The HONO-methamphetamine adduct – An unexpected derivative

Nitrosamine formation from the reaction of methamphetamine with gaseous nitrous acid

“…Although little has been published on NMA, nitrosamines are known environmental pollutants with potent carcinogenic properties 21,22 . In their 1983 study, Shimizu et al concluded that NMA showed potent mutagenic properties, also noting its potential as a likely human carcinogen 14 . Over the latter 3 h of the experiments in the current study, there was a steady‐state mass of 4.76 ± 0.07‐μg NMA present on the glass surface in the sample chamber.…”

“…While NMA is not yet a compound of interest in testing standards, previous research has demonstrated that a reaction production from NMA and trifluoroacetic acid anhydride (TFAA) can be detected by GC-MS after using a TFAA derivatisation method that is similar to that commonly employed for methamphetamine testing at suspected former clandestine methamphetamine laboratories. 14 Although NMA has yet to be reported in field samples from suspected former clandestine methamphetamine laboratories or other methamphetamine-contaminated sites, this research demonstrates one likely method of passive formation on NMA within a property.…”

“…With the New Zealand contamination limit for methamphetamine at 1.5 μg/100 cm 2 for areas of frequent use, the higher toxicological hazard of NMA would indicate that an NMA contamination limit would require a more conservative acceptable level than that stated for methamphetamine. While NMA is not yet a compound of interest in testing standards, previous research has demonstrated that a reaction production from NMA and trifluoroacetic acid anhydride (TFAA) can be detected by GC–MS after using a TFAA derivatisation method that is similar to that commonly employed for methamphetamine testing at suspected former clandestine methamphetamine laboratories 14 …”

“…13 Chromatographic analysis of NMA carried out in a previous study in this research group determined that NMA undergoes derivatisation when reacted with trifluoroacetic anhydride, a common derivatisation technique for analysis of surface wipe samples taken from suspected clandestine laboratory sites. 14 These studies indicate the ready formation of NMA from methamphetamine in solution and the ability for it to be detected if present at contaminated sites. If methamphetamine can also undergo heterogeneous oxidation to form nitrosamines, this would demonstrate that there are additional health risks in methamphetamine-contaminated environments, having implications for the safety of current remediation standards for such sites.…”

“…The N ‐nitroso‐derivative of methamphetamine was synthesised from methamphetamine hydrochloride to confirm the presence of the nitrosamine in samples. The synthesis procedure was adapted from Shimizu et al 13 and has been described previously 14 …”