2-Chloroethyl trimethylammonium chloride

The various derivatives of (2-chloroethyl)trimethylammonium chloride have been considered as analogs of choline in which the alcohol group has been designated as X. The general formula of this cation would be CH2X—CH2—N + (CH3) 3. 

The enzyme choline esterase has been shown to have two binding points on its protein surface for these substances—one site for the quaternary ammonium group and one for X. This enzyme catalyzes the hydrolysis of an ester at the X position. From a consideration of the structure of the (2-chloroethyl)trimethylammonium chloride derivatives which were active as plant growth substances, a similar protein-binding site in the plant has been postulated. This site would have a point of attachment for both the ammonium cation and the X constituent of the molecule. This postulated site in the plant is thus similar, but not identical, to cholinesterase, which is an enzyme not known to occur in plants. There is no direct proof for this hypothetical site in the plant. 

Of the derivatives of (2-chloroethyl)trimethylammonium chloride which have been synthesized and tested as plant growth substances for the reduction of the height of plants, numerous substituents at the X site produced derivatives with biological effect (15). The most active derivatives were the chloride or bromide salts of CH0CI-CH0-N+ (CH3)3, CH>Br-CH -N+ (CH3) 3, CHo=CH-CH2-... 

Many compounds have been tested simultaneously with (2-chloroethyl)tri-methylammonium chloride on Thatcher wheat, to ascertain, if possible, whether these chemicals were affecting a particular metabolic process. Other cholinesterase inhibitors such as eserine, diisopropyl fluorophosphate, and nitrogen mustard, neither negated the effect from (2-chloroethyl)trimethylammonium chloride nor altered the growth of the plant themselves. Many other substances were also without effect on the action of (2-chloroethyl)trimethylammonium chloride. A very slight reversal of the alteration by (2-chloroethyl)trimethylam-monium chloride was obtained by 10 2 and 10 3 M choline, betaine, and adenine. Only gibberellin completely and rapidly reversed the shorter growth pattern of a plant which had been treated with (2-chloroethyl)trimethylammonium chloride. 

In some respects, the actions of (2-chloroethyl)trimethylammonium chloride derivatives and MH in altering the growth of plants appear similar. There is no apparent similarity in the chemical structure of maleic hydrazide,... 

N-2-chloroethyl-trimethylammonium chloride = N-dimethylmorpholinium chloride = N-dimethylpiperidinium chloride = S-dimethyl-isopropylsulfonium bromide = S-methylthianium bromide = S-2,5-dimethyl-4-pentamethylenecarbamoyl-... 

CHLOROETHYL SULPHITE of l-(p-tert-BUTYLPHENOXY)-2-PROPANOL see SOPSOO l-CHLORO-2-(ETHYLTHIO)ETHANE see CGY750 (2-CHLOROETHYL)TRIMETHYLAMMONIUM CHLORIDE see CMF400 (P-CHLOROETHYL)TRIMETHYLAMMONIUM CHLORIDE see CMF400... 

In 1969, Knypl (10) found that an onium compound, chlorme-quat [(2-chloroethyl)-trimethylammonium chloride], caused all-trans-lycopene accumulation in detached pumpkin (Curcubita pepo) cotyledons. However, no such response was observed when chlorme-quat was applied to other plant tissues (11). A major step forward was observed in 1970 with the discovery that another onium compound, 2-(4-chlorophenylthio)-triethylammonium chloride (CPTA), can cause the accumulation of lycopene in a wide array of plant tissues and microorganisms (11). 

An ionic liquid can be formed by adding ZnCl2 to (2-chloroethyl)trimethylammonium chloride, XCl. When the ratio of ZnCl2 XCl = 2 1, fast atom bombardment mass spectrometry shows the presence of [ZiixC yY ions with m/z = 171, 307 and 443. Suggest identities for these ions and write a series of equilibria to account for their formation. 

A more interesting herbicide from the viewpoint of lipid metabolism is (2-chloroethyl)trimethylammonium chloride (CCC), a choline analogue. This compound decreases intemodal elongation, but its effect is completely negated by gibberellin. Effects of CCC last for several weeks, but to some extent it can be converted to choline in the plant (Schneider, 1967), and as such incorporated into PC (Willemot and Belzile, 1970). Tanaka and Tolbert (1966) found that CCC stimulated the partially purified choline kinase from leaves. When [ K2]choline was fed to barley or wheat roots, CCC stimulated incorporation into lipids. These effects were reversed by gibberellin. 

Chlormequat. See Chlormequat chloride Chlormequat chloride CAS 999-81-5 EINECS/ELINCS 213-666-4 Synonyms CCC Chlorcholine chloride Chlormequat Chlorocholine chloride 2-Chloroethyltrimethylammonium chloride 2-Chloroethyl-N,N,N-trimethyl ammonium chloride (P-Chloroethyl) trimethylammonium chloride 2-Chloro-N,N,N-trimethylethanaminium chloride Choline dichloride Ethanaminium, 2-chloro-N,N,N-trimethyl-, chloride... 

More recently, microemulsions have been developed for the oxidative/hydrolytic destruction of sulfanes sulfoxides) and phosphoric acid derivatives using sodium hypochlorite and cetyl-trimethylammonium chloride (CTAC). The compounds studied serve as model compounds for chemical warfare agents such as mustard gas [bis(2-chloroethyl)sulfane] and sarin (GB i-propyl-methylphosphonofluoridate). Big stocks of these must now be destroyed after implementation of the Chemical Weapons Convention (CWC), which came into force in April 1997 [865],... 

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