sulfide, CEES) in vitro preventive studies a histologic and electron microscopic evaluation. J. Ocul. Pharmacol. Ther. 14 413-21. 

McClintock, S.D., Till, G.O., Smith, M.G., Ward, P.A. (2002). Protection from half-mustard-gas-induced acute lung injury in the rat. J. Appl. Toxicol. 22 257-62. 

SYNS CHLOROpiMETHYLAMINO)ETHANE p-CHLOROETHYLDIMETHYLAMINE (2-CHLORO-ETHYL)DIMETHYLAMINE DIMETHYLAMINOETHYL CHLORIDE p-(DIMETHYLAMINO)ETHYL CHLORIDE 2-DMETHYLAIVnNOETHYLCHLORIDE DIMETH-YL(2-CHLOROETHYL)AMINE HN 1 NITROGEN HALF MUSTARD... 

Figure 3.17 Cyclohexane droplets in water are stabilized by a surfactant (CTAB SDS) and a cosurfactant (dodecanol). The resulting microemulsion is very efficient in the oxidative destruction of half mustard (R2S = EtSCH2CH2Cl) by sodium hypochlorite. ...

Some phenothiazines, the so-called half-mustard type, stimulated T-cell blast formation, presented a natural killer cell activity, via possibly the activation of monocytes and macrophages, and an antibody-dependent cellular cytotoxicity of human peripheral blood mononuclear cells, and also showed cytotoxicity against several human cancer cell lines. These phenothiazines also might induce an in vivo antimicrobial activity by possibly their host-mediated immuno-potentiation [146]. Phenothiazines did not demonstrate any apparent mutagenic activity, but they were rather antimutagenic. These data suggest the possible applicability of half-mustard type phenothiazines and benzo[a]phenothiazines to cancer chemotherapy. 

F. Inscore and S. Farquharson, Surface-enhanced Raman Spectroscopic characterization of sulfur mustard, half-mustard, their hydrolysis products and related mono-sulfides, J. Raman Spectros. (in preparation). 

Menger and Elrington found these principles to be valid too in the case of mustard detoxification [34]. Their oil-in-water (o/w)-type microemulsion was formed by 3 wt % cyclohexane, 82 wt % water, 5 wt % SDS, and 10 wt % butanol. The addition of O.lSmL half-mustard, a nontoxic substance and chemically similar to mustard, and 5 wt % aqueous hypochlorite to 15 mL microemulsion initiates a fast reaction to sulfoxides, which was finished within 15 s. Figure 14.7 shows the proposed mechanism for the oxidation. An alkyl hypochlorite is assumed to be formed at the oil-water interface and the oxidation of half-mustard to sulfoxide only takes place close to the interfacial region or inside the oil phase. This interfacial reaction is orders of tnagnimde faster than a sulfide oxidation in a two-phase phase transfer catalysis system [41],... 

FIGURE 14.7 Scheme of the mechanism for the oxidation of half-mustard. Alkyl hypochlorite formation at the oil-water interface enables an oxidation close to the interface or inside the oil subphase. (From Menger, F. M. and Ellington, A. R., J. Am. Chem. Soc., 112, 8201, 1990. With permission)... 

Gonzaga, R, Perez, E., Rico-Lattes, L, and Lattes, A. 2001. New microemulsions for oxidative decontamination of mustard gas analogues and polymer-thickened half-mustard. New J Chem, 25, 151-155. 

Black, A.T., Joseph, L.B., Casillas, R.P., et al., 2010b. Role of MAP kinases in regulating expression of antioxidants and inflammatory mediators in mouse keratinocytes following exposure to the half mustard, 2-chloroethyl ethyl sulfide. Toxicol. Appl. Pharmacol. 245, 352-360. 

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