Reference

Nitrosation of some asymmetrical tertiary amines and quaternary ammonium compounds with nitrite or nitrogen dioxide gas

Nitrosation of some asymmetrical tertiary amines and quaternary ammonium compounds with nitrite or nitrogen dioxide gas. Ishibashi, Tohru; Kawabata, Toshiharu; Matsui, Masami (Res. Lab., Japan Med. Food Assoc., Tokyo 203, Japan). Nippon Suisan Gakkaishi, 50(8), 1425-9 (English) 1984. CODEN: NSUGAF. ISSN: 0021-5392. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) The formation of carcinogenic N-nitrosodimethylamine (NDMA) [62-75-9] and asym. alkyl N-nitroso compds. by reacting nitrite or NO2 with asym. tertiary amines N,N-dimethylglycine (DMGly) [1118-68-9], 2-dimethylethanolamine (DMEla) [108-01-0] and quaternary ammonium compds. (betaine [107-43-7], choline [62-49-7], and neurine [463-88-7]) was examd. under varying reaction conditions and the results obtained are summarized. When asym. quaternary ammonium compds. were allowed to react with nitrite in buffer solns. of pH 2.0 or 5.0 at 37° or 90°, no appreciable amts. of NDMA, N-nitrososarcosine (NSAR) [13256-22-9], and N-nitrosomethylethanolamine (NMELA) [26921-68-6] were formed. A high rate of NSAR formation was noted from DMGly, and also a high level of NMELA was formed from DMEla when these amines were allowed to react with nitrite in a buffer soln. of pH 2.0 at 90°; in contrast, rates of these nitrosamines formation apparently decreased when the reactions were allowed to proceed at pH 5.0 and 90°. Concerning nitrosation reaction of amines occurring with NO2 under the conditions of simulated dried squid cooking, no appreciable amt., or only trace quantities of NDMA were formed from sarcosine, DMGly, and betaine, whereas both sarcosine and DMGly gave yields of >1% of NSAR, and that of betaine was ~0.1%.

Prevention of strychnine-induced seizures and death by the N-methylated glycine derivatives betaine, dimethylglycine and sarcosine

Prevention of strychnine-induced seizures and death by the N-methylated glycine derivatives betaine, dimethylglycine and sarcosine. Freed, William J. (Natl. Inst. Ment. Health, Saint Elizabeths Hosp., Washington, DC 20032, USA). Pharmacol., Biochem. Behav., 22(4), 641-3 (English) 1985. CODEN: PBBHAU. ISSN: 0091-3057. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) Betaine (N,N,N-trimethylglycine) [107-43-7], N,N-dimethylglycine [1118-68-9], and sarcosine [107-97-1] antagonize strychnine-induced seizures when administered i.p. The 3 compds. were equipotent, causing a 38-72% decrease in the incidence of seizures and death at a dosage of 5 mmol/kg. Glycine [56-40-6] had no effect. Thus, anticonvulsant activity is conferred to glycine by a single N-methylation.