Identification of an intact sydnonimine ring depending on the reaction substituents of mesocarb by gas chromatography/mass spectrometry

• Published in: Journal of mass spectrometry. 1999-10, Vol.34 (10), p.1079-1086
• Main Authors: Lee, JeongAe, Jeung, Hyeonsook, Kim, Keon, Lho, Dong-seok
• Format: Article
• Language: English
• Subjects: Analysis; Biological and medical sciences; General pharmacology; intact sydnonimine ring; Medical sciences; mesocarb intermediate; methylated N-nitroso-N-cyanomethylamphetamine; Pharmacology. Drug treatments; pyrolysis; trifluoroacylated sydnophen; trimethylsilylated sydnophen
• ISSN: 1076-5174; 1096-9888
• DOI: 10.1002/(SICI)1096-9888(199910)34:10<1079::AID-JMS869>3.0.CO;2-M

Trifluoroacylated, trimethylsilylated and methylated mesocarb (3‐(1‐methyl‐2‐phenylethyl)‐5‐[[(phenylamino) carbonyl]amino]‐1,2,3‐oxadiazolium) were analyzed by gas chromatography/mass spectrometry (GC/MS). In trifluoroacylation, N‐trifluoroacylated sydnophen (SP‐NTFA), where the exocyclic nitrogen atom of the sydnonimine ring attacks N‐methylbis(trifluoroacetamide), was identified by GC/MS. However, in trimethylsilylation, C‐trimethylsilylated sydnophen (SP‐CTMS), where the C‐4 atom of the sydnonimine ring attacks N‐methyl‐N‐trimethylsilyltrifluoroacetamide, was detected. SP‐NTFA and SP‐CTMS are intermediates of mesocarb in pyrolysis, and retain an intact sydnonimine ring. In methylation, a ketene form of mesocarb reacts as a nucleophile with methyl iodide to produce methylated N‐nitroso‐N‐cyanomethylamphetamine. Thus, depending on the reaction substituents, the intermediate of mesocarb in pyrolysis was identified to be either an intact sydnonimine ring skeleton or an open‐ring compound using GC/MS. Copyright © 1999 John Wiley & Sons, Ltd.